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Sökning: WFRF:(Xie Yongshu)

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1.
  • Baryshnikov, Gleb V., et al. (författare)
  • Computational study of aromaticity, H-1 NMR spectra and intermolecular interactions of twisted thia-norhexaphyrin and its multiply annulated polypyrrolic derivatives
  • 2019
  • Ingår i: Physical Chemistry, Chemical Physics - PCCP. - : ROYAL SOC CHEMISTRY. - 1463-9076 .- 1463-9084. ; 21:45, s. 25334-25343
  • Tidskriftsartikel (refereegranskat)abstract
    • The recently synthesized twisted thia-norhexaphyrin and its multiply annulated polypyrrolic derivatives have been studied computationally. Gauge-including magnetically induced current calculations predict a global nonaromatic character of the initial thia-norhexaphyrin due to the highly-twisted conformation of the macrocycle. Upon the oxidation of the thia-norhexaphyrin four multiply annulated polypyrrolic aromatic macrocycles are formed for which the global aromatic character is confirmed in agreement with experimentally measured H-1 NMR spectra. The calculation of the proton chemical shifts for the studied compounds by direct comparison with the tetramethylsilane standard leads to a significant mean absolute error. At the same time a linear regression procedure for the two selected groups of protons (CH and NH protons) provides much better values of calculated chemical shifts and tight correlation with experiment. The separate consideration of NH protons is motivated by the numerous intermolecular hydrogen bonds in which the protons are involved, which induce considerable upfield shifts, leading to a significant underestimation of the corresponding chemical shifts. Such a selected correlation can be used for accurate estimation of proton chemical shifts of the related porphyrinoids. Bader's theory of Atoms in Molecules has been applied for the studied twisted thia-norhexaphyrin and its multiply annulated polypyrrolic derivatives to characterize intramolecular H-bonds and other non-covalent interactions.
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2.
  • Cao, Guanyue, et al. (författare)
  • Porphyrindiene-Based Tandem Diels-Alder Reaction for Preparing Low-Symmetry pi-Extended Porphyrins with Push-Pull Skeletons
  • 2022
  • Ingår i: Journal of Organic Chemistry. - : AMER CHEMICAL SOC. - 0022-3263 .- 1520-6904. ; 87:14, s. 9001-9010
  • Tidskriftsartikel (refereegranskat)abstract
    • Tandem Diels-Alder reactions of masked porphyrindienes (i.e., sulfolenoporphyrins) with benzoquinones and stilbenes, followed by aromatization, have been developed to load porphyrin with mixed annulation units (i.e., terphenyl and naphthoquinone), furnishing the low-symmetry pi-extended porphyrins (DxAy) with push-pull skeletons. All low-symmetrical chromophores display panchromatic absorption spectra, which look like a spectral combination of symmetrical congeners (D4/A4) in a certain ratio. Among them, tD2A2 with trans-arrangement of push/pull units possesses the largest maximum centered at 766 nm with the onset around 900 nm. The fusion of the electron-deficient naphthoquinone moiety on the porphyrin core results in the approximately quantitative regulation of the E-ox1 and HOMOs (i.e., 0.10-0.13 V increase for the E-ox1 and 0.14-0.16 eV decrease for the HOMOs per naphthoquinone unit). In brief, this work provides a new way to construct low-symmetry pi-extended porphyrins with tunable properties resorting to the ratios and locations of the annulated push-pull units.
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3.
  • Chen, Bin, et al. (författare)
  • A novel trigeminal zinc porphyrin and corresponding porphyrin monomers for dye-sensitized solar cells
  • 2014
  • Ingår i: RSC Advances. - : Royal Society of Chemistry (RSC). - 2046-2069. ; 4:21, s. 10439-10449
  • Tidskriftsartikel (refereegranskat)abstract
    • A novel trigeminal zinc porphyrin sensitizer (T) and two zinc porphyrin monomers (M1 and M2) were successfully designed and synthesized. The spectral, electrochemical, and photovoltaic properties of the porphyrin dyes were investigated. Compared with M1, the molecule of M2 has an additional aliphatic n-hexyloxyl chain at the meso-position of the porphyrin framework, and such a structure is favorable for the formation of a compact hydrophobic layer at the TiO2 surface and the retardation of the diffusion of I-3(-) ions into the nanoporous TiO2 electrode, resulting in more effective suppression of the charge recombination process and a higher V-oc. Meanwhile, M2 has larger IPCE values than those of M1, leading to the higher J(sc) value. Thus, the DSSC devices based on M2 demonstrated a relatively high power conversion efficiency of 5.77%, with the J(sc), V-oc and ff values of 13.93 mA cm(-2), 732 mV, and 0.566, respectively. Even though dye T has the highest molar absorption coefficients and multiple binding moieties, the corresponding power conversion efficiency is 2.30%, which is lower than those for M1 and M2. These observations may be ascribed to the low efficiency of the electron injection process caused by the isolation of the LUMOs from the anchoring carboxyl groups in addition to the lowest adsorption amount.
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4.
  • Chen, Bin, et al. (författare)
  • Full-colour luminescent compounds based on anthracene and 2,2 '-dipyridylamine
  • 2013
  • Ingår i: Journal of Materials Chemistry C. - : Royal Society of Chemistry (RSC). - 2050-7526 .- 2050-7534. ; 1:44, s. 7409-7417
  • Tidskriftsartikel (refereegranskat)abstract
    • Starting from two simple units of anthracene and 2,2'-dipyridylamine, a series of new luminescent compounds 1-8 were designed and synthesized by a combined strategy of changing the connection mode between the two units, extending the conjugation size, and introducing an additional electron donor. Photophysical properties of 1-8 were investigated and discussed on the basis of solvatochromic behaviour, theoretical calculations, crystal structure, and optimized structures. Interestingly, the emission wavelengths of these compounds could be successfully tuned from violet to red both in solutions and the solid-state, and prominent positive solvatochromism was observed for the compounds with a D-p-A framework. Consider compound 7 as an example, it shows peaks at 526 nm and 627 nm in cyclohexane and DMSO, respectively. Meanwhile, the quantum yield was decreased from 0.80 in cyclohexane to 0.12 in DMSO. The introduction of bulky groups was demonstrated to be effective for suppressing the aggregation effect and thus improving the solid state emission quantum yield. These results indicate that the combined structure modulation strategy offers a powerful tool for tuning the emission behaviour. To demonstrate the possibility of practical applications, 2 was employed as the emitting material for the fabrication of deep-blue organic light-emitting diodes (OLEDs), which showed a maximum external quantum efficiency of 2.2%. The CIE coordinates of (0.15, 0.08) are indicative of excellent blue color purity.
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5.
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6.
  • Chen, Bin, et al. (författare)
  • TICT based fluorescence "turn-on" hydrazine probes
  • 2014
  • Ingår i: Sensors and actuators. B, Chemical. - : Elsevier BV. - 0925-4005 .- 1873-3077. ; 199, s. 93-100
  • Tidskriftsartikel (refereegranskat)abstract
    • Fluorescence "turn-on" probes PC3 and C3 with weak background emissions were developed for hydrazine sensing. The aldehyde and dicyanovinyl groups were used as the recognition units for PD and C3, respectively. Because of low reactivity of the aldehyde group, the fluorescence of PC3 was enhanced by only ca. 93 folds upon addition of a large amount of 1646 eq. hydrazine. In contrast, 0 exhibited fluorescence enhancement by ca. 239 folds upon addition of only 1.3 eq. hydrazine, and thus it showed high sensitivity towards hydrazine, with the detection limit of 7 ppb. In aqueous systems, it also works well with improved selectivity for hydrazine over CN-. The weak fluorescence of PC3 and 0 can be ascribed to twisted intramolecular charge transfer (TICT) processes by the combination of the bulky diphenylamino and 9-anthryl units, which were well demonstrated by theoretical calculations, viscosity dependent fluorescence, and fluorescence decay behaviour. Addition of hydrazine induced the disappearance of the TICT deactivation pathway, resulting in the observed fluorescence enhancement. It can be concluded that the combination of the bulky diphenylamino and 9-anthryl units is an effective approach for developing fluorescence turn-on hydrazine probes based on the TICT mechanism.
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7.
  • Chen, Yingying, et al. (författare)
  • Fluorenyl Indoline as an Efficient Electron Donor for Concerted Companion Dyes: Enhanced Light-Harvesting and Photocurrent
  • 2021
  • Ingår i: ACS Applied Materials and Interfaces. - : AMER CHEMICAL SOC. - 1944-8244 .- 1944-8252. ; 13:42, s. 49828-49839
  • Tidskriftsartikel (refereegranskat)abstract
    • Concerted companion dyes (CC dyes) like XW61 have been demonstrated to be an effective platform for developing efficient DSSCs. However, the moderated phenothiazine-based electron donor in XW61 results in unsatisfactory J(sc). To address this problem, a stronger fluorenyl indoline-based electron donor has been used to construct porphyrin dye XW68 and organic dyes Y1-Y2. The stronger electron-donating character of the fluorenyl indoline unit leads to an enhanced J(sc) value (20.48 mA.cm(-2)) for the individual dye XW68. On this basis, CC dyes XW69-XW70-C8 have been designed and synthesized by combining the frameworks of Y1 and Y2 with XW68. The complementary absorption characters of the porphyrin and the organic dye moieties lead to panchromatic absorption with a strong light-harvesting capability from 350 to 700 nm and the onset wavelength extended to ca. 840 nm in the IPCE curves. As a result, excellent J(sc) values have been achieved (>22 mA.cm(-2)). In addition to the advantages of high J(sc), bulky octyl groups have been introduced into the donor of XW70-C8 to reduce dye aggregation and suppress charge recombination. Finally, a highest PCE of 11.1% with a satisfactory J(sc) (22.25 mA.cm(-2)) and an enhanced V-oc (750 mV) has been achieved upon coadsorption of XW70-C8 with CDCA. In addition, the CC dye XW70-C8-based solar cells exhibit excellent long-term photostability. These results provide an effective method for rationally improving the photovoltaic behavior, especially the J(sc) of CC dyes, by introducing strong electron donor moieties with suitable substituents.
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8.
  • Ding, Yubin, et al. (författare)
  • Acid/Base Switching of the Tautomerism and Conformation of a Dioxoporphyrin for Integrated Binary Subtraction
  • 2014
  • Ingår i: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 20:40, s. 12910-12916
  • Tidskriftsartikel (refereegranskat)abstract
    • Compared with most of the reported logic devices based on the supramolecular approach, systems based on individual molecules can avoid challenging construction requirements. Herein, a novel dioxoporphyrin DPH22 was synthesized and two of its tautomers were characterized by single-crystal X-ray diffraction studies. Compound DPH22 exhibits multichannel controllable stepwise tautomerization, protonation, and deprotonation processes through interactions with H and F- ions. By using the addition of H+ and F- ions as inputs and UVNis absorption values at.1=412, 510, 562, and 603 nm as outputs, the controlled tautomerism of DPH22 has been successfully used for the construction of an integrated molecular level half-subtractor and comparator. In addition, this acid/base-switched tautomerism is reversible, thus endowing the system with ease of reset and recycling; consequently, there is no need to modulate complicated intermolecular interactions and electron-/chargetransfer processes.
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9.
  • Ding, Yubin, et al. (författare)
  • alpha-Monoacylated and alpha,alpha '- and alpha,beta '-Diacylated Dipyrrins as Highly Sensitive Fluorescence "Turn-on" Zn2+ Probes
  • 2013
  • Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 78:11, s. 5328-5338
  • Tidskriftsartikel (refereegranskat)abstract
    • With the purpose of developing readily synthesized CHEF (chelation-enhanced fluorescence) type Zn2+ probes with relatively simple molecular structures and excellent sensing behavior, p-anisoyl chloride was used for the acylation of 5-(pentafluorophenyl)dipyrromethane. Interestingly, the alpha,beta'-diacylated product PS2 with a unique substitution mode was obtained in high yield in addition to the normal a-substituted mono- and diacylated products PSI and PS3. Further oxidation of PS1-PS3 afforded dipyrrins S1-S3. Crystal structure and H-1 NMR measurements of S2 demonstrate the existence of a pure tautomer, which is consistent with DFT calculations. S1-S3 show highly Zn2+ selective "turn-on" fluorescence based on a CHEF mechanism by the formation of 2:1 (probe:metal) Zn2+ complexes. The emission colors can be easily tuned from green to red by changing the dipyrrin substitution modes. Furthermore, these probes demonstrate fast responses and wide applicable pH ranges. Among them, S2 shows the highest Zn2+ sensitivity, with a detection limit of 4.4 x 10(-8) M.
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10.
  • Ding, Yubin, et al. (författare)
  • From nonconjugation to conjugation : novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes
  • 2013
  • Ingår i: Organic and biomolecular chemistry. - : Royal Society of Chemistry (RSC). - 1477-0520 .- 1477-0539. ; 11:16, s. 2685-2692
  • Tidskriftsartikel (refereegranskat)abstract
    • Most reported Zn2+ probes suffer from the interference of background fluorescence originated from the conjugated structures of commonly utilized fluorophores. In this work, three novel meso-hydroxyl group substituted dipyrromethanes DPMOH1-DPMOH3 were synthesized and found to be colourless and nonfluorescent due to the interruption of the conjugated p system by an sp(3) carbon between the two pyrrolic units. Interestingly, only the addition of Zn2+ to the solutions of DPMOH1-DPMOH3 promoted their oxidation to dipyrrin forms, and bright fluorescence "turn on" was observed due to the formation of corresponding dipyrrin complexes with the dipyrrin : zinc stoichiometry of 2 :1. Zn2+ detection mechanism was investigated by UV-Vis, fluorescence, H-1 NMR and HRMS analyses, which can be ascribed to the CHEF type fluorescence enhancement, resulting from good rigidity of the dipyrrin complexes. Hence, DPMOH1-DPMOH3 can be used as fluorescence turn-on Zn2+ probes with the advantage of no background fluorescence.
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11.
  • Du, Yu, et al. (författare)
  • N-Confused Hexapyrrolic Phlorinoid with NIR Absorption : Synthesis, Fusion, Oxidation, and Copper(II) Coordination
  • 2020
  • Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 22:24, s. 9648-9652
  • Tidskriftsartikel (refereegranskat)abstract
    • An N-confused hexapyrrolic phlorinoid 1 and its isomer N-fused hexapyrrolic phlorinoid 2 were synthesized through [4 + 2] condensation. Both 1 and 2 can be readily transformed into N-confused hexapyrrolic phlorinone 3 under aerobic conditions. Coordination of 1 with Cu(acac)(2) afforded two different mono-Cu(II) complexes 4 and 5 with CNNN and ONNN coordination environments, respectively. The NIR absorption bands can be effectively modulated up to 1265 nm through the oxidation, fusion, and metalation reactions.
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12.
  • Fu, Yating, et al. (författare)
  • Rational Synthesis of 5,5,5-Tricyclic Fused Thia-heptaphyrin (1.1.1.1.1.1.0) From a Helical Oligopyrrin Hybrid
  • 2020
  • Ingår i: Chemistry - An Asian Journal. - : WILEY-V C H VERLAG GMBH. - 1861-4728 .- 1861-471X. ; 15:8, s. 1285-1289
  • Tidskriftsartikel (refereegranskat)abstract
    • Oxidation of a thiophene-hexapyrrane hybrid S-P-6 afforded a stable conjugated open-chain thiaheptapyrrolic helix 1 with the terminal thiophene and confused pyrrole units lying at a long distance that is adverse for further cyclization. Chelation of 1 with copper(II) ion afforded 1-Cu, which exhibits more distant terminal units. Interestingly, further oxidation of 1 triggered an intramolecular C-N fusion reaction to afford a unique 5,5,5-tricyclic fused linear thiaheptapyrrin 2, with the two terminals positioned in proximity, which favors the oxidative ring-closure reaction to give a unique 5,5,5-tricyclic fused thiaheptaphyrin (1.1.1.1.1.1.0) 3 under air. The inner-fusion strategy for positioning the reactive sites in proximity to promote oxidative cyclization offers a new approach for constructing large porphyrinoids through conjugated oligopyrrins without the assistance of metal ions.
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13.
  • Gao, Shimin, et al. (författare)
  • Stable thiophene-embedded N-confused homoporphyrins : Partial conjugation, fusion and fluoride binding
  • 2021
  • Ingår i: Dyes and pigments. - : Elsevier. - 0143-7208 .- 1873-3743. ; 194
  • Tidskriftsartikel (refereegranskat)abstract
    • In the past decades, porphyrin analogues have attracted increasing attention in light of their unique properties and potential applications in various areas. In this work, novel nonconjugated thiophene-embedded N-confused homoporphyrins 1 and 2 as well as a fully-conjugated N-fused homoporphyrin 3 have been prepared through acid-catalyzed condensation reactions followed by oxidation. Both 1 and 2 comprise two meso-sp3-carbon atoms. However, they are insensitive to the air or common oxidants. Single crystal X-ray diffraction analysis reveals that 2 adopts a highly distorted boat-like conformation, with the NH moieties of two pyrrolic units pointing outwards and an O atom attached to the alpha position of the N-confused pyrrole unit. As a result, hydrogen-bonded dimers are formed through the intermolecular hydrogen bonds between the lactam-like moieties. In contrast to the highly distorted structure of 2, N-fused homoporphyrin 3 contains a unique 5,5,5-tricyclic fused ring, and thus demonstrates a relatively coplanar conformation except one inverted pyrrole unit. Because of the different structural characters, 3 exhibits F- binding behavior distinct from that of 1 and 2.
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14.
  • Gao, Shimin, et al. (författare)
  • Syntheses of thiophene appended N-confused phlorin isomers
  • 2021
  • Ingår i: Journal of Porphyrins and Phthalocyanines. - : World Scientific Pub Co Pte Ltd. - 1088-4246 .- 1099-1409. ; 25:10N12, s. 997-1003
  • Tidskriftsartikel (refereegranskat)abstract
    • A doubly confused thiapentapyrrane NSP-5 was synthesized by acid-catalysed condensation. Subsequent oxidation with DDQ did not afford the expected thiasapphyrin-like product. Instead, two tetrapyrrolic macrocycles, i.e. neo-N-confused phlorin (1) and N-confused phlorin-II (2) were obtained in the yields of 14% and 18%, respectively. The compounds were characterized by NMR, HRMS, and X-ray diffraction analyses. Single crystal structures clearly reveal that the thienyl units are not embedded into the macrocycles, but appended as meso-substituents, and the C-meso-N and C-meso-C-beta cyclization modes can be clearly revealed by the crystal structures of 1 and 2, respectively. The observation that the thienyl unit is not involved in oxidative cyclization may be related to the relatively low reactivity of the thiophene moiety compared with the more electron-rich pyrrole unit. These results indicate that oxidative cyclization of linear thiaoligopyrranes containing terminal thiophene units may be developed as an effective approach for synthesizing nonconjugated macrocycles like phlorin analogues.
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15.
  • Gao, Shimin, et al. (författare)
  • Synthesis, characterization, and spectroscopic properties of 2-(3,5,6-trichloro-1,4-benzoquinon-2-yl)-neo-fused hexaphyrin
  • 2021
  • Ingår i: Bulletin of the Korean Chemical Society (Print). - : John Wiley & Sons. - 0253-2964 .- 1229-5949. ; 42:12, s. 1569-1573
  • Tidskriftsartikel (refereegranskat)abstract
    • In this work, a novel compound 2-(3,5,6-trichloro-1,4-benzoquinon-2-yl)-neo-fused hexaphyrin has been prepared from tetrachloroquinone and neo-fused hexaphyrin through a substitution reaction. The chemical structure of the compound has been characterized by nuclear magnetic resonance (NMR), high-resolution mass spectrum, UV-Vis spectrum, and X-ray diffraction. The crystal structure reveals that the quinonyl unit is almost coplanar with the adjacent N-confused pyrrole unit. Because of the cooperative effect of extended conjugation and the intramolecular charge transfer effect related to the strong electron-withdrawing character of the quinonyl unit, the absorption of 2 is dramatically extended to ca. 1280 nm.
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16.
  • He, Yixing, et al. (författare)
  • Chain Length Modulated Dimerization and Cyclization of Terminal Thienyl-Blocked Oligopyrranes
  • 2022
  • Ingår i: Organic Letters. - : AMER CHEMICAL SOC. - 1523-7060 .- 1523-7052. ; 24:29, s. 5428-5432
  • Tidskriftsartikel (refereegranskat)abstract
    • Oxidation of thienyl-blocked bilane and pentapyrrane afforded chain length dependent products of the symmetric dimer D1 and the thienyloligopyrrin-appended pentaphyrin analogue P2, respectively, with the latter formed by simultaneous dimerization and cyclization. Coordination of D1 and P2 with Cu(II) afforded di-and monometallic complexes D1-Cu2 and P2 -Cu, respectively. These compounds exhibit distinct NIR absorption, with the absorption tail of D1-Cu2 extended to ca. 1900 nm despite its smaller conjugation framework than that of P2 -Cu.
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17.
  • Hong, Tao, et al. (författare)
  • Syntheses of mono- and diacylated bipyrroles with rich substitution modes and development of a prodigiosin derivative as a fluorescent Zn(II) probe
  • 2014
  • Ingår i: RSC Advances. - : Royal Society of Chemistry (RSC). - 2046-2069. ; 4:12, s. 6133-6140
  • Tidskriftsartikel (refereegranskat)abstract
    • The acylation of 2,20-bipyrrole with pentafluorobenzoyl chloride in the presence of AlCl3 afforded six acylated products with rich alpha-, beta-, beta(1)-, alpha,alpha'-, alpha,beta(')-, and alpha,beta(1)'-substitution modes for 1-6, respectively. Then, the alpha,alpha'-diacylated compound 4 was used to synthesize a prodigiosin derivative 9, which provides an alternative method for the syntheses of prodigiosin derivatives. Crystal structures of 1, 4 and 9 show interesting supramolecular dimers formed by multiple hydrogen bonds, O...pi interactions, as well as pi... pi interactions. Interestingly, 9 shows fluorescence turn-on probing behavior towards Zn2+ both in DMF and in DMF-HEPES, with high sensitivity and selectivity. The detection limit for Zn2+ in DMF was calculated to be 1.1 x 10(-8) M.
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18.
  • Huang, Yanping, et al. (författare)
  • Syntheses and characterization of dithienyl-blocked hexapyrrin and its mononuclear complexes
  • 2023
  • Ingår i: Journal of Porphyrins and Phthalocyanines. - : World Scientific. - 1088-4246 .- 1099-1409. ; 27:07N10, s. 1089-1096
  • Tidskriftsartikel (refereegranskat)abstract
    • With the purpose to develop long chain-conjugated oligopyrrin-like compounds and their metal complexes, and thus achieve tunable near-infrared absorption, a dithienyl-blocked hexapyrrane S-2-P-6 was synthesized by acid-catalyzed [2+4+2] condensation, followed by oxidation with DDQ to afford dithiaoctapyrrin 1, and its mononuclear metal complexes 1-Cu and 1-Zn were synthesized by treating 1 with Cu(II) and Zn(II) acetates. All the compounds were systematically characterized by NMR/EPR, and HRMS. The crystal structures revealed that 1 adopts a double hook-like conformation. Whereas, both complexes 1-Cu and 1-Zn adopt spiral-hook hybrid conformations, showing smaller interplanar angles between the rings within the spiral part, compared with those in the hook-like counterpart of molecule 1, which is favorable for red-shifting the absorption. As expected, the absorption band edges for complexes 1-Cu and 1-Zn are red-shifted to ca. 1560 nm, compared with that of 1260 nm observed for 1.
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19.
  • Huang, Yanping, et al. (författare)
  • Syntheses and coordination of linear and macrocyclic pentapyrroles possessing a fused moiety : Confusion modulated structural diversity
  • 2024
  • Ingår i: Dyes and pigments. - : Elsevier. - 0143-7208 .- 1873-3743. ; 223
  • Tidskriftsartikel (refereegranskat)abstract
    • Porphyrinoids have attracted wide interest because of their vital roles in biological processes and fascinating structural and functional characters. In this work, a doubly N-confused pentapyrrane precursor N2C–P5 has been synthesized with terminal pyrrole ring A and middle pyrrole C incorporated in the N-confused mode. On this basis, pentapyrrin 1 and sapphyrin 2 have been synthesized by oxidizing N2C–P5 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Both 1 and 2 possess a [5.5.5]-tricyclic fused ring involving pyrrole B and the neighboring confused pyrrole C. Meanwhile, the formation of 2 involves ring closure between the terminal rings A and E. Notably, 2 exists as a diradical showing a half-field signal in the electron paramagnetic resonance (EPR) spectrum and a singlet ground state with a negative singlet-triplet energy gap of −0.50 kcal/mol. Excellent thermal stability has been observed for 2, which may be related to its large π-conjugated framework involving the fused structure. On this basis, 1 and 2 were treated with Cu(acac)2 to afford Cu(II) complexes 3 and 4, respectively. As a result, an acetylacetonyl moiety is attached at the terminal pyrrole ring E to afford an NNNO coordination environment for complex 3, and the sapphyrin macrocycle of 2 has been cleaved between rings A and B to afford a fused pentapyrrin ligand, furnishing an NNNN coordination environment for complex 4, in which a pentafluorophenyl-ketal group generated during the ring cleavage reaction is attached to ring A, and it can be hydrolyzed to the corresponding pentafluorobenzoyl substituent to afford complex 5. Compared with free bases 1 and 2, complexes 3−5 show more intense low-energy near-infrared (NIR) absorption bands at ca. 791, 926 and 907 nm, respectively. This work provides an effective approach for the syntheses of linear and macrocyclic oligopyrroles with intriguing structures and properties by oxidizing oligopyrranes with precisely designed numbers and positions of N-confused pyrroles.
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20.
  • Kong, Jiahui, et al. (författare)
  • Modulation of the structures and properties of bidipyrrin zinc complexes by introducing terminal alpha-methoxy groups
  • 2017
  • Ingår i: Dyes and pigments. - : Elsevier. - 0143-7208 .- 1873-3743. ; 137, s. 430-436
  • Tidskriftsartikel (refereegranskat)abstract
    • A bidipyrrin nickel complex was synthesized in a high yield by oxidatively coupling between the ligands in the corresponding 2:1 (L:M) type of dipyrrin nickel complex, and further demetallation afforded the free bidipyrrin ligand. Interestingly, when treating the bidipyrrin nickel complex or the free bidipyrrin with FeCl3 in CH2Cl2/MeOH, the symmetric di-alpha-methoxy bidipyrrin could be synthesized in a high yield, with two methoxy groups attached to the terminal pyrrolic alpha-positions. Moreover, the coordination of the unsubstituted and disubstituted bidipyrrins with Zn(OAc)(2),2H(2)O afforded two similar M2L2 type of bidipyrrin helical complexes with different ligand conformations and different Zn center dot center dot center dot Zn distances of 5.353 and 3.357 angstrom, respectively. The difference in the conformations may be related to the electrostatic repulsions between the methoxy substituents. These results indicate that the dyes based on helical bidipyrrin zinc complexes with tunable structures and photophysical properties may be developed simply by modulating the terminal alpha-substituents.
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21.
  • Kong, Jiahui, et al. (författare)
  • Tetra- and Octapyrroles Synthesized from Confusion and Fusion Approaches
  • 2016
  • Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 18:19, s. 5046-5049
  • Tidskriftsartikel (refereegranskat)abstract
    • By oxidation of an alternately N-confused bilane in CH2Cl2, a C-N fused tetrapyrrin was synthesized that bears a 5.5.5-tricyclic ring generated from an intramolecular C-N linkage. When CH3CN was used as the reaction medium, a multiply C-N-fused octapyrrolic dimer was also obtained that contained two 5.5.5.7.5-pentacyclic moieties and a bipyrrole unit generated from the intramolecular C-N linkage and intermolecular C-C linkage, respectively. This could be coordinated with Ni(acac)(2) to afford a mixed-ligand complex.
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22.
  • Li, Chengjie, et al. (författare)
  • Expanded N-Confused Phlorin : A Platform for a Multiply Fused Polycyclic Ring System via Oxidation within the Macrocycle
  • 2020
  • Ingår i: Journal of the American Chemical Society. - : American Chemical Society (ACS). - 0002-7863 .- 1520-5126. ; 142:40, s. 17195-17205
  • Tidskriftsartikel (refereegranskat)abstract
    • Novel interrupted pi-conjugated macrocycles derived from expanded porphyrinoids were synthesized, and their unique reactivity was investigated in this work. The specific porphyrin analogs, so-called phlorins and isoporphyrins, possess a meso-sp(3) methylene moiety, showing inner 3NH and 1NH pyrrolic cores, respectively, and extended near-infrared (NIR) absorption. Expanded N-confused pentapyrrolic phlorin analog 1 bears an interrupted cyclic pi-conjugated system that is featured by a distinct higher HOMO and a lower LUMO. Oxidation of 1 allowed structural transformations through the expanded isoporphyrin-like species 2. One of the representative products is a spiro-carbon-bridged multiply N-fused product 3 comprising a fused [5.6.5.7.6.5]-hexacyclic ring obtained by oxidation with 2,3-dichloro-5,6-dicyano-p-benzoquinone. When magic blue was used as the oxidant, an aromatic N-confused pentaphyrin 4 was obtained via migration of one of the meso-phenyl groups to the beta-position of the neighboring pyrrolic ring. By employing the flexible cavity of 1 for metal coordination, Pd(II) complexation occurred with a specific meso oxygenation to give a bimetallic complex 5. In contrast to the rich oxidation reactions, reduction of 1 with NaBH4 resulted in the regioselective nucleophilic hydrogen substitution reaction at the para position of one of the meso-C6F5 groups. These results provide a practical approach for synthesizing novel interrupted or aromatic pi-conjugated frameworks showing NIR absorptions.
  •  
23.
  • Li, Chengjie, et al. (författare)
  • Tripyrrin-armed isosmaragdyrins : synthesis, heterodinuclear coordination, and protonation-triggered helical inversion
  • 2020
  • Ingår i: Chemical Science. - : ROYAL SOC CHEMISTRY. - 2041-6520 .- 2041-6539. ; 11:10, s. 2790-2795
  • Tidskriftsartikel (refereegranskat)abstract
    • Oxidative ring closure of linear oligopyrroles is one of the synthetic approaches to novel porphyrinoids with dinuclear coordination sites and helical chirality. The spatial arrangement of the pyrrolic groups of octapyrrole (P8) affected the position of the intramolecular oxidative coupling of the pyrrolic units; tripyrrin-armed isosmaragdyrin analogue (1) containing a beta,beta-linked bipyrrole moiety was synthesized regioselectively in a high yield by using FeCl3. Ni-II-coordination at the armed tripyrrin site of 1 allowed the formation of diastereomeric helical twisted complexes (2A and 2B) and succeeding Cu-II-coordination at the macrocyclic core afforded heterodinuclear Ni-II/Cu-II-complexes (3A and 3B). Each of them comprised a pair of separable enantiomers, exhibiting P- and M-helices, respectively. Notably, diastereomeric interconversion from 2A to 2B was quantitatively achieved as a consequence of helical transformation under acidic conditions.
  •  
24.
  • Li, Mengyuan, et al. (författare)
  • Pd(II) and Cu(III) Complexes of Multiply Fused Pentaphyrin Isomers with Tunable Structures and NIR Absorption
  • 2024
  • Ingår i: Inorganic Chemistry. - : AMER CHEMICAL SOC. - 0020-1669 .- 1520-510X. ; 63:29, s. 13392-13401
  • Tidskriftsartikel (refereegranskat)abstract
    • Fused porphyrinoids have received increasing interest in light of their extended conjugation and unique coordination behavior. On the basis of our previously reported multiply fused pentaphyrin isomers 1 and 2, a novel isomer 3 has been synthesized in this work. 3 possesses a hexacyclic fused moiety with a nearly coplanar CCNN cavity involving an inverted pyrrole, which is slightly different from the CNNN ones of 1 and 2 involving an N-confused pyrrole. 1-3 possess cavities with three depronatable protons and thus they all can generate Cu(III) complexes. However, only 3Cu is stable under ambient conditions. On the other hand, 3 remains intact upon treatment with Pd(II) ions, while 1 and 2 could undergo structural rearrangement to accommodate Pd(II), affording 1Pd and 2Pd accompanied by the formation of a lactone ring and the addition of a methoxy group, respectively. Compared with the free bases, the complexes show distinct aromaticity and more intense near-infrared (NIR) absorption up to ca. 1600, 1170, and 1500 nm, respectively. The results indicate that the subtle modification of the linking modes between the pyrrolic units in the fused pentaphyrinoids is effective in modulating the coordination behavior for synthesizing complexes with tunable aromaticity and NIR absorption.
  •  
25.
  • Li, Qizhao, et al. (författare)
  • Antiaromatic Sapphyrin Isomer : Transformation into Contracted Porphyrinoids with Variable Aromaticity
  • 2023
  • Ingår i: Angewandte Chemie International Edition. - : Wiley-VCH Verlagsgesellschaft. - 1433-7851 .- 1521-3773. ; 62:1
  • Tidskriftsartikel (refereegranskat)abstract
    • Sapphyrin is a pentapyrrolic expanded porphyrin with a 22π aromatic character. Herein, we report the synthesis of a 20π antiaromatic sapphyrin isomer 1 by oxidative cyclization of a pentapyrrane precursor P5 with a terminal β-linked pyrrole. The resulting isomer 1, containing a mis-linked bipyrrole unit in the skeleton, exhibits a reactivity for further oxidation due to the distinct antiaromatic electronic structure, affording a fused macrocycle 2, possessing a spiro-carbon-containing [5.6.5.6]-tetracyclic structure. Subsequent treatment with an acid afforded a weakly aromatic pyrrolone-appended N-confused corrole 3, and thermal fusion gave a [5.6.5.7]-tetracyclic-ring-embedded 14π aromatic triphyrin(2.1.1) analog 4. The cyclization at the mis-linked pyrrole moiety of P5 played a crucial role in synthesizing the antiaromatic porphyrinoid susceptible to facile transformation to novel porphyrinoids with variable aromaticity.
  •  
26.
  • Li, Qizhao, et al. (författare)
  • Conformation Governed Reactivity of Fused Thia-Sapphyrin Dimers Bearing Multiply Fused Heteroaromatic Rings
  • 2023
  • Ingår i: CCS CHEMISTRY. - : Chinese Chemical Society. - 2096-5745. ; 5:6, s. 1332-1342
  • Tidskriftsartikel (refereegranskat)abstract
    • Suitable conformations and proper alignment of complex natural macrocycles are essential for achieving their unique properties. However, such artificial macrocycle prototypes are still limited due to synthetic difficulties. In this respect, directly linked porphyrin analog dimers display tunable conformations and intriguing properties, and thus, they may be employed as a class of promising platforms. Herein, we report that one-pot oxidative dimerization of thiahydrosapphyrin 1 yields dimers, 2(ant)i and 2(syn), comprising a transoid-oriented plate-like bipyrrolo[1,2-a] indolylidene. The thiophene-containing tetrapyrrole arching subunits in 2 lie at the opposite (anti) and same (syn) sides of the plate, respectively. Meanwhile, multiply fused cisoid-orientated dimer 3 was also obtained; a polycyclic pyrrolo-bridged bipyrroloindole derivative tethered with fully pi-conjugated bridges was formed. Notably, the anti-dimer 2(anti) underwent subsequent oxidative fusion to furnish a further-fused [6.5.5.7.5.5.5.6]-octacyclic compound 4(anti). In contrast, the syn-orientated 2(syn) could not be further fused due to the long distance between the potential reaction sites. This study provides a unique approach to the fused dimeric porphyrin analogs for potential near-infrared optical materials by a simple oxidation reaction. It also reveals the importance of conformation-modulated reactivity for constructing complex porphyrin arrays.
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27.
  • Li, Qizhao, et al. (författare)
  • Regioselectively Halogenated Expanded Porphyrinoids as Building Blocks for Constructing Porphyrin-Porphyrinoid Heterodyads with Tunable Energy Transfer
  • 2019
  • Ingår i: Journal of the American Chemical Society. - : AMER CHEMICAL SOC. - 0002-7863 .- 1520-5126. ; 141:13, s. 5294-5302
  • Tidskriftsartikel (refereegranskat)abstract
    • Expanded porphyrins have been attracting increasing attention owing to their unique optical and electrochemical properties as well as switchable aromaticity. Toward material applications, regioselective functionalization of the expanded porphyrins at their periphery is indeed challenging due to the presence of multiple reactive sites. Herein, a set of regioselective halogenated isomers (L5-Br-A/B/C) of neo-confused isosmaragdyrin (L5) are synthesized by a combination of the halogenation reaction of L5 and sequential macrocycleto-macrocycle transformation reactions of its halogenated isomers. On this basis, the regioselectively functionalized isosmaragdyrins are utilized as building blocks for constructing multichromophoric porphyrinoids, specifically, heterodyads L5-ZnP-A/B/C, in which a common zinc porphyrin is linked at three different pyrrolic positions of isosmaragdyrins, respectively, by Sonogashira coupling reactions. The highly efficient energy cascade from porphyrin to isosmaragdyrin is elucidated using steady-state/time-resolved spectroscopies and theoretical calculations. Notably, the energy transfer processes from the porphyrin to the isosmaragdyrin moieties as well as the excitation energy transfer rates in L5-ZnP-A/B/C are highly dependent on the linking sites by through-bond and Forster-type resonance energy transfer mechanisms. The site-selective functionalization and subsequent construction of a set of heterodyads of the expanded porphyrinoid would provide opportunities for developing new materials for optoelectronic applications.
  •  
28.
  • Li, Qizhao, et al. (författare)
  • Skeletal Rearrangement of Twisted Thia-Norhexaphyrin : Multiply Annulated Polypyrrolic Aromatic Macrocycles
  • 2019
  • Ingår i: Angewandte Chemie International Edition. - : WILEY-V C H VERLAG GMBH. - 1433-7851 .- 1521-3773. ; 58:18, s. 5925-5929
  • Tidskriftsartikel (refereegranskat)abstract
    • A hybrid thia-norhexaphyrin comprising a directly linked N-confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner-annulated aromatic macrocycles. Oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone triggered a cleavage of the C-S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique pi-conjugated products: a thiopyrrolo-pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur-free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H-thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions. Using expanded porphyrin scaffolds, oxidative thiophene cleavage and desulfurization of the hitherto unknown N-confused core-modified macrocycles would be a practical approach for developing unique polypyrrolic aromatic macrocycles.
  •  
29.
  • Li, Qizhao, et al. (författare)
  • Twisted-Planar-Twisted expanded porphyrinoid dimer as a rudimentary reaction-based methanol indicator
  • 2020
  • Ingår i: Nature Communications. - : Springer Nature. - 2041-1723. ; 11:1
  • Tidskriftsartikel (refereegranskat)abstract
    • Directly linked porphyrin dimers have attracted considerable attention because of their intriguing electronic features. Most emphasis has been placed on either dimers with large dihedral angles between the constituent planar monomeric subunits or those with overall planarity, referred to as "Planar-Twisted-Planar" and "Planar-Planar-Planar", respectively. Herein, we report a "Twisted-Planar-Twisted" framework, the hexaphyrin dimer D that exists in a trans configuration. Treatment of D with MeOH affords two isomeric dimers, MD1 and MD2, both of which incorporate a methoxy moiety and exist in cis orientations with respect to the tethering linkage. The methanol-promoted conversion is accompanied by a readily discernible color change from green to brown and is not induced to an appreciable level by other alcohols. Dimer D thus acts as a rudimentary, albeit highly selective, reaction-based methanol indicator. This work provides a promising approach for constructing reaction-based chemosensors using porphyrinoid dimers of nonplanar subunits with biased reactivity. Directly linked porphyrin dimers show intriguing electronic features but emphasis has been placed on planar monomeric units. Here, the authors report a Twisted-Planar-Twisted framework which can undergo a cis-trans transformation accompanied by a colour change in presence of methanol, making this framework applicable as a methanol sensor.
  •  
30.
  • Li, Wenlong, et al. (författare)
  • Enantiospecific photoresponse of sterically hindered diarylethenes for chiroptical switches and photomemories
  • 2015
  • Ingår i: Scientific Reports. - : Springer Science and Business Media LLC. - 2045-2322. ; 5
  • Tidskriftsartikel (refereegranskat)abstract
    • Light-driven transcription, replication and enzyme catalysis are critically dependent upon a delicate transfer between molecular and supramolecular chirality. Chemists have well realized the impressive stereospecificity over many thermally accessible cycloaddition with chiral catalysts, but making light work in the enantiomer control of diarylethene photocyclization has proved to be more challenging. Here, we report a unique sterically hindered diarylethene (BBTE) system with absolute enantiospecific photocyclization and cycloreversion. Moreover, we have fully separated all the five thermally stable isomers, consisting of one achiral parallel conformer, one pair of anti-parallel ring-open enantiomers, and another pair of ring-closed enantiomers, whose absolute chiral configurations are entirely elucidated by single X-ray crystallographic analyses. The photo-responsive feature exhibits a reversible, complete enantio-control transformation without racemism, offering an unrivaled unimolecular enantiospecific platform for potential applications as bistable chiroptical switches and all-photonic photomemories with optical rotation as non-destructive readout.
  •  
31.
  • Lu, Yunyue, et al. (författare)
  • Multiply Wrapped Porphyrin Dyes with a Phenothiazine Donor : A High Efficiency of 11.7% Achieved through a Synergetic Coadsorption and Cosensitization Approach
  • 2019
  • Ingår i: ACS Applied Materials and Interfaces. - : AMER CHEMICAL SOC. - 1944-8244 .- 1944-8252. ; 11:5, s. 5046-5054
  • Tidskriftsartikel (refereegranskat)abstract
    • Photocurrent (J) and photovoltage (Vac) are two important parameters for dye-sensitized solar cells (DSSCs) to achieve high power conversion efficiencies (PCEs). Herein, we synthesize four novel porphyrin dyes, XW36 XW39, using an N-phenyl-substituted phenothiazine donor to pursue higher PCE. For XW36 and XW37, the N-phenyl group is wrapped with two ortho-alkoxy chains. In contrast, it is substituted with a para-alkoxy group in XW38 and XW39. The phenothiazine wrapping in XW36 and XW37 induces more serious distortion, which is beneficial for anti-aggregation but unfavorable for the electron transfer from donor to a porphyrin framework. Thus, individual porphyrin dyes XW36 and XW37 exhibit efficiencies of 9.05 and 9.58%, respectively, lower than those of 9.51 and 10.0% achieved for XW38 and XW39, respectively. Besides, the introduction of a methyl group into a benzoic acid acceptor unit is conducive to anti-aggregation and thus improves the V-oc and efficiencies. Therefore, higher efficiencies were achieved for XW37 and XW39, compared with XW36 and XW38, respectively. Interestingly, although the individual XW36 dye shows a lowest efficiency among the four dyes, a highest efficiency of 11.7% was obtained for XW36 on the basis of synergetic adsorption with chenodeoxycholic acid and PT-C6 because of simultaneously improved J and Voc, which may be ascribed to the lowest dye-loading amount of XW36 among all of these porphyrin dyes, with the largest vacancy area left on the TiO2 surface available for cosensitizer PT-C6, resulting in a highest J. The high efficiency of 11.7% is one of the highest efficiencies using I-/I-3(-) electrolytes in DSSCs. These results provide an effective strategy for developing efficient DSSCs by the targeted coadsorption and cosensitization of porphyrin sensitizers optimized through introducing a bis(ortho-alkoxy)-wrapped phenyl group into the phenothiazine donor and/or methyl groups into the benzoic acid acceptor unit.
  •  
32.
  • Luo, Jiaxin, et al. (författare)
  • Solar cells sensitized by donor-linked concerted companion dyes
  • 2023
  • Ingår i: Journal of Materials Chemistry C. - : ROYAL SOC CHEMISTRY. - 2050-7526 .- 2050-7534. ; 11:16, s. 5450-5460
  • Tidskriftsartikel (refereegranskat)abstract
    • Recently, concerted companion (CC) dyes have been developed by covalently linking the acceptors of organic and porphyrin dye units. Herein, a new class of CC dyes XW85 and XW86 have been designed by linking the donors of porphyrin and organic dye units with C6H12 and C12H24 chains, respectively. The DSSCs of XW85 based on the I-3(-)/I- electrolyte show significant J(SC) (17.20 mA cm(-2)) and PCE (8.96%), and XW86 exhibits higher J(SC) (18.55 mA cm(-2)) and PCE (9.76%), which are also higher than those of the corresponding cosensitization systems. However, the PCEs for XW85 and XW86 are lower than that of the acceptor-linked reference dye XW76 despite the obviously larger dye adsorption amounts. Desorption studies reveal that the CC dyes may be either double-anchored or single-anchored, with the double/single anchoring ratios lying in a sequence of XW85 (1.31) < XW86 (1.88) < XW76 (6.34), consistent with that of increasing PCE. These observations indicate that the non-adsorbed sub-dye unit cannot effectively contribute to electron injection, and thus relatively large mono-anchoring proportions for XW85 and XW86 result in their relatively low J(SC), and the difference between XW85 and XW86 indicates that a longer linking chain is beneficial for partially alleviating the unfavorable single anchoring, resulting in superior performance. The results indicate that the photovoltaic behavior for the CC dyes may be further enhanced by avoiding the unfavorable alignment of the two carboxyl groups in opposite directions and thus simultaneously anchoring the two carboxyl groups, which may be realized through more rational molecular design.
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33.
  • Song, Heli, et al. (författare)
  • Branched and linear alkoxy chains-wrapped push-pull porphyrins for developing efficient dye-sensitized solar cells
  • 2017
  • Ingår i: Dyes and pigments. - : Elsevier BV. - 0143-7208 .- 1873-3743. ; 137, s. 421-429
  • Tidskriftsartikel (refereegranskat)abstract
    • Four alkoxy-wrapped push-pull porphyrin dyes containing the phenothiazine derived donor and the ethynylbenzoic acid acceptor have been designed, synthesized and used as sensitizers for fabricating efficient dye-sensitized solar cells (DSSCs). Branched or linear alkoxy chains were introduced to the ortho-positions of the meso-phenyl moieties to suppress the dye aggregation and charge recombination. The effect of alkoxy chains were investigated in the absence and presence of an additional electron withdrawing benzothiadiazole unit. In the former cases, almost identical photovoltaic efficiencies of similar to 8.3% were achieved for both the branched and the linear alkoxy chains, while in the latter cases, the planar benzothiadiazole unit induces serious dye aggregation and charge recombination, resulting in lower efficiencies of 6.46% and 7.50% for the linear and branched chains, respectively, even though broader absorption was achieved. The relatively higher efficiency achieved for the dyes with branched chains may be related to the better effect of suppressing the dye aggregation and charge recombination. Furthermore, the coadsorption approach was employed, and a highest efficiency of 9.62% was achieved for the dye that features branched chains and the benzothiadiazole unit. These results compose a novel approach for developing efficient DSSCs by combining the coadsorbent with a porphyrin dye containing both the additional benzothiadiazole acceptor and branched alkoxy chains.
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34.
  • Sun, Meng, et al. (författare)
  • Mono- and bis-Pd(II) complexes of N-confused dithiahexaphyrin(1.1.1.1.1.0) with the absorption and aromaticity modulated by Pd(II) coordination, macrocycle contraction and ancillary ligands
  • 2024
  • Ingår i: Chemical Science. - : ROYAL SOC CHEMISTRY. - 2041-6520 .- 2041-6539.
  • Tidskriftsartikel (refereegranskat)abstract
    • To further enrich the coordination chemistry of hexaphyrins and probe the underlying property-structural correlations, N-confused dithiahexaphyrin(1.1.1.1.1.0) (1) with 26 pi-electron H & uuml;ckel aromaticity was synthesized. Based on its unprecedented two unsymmetrical cavities, five palladium complexes 2, 3, 4-Ph, 4-Cl and 5 have been successfully synthesized under various coordinations. Thus, two mono-Pd(II) complexes 2 and 3 with the Pd(II) atom coordinated in the two different cavities were obtained by treating 1 with palladium reagents PdCl2, and (PPh3)(2)PdCl2 respectively. On this basis, bis-Pd(II) complexes 4-Ph and 4-Cl were synthesized by treating 2 and 3 with (PPh3)(2)PdCl2 and PdCl2, respectively. As a result, both 4-Ph and 4-Cl contain two Pd(II) atoms coordinated within the two cavities, with one of the Pd(II) atoms further coordinated to a triphenylphosphine ligand in addition to an anionic ancillary ligand of Ph- and Cl-, respectively. Notably, a further contracted mono-Pd(II) complex 5 was synthesized by treating 1 with Pd(PPh3)(4) by eliminating one of the meso-carbon atoms together with the corresponding C6F5 moiety. These complexes present tunable 26 pi aromaticity and NIR absorption up to 1060 nm. This work provides an effective approach for developing distinctive porphyrinoid Pd(II) complexes from a single porphyrinoid, without resorting to tedious syntheses of a series of porphyrinoid ligands.
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35.
  •  
36.
  • Tang, Yunyu, et al. (författare)
  • Porphyrins Containing a Triphenylamine Donor and up to Eight Alkoxy Chains for Dye-Sensitized Solar Cells : A High Efficiency of 10.9%
  • 2015
  • Ingår i: ACS Applied Materials and Interfaces. - : American Chemical Society (ACS). - 1944-8244 .- 1944-8252. ; 7:50, s. 27976-27985
  • Tidskriftsartikel (refereegranskat)abstract
    • Porphyrins are promising DSSC sensitizers due to their structural similarity to chlorophylls as well as their tunable strong absorption. Herein, a novel D-pi-A porphyrin dye XW14 containing a strongly electron-donating triphenyl-amine moiety as the electron donor was designed and synthesized: To avoid undesirably decreased V-oc caused by dye aggregation effect, two methoxy or hexyloxy chains were introduced to the para positions of the triphenylamine moiety to afford XW15 and XW16, respectively. To further extend the absorption to a longer wavelength, a benzothiadiazole unit was introduced as an auxiliary acceptor to furnish XW17. Compared with XW14, the introduction of additional methoxy or hexyloxy groups in XW15 and XW16 red-shift the onset wavelengths from 760 to 780 and 790 nm, respectively. More impressively, XW17 has a more extended pi-conjugation framework, and thus, it exhibits a much broader IPCE spectrum with an extremely red-shifted onset wavelength Of 830 mu, resulting in the highest J(sc) (18.79 mA cm(-2)). On the other hand, the hexyloxy chains are favorable for suppressing the dye aggregation effect, and thus XW16 shows the highest V-oc 734 mV. As a result, XW16 and XW17 demonstrate photovoltaic efficiencies of 9,1 and 9.5%, respectively, higher than those of XW14 (8.6%) and XW15 (8.7%), and obviously higher than that of 7.94% for our previously reported dye, XW4. On the basis of optimized porphyrin dye XW17, we used a nonporphyrin dye with a high V-oc and strong absorption around 500 inn (WS-5) as the cosensitizer to improve the V-oc from 700 to 748 mV, with synergistical J(sc) enhancement from 18.79 to 20.30 mA cm(-2). Thus, the efficiency was dramatically enhanced to 10.9%, which is among the highest efficiencies obtained for the DSSCs based on traditional iodine electrolyte. In addition, the DSSCs based on XW17 + WS-5 exhibit good photostability, which is beneficial for practical applications.
  •  
37.
  • Tang, Yunyu, et al. (författare)
  • Solar cells sensitized with porphyrin dyes with a carbazole donor : The effects of an auxiliary benzothiadiazole acceptor and bulky substituents on the donor
  • 2019
  • Ingår i: Dyes and pigments. - : ELSEVIER SCI LTD. - 0143-7208 .- 1873-3743. ; 171
  • Tidskriftsartikel (refereegranskat)abstract
    • Three porphyrin sensitizers XW54-XW56 containing a carbazole donor have been designed and synthesized by introducing a benzothiadiazole (BTD) unit as the auxiliary electron acceptor to extend the absorption spectra and/or bulky dihexyloxyphenyl groups into the carbazole unit to suppress dye aggregation and improve the photovoltage (V-OC). The BTD unit incorporated in XW54 obviously broadens and red-shifts the absorption threshold to ca. 700 nm, as compared with that of 650 nm observed for XW1. Thus, XW54 exhibits a much broader monochromatic photon-to-electron conversion efficiency (IPCE) spectrum with an extremely red-shifted onset wavelength of 780 nm, resulting in a photocurrent density (J(SC)) of 11.60 mA cm(-2), higher than that of XW1. Unfortunately, the V-OC value was decreased owing to the more severe dye aggregation caused by the large conjugation framework induced by the presence of the BTD unit. As a result, XW54 shows an efficiency of 6.26%, slightly higher than that of 6.11% obtained for XW1. On the other hand, with the bulky dihexyloxyphenyl donor groups introduced to XW55, a highest V-OC, of 860 mV was achieved, which can be ascribed to the efficient prevention of charge recombination and suppression of dye aggregation. Thus, XW55-based cells exhibit an improved efficiency of 6.60%. On the basis of XW54 and XW55, two bulky dihexyloxyphenyl groups and a BTD unit were simultaneously introduced to XW56, affording a highest efficiency of 7.03%, with the J(SC )and V-OC, values of 12.5 mA cm(-2) and 785 mV, respectively. These results compose a novel approach for developing efficient dye-sensitized solar cells (DSSCs) by simultaneously introducing bulky dihexyloxyphenyl groups and a benzothiadiazole unit, which may synergistically broaden the absorption spectra and suppress the dye aggregation, resulting in improved photocurrent and photovoltage.
  •  
38.
  • Wang, Yueqiang, et al. (författare)
  • 2-Diphenylaminothiophene as the donor of porphyrin sensitizers for dye-sensitized solar cells
  • 2014
  • Ingår i: New Journal of Chemistry. - : Royal Society of Chemistry (RSC). - 1144-0546 .- 1369-9261. ; 38:7, s. 3227-3235
  • Tidskriftsartikel (refereegranskat)abstract
    • Four novel D-pi-A porphyrin dyes (YQ1 YQ4) with 2-diphenylaminothiophene attached at the mesoposition as the electron donor have been synthesized and used as the sensitizers for dye sensitized solar cells (DSSCs). 4-Ethynylbenzoic acid and 2-cyanoacrylic acid were incorporated as the anchoring moieties in YQ1, and YQ2 YQ4, respectively. Due to the extended conjugation size, the absorption spectra of YQ2 YQ4 showed Soret band maxima in the range of 447-468 nm, which is red shifted as compared to that of 446 nm for Y01. Furthermore, in comparison with most reported porphyrin dyes with similar structures, YQ1-YQ4 demonstrate obviously red-shifted absorption maxima and broadened Soret bands, indicating that these porphyrin dyes may be developed as promising DSSC sensitizers. The electrochemical studies and DFT calculations indicated that all the four dyes were capable of serving as DSSC sensitizers. Thus, DSSCs were fabricated based on these dyes. The cells based on YQ4 showed the power conversion efficiency of 5.00%, which is higher than those of 4.23% and 4.38% for YQ2 and YQ3, respectively. This observation may be attributed to the suppression of the dye aggregation by the hexyl group attached to the thienyl ring of YQ4. On the other hand, YQ2 YQ4 demonstrated lower efficiencies compared with Y01, which may be ascribed to the floppy structures of the cyanoacrylic acid-based porphyrins that provide free space for charge recombination. As a result, the DSSCs based on Y01 exhibited the highest efficiency of 6.01%. This work demonstrates that the introduction of 2-diphenylaminothiophene into a porphyrin framework can obviously red-shift and broaden the absorption bands of the porphyrin dyes, resulting in high solar cell efficiencies. Hence, the introduction of 2-diphenylaminothiophene as the electron donor may be promising for the design of efficient porphyrin-based DSSC sensitizers.
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39.
  • Wang, Yueqiang, et al. (författare)
  • Porphyrins bearing long alkoxyl chains and carbazole for dye-sensitized solar cells : tuning cell performance through an ethynylene bridge
  • 2013
  • Ingår i: RSC Advances. - : Royal Society of Chemistry (RSC). - 2046-2069. ; 3:34, s. 14780-14790
  • Tidskriftsartikel (refereegranskat)abstract
    • Two novel porphyrin dyes (Q1 and Q2) bearing alkoxyl chains with a carbazole moiety as the electron donor have been synthesized and utilized as sensitizers for dye-sensitized solar cells (DSSCs). Compared with Q2, the molecule of Q1 has an additional ethynylene bridge between the carbazole moiety and the porphyrin framework. Photophysical and electrochemical properties of the two dyes were investigated by UV-vis, fluorescence spectroscopy and cyclic voltammetry. DFT calculations indicated that Q2 has a more twisted non-planar conformation associated with a smaller p conjugation size because of the absence of ethynylene bridge, which resulted in its better solubility and larger amount of adsorption on TiO2. Compared with Q1, Q2 showed better photovoltaic performance, with a short-circuit photocurrent density (J(sc)) of 11.3 mA cm(-2), an open-circuit photovoltage (V-oc) of 0.68 V, and a fill factor (ff) of 0.71, corresponding to an overall conversion efficiency of 5.51% under standard global AM 1.5 solar light conditions. The additional ethynylene bridge in Q1 extends the absorption bands to a longer wavelength region with the absorption threshold of 743 nm on the TiO2 film compared with that of 681 nm for Q2, but the cell efficiency is decreased to 2.22%, which may be ascribed to the worse solubility and stronger aggregation tendency resulting from the better molecule planarity. These results indicate that the extension of the absorption bands to a longer wavelength region by the introduction of an additional ethynylene bridge may result in worse solubility and more severe aggregation, and thus decrease the cell efficiency. For the design of efficient DSSC sensitizers, these contradictory effects must be fully considered and well balanced.
  •  
40.
  • Wei, Pingchun, et al. (författare)
  • Neo-Fused Hexaphyrin : A Molecular Puzzle Containing an N-Linked Pentaphyrin
  • 2014
  • Ingår i: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 53:51, s. 14069-14073
  • Tidskriftsartikel (refereegranskat)abstract
    • The first neo-confused hexaphyrin(1.1.1.1.1.0) was synthesized by oxidative ring closure of a hexapyrrane bearing two terminal "confused" pyrroles. The new compound displays a folded conformation with a short interpyrrolic C center dot center dot center dot N distance of 3.102 angstrom, and thus it readily underwent ring fusion to afford a neo-fused hexaphyrin with an unprecedented 5,5,5,7-tetracyclic ring structure. Furthermore, coordination of Cu-II triggered a ring opening/contracting reaction to afford a Cu-II complex of an N-linked pentaphyrin derivative. The roles of reactive N-C bonds in the porphyrinoid macrocycles were demonstrated.
  •  
41.
  • Wei, Tiantian, et al. (författare)
  • Systematic Investigations on the Roles of the Electron Acceptor and Neighboring Ethynylene Moiety in Porphyrins for Dye-Sensitized Solar Cells
  • 2015
  • Ingår i: ACS Applied Materials and Interfaces. - : American Chemical Society (ACS). - 1944-8244 .- 1944-8252. ; 7:39, s. 21956-21965
  • Tidskriftsartikel (refereegranskat)abstract
    • Cyanoacrylic and carboxyl groups have been developed as the most extensively used electron acceptor and anchoring group for the design of sensitizers for dye-sensitized solar cells. In terms of the photoelectric conversion efficiency, each of them has been demonstrated to be superior to the other one in certain cases. Herein, to further understand the effect of these two groups on cell efficiencies, a series of porphyrin sensitizers were designed and synthesized, with the acceptors systematically varied, and the effect of the neighboring ethynylene unit was also investigated. Compared with the sensitizer XW5 which contains a carboxyphenyl anchoring moiety directly linked to the meso-position of the porphyrin framework, the separate introduction of a strongly electron-withdrawing cyanoacrylic acid as the anchoring group or the insertion of an ethynylene unit can achieve broadened light absorption and IPCE response, resulting in higher J(sc) and higher efficiency. Thus, compared with the efficiency of 4.77% for XW5, dyes XW1 and XW6 exhibit higher efficiencies of 7.09% and 5.92%, respectively. Simultaneous introduction of the cyanoacrylic acid and the ethynylene units into XW7 can further broaden light absorption and thus further improve the J(sc). However, XW7 exhibits the lowest V-oc value, which is not only related to the floppy structure of the cyanoacrylic group but also related to the aggravated dye aggregation effect due to the extended framework. As a result, XW7 exhibits a relatively low efficiency of 5.75%. These results indicate that the combination of the ethynylene and cyanoacrylic groups is an unsuccessful approach. To address this problem, a cyano substituent was introduced to XW8 at the ortho position of the carboxyl group in the carboxyphenyl acceptor. Thus, XW8 exhibits the highest efficiency of 7.59% among these dyes. Further cosensitization of XW8 with XS3 dramatically improved the efficiency to 9.31%.
  •  
42.
  • Xie, Yongshu, et al. (författare)
  • Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer
  • 2013
  • Ingår i: Journal of the American Chemical Society. - : American Chemical Society (ACS). - 0002-7863 .- 1520-5126. ; 135:51, s. 19119-19122
  • Tidskriftsartikel (refereegranskat)abstract
    • Cyclization of a pentapyrrane with two terminal beta-linked pyrroles afforded a dihydrosapphyrin isomer (1) with the pyrroles linked in a unique beta,alpha-alpha,beta mode, which was rather reactive, and thus it readily underwent a ring-contracted rearrangement to a pyrrolyl norrole (2), and succeeding ring expansion to a terpyrrole-containing isosmaragdyrin analogue (4). 1, 2, and 4 contain the internal ring pathways with a minimum of 17, 15, and 16 atoms, respectively. 1, 2, and 4 are almost nonfluorescent, whereas the complex of 2 with Zn2+ shows a distinct NIR emission peak at 741 nm. The unprecedented pyrrole transformation chemistry by confusion approach is illustrated.
  •  
43.
  • Xu, Yue, et al. (författare)
  • Confusion Approach Modulated Syntheses of Corrorin Parasitized Hexaphyrins(1.1.1.1.1.0) and the Oxidative Ring Cleavage Behavior
  • 2021
  • Ingår i: Organic Letters. - : AMER CHEMICAL SOC. - 1523-7060 .- 1523-7052. ; 23:21, s. 8307-8311
  • Tidskriftsartikel (refereegranskat)abstract
    • A corrorin parasitized hexaphyrin(1.1.1.1.1.0) 1 was synthesized by [4 + 4] condensation, and subsequent treatment with PbO2 afforded hexaphyrin 2 appended with a dipyrrinone moiety via regioselective opening of the corrorin ring. In contrast, oxidation of the corresponding corrorin-N-confused hexaphyrin(1.1.1.1.1.0) hybrid 3 afforded only a keto adduct 4. As a result, the planarity and aromaticity of the hexaphyrin moiety can be modulated.
  •  
44.
  • Xu, Yue, et al. (författare)
  • Pyrrolylmethylene Appended Corrorin: Peripheral Coordination and Transformation to Pyridyl Incorporated Hemiporphycene Analogue
  • 2023
  • Ingår i: Organic Letters. - : AMER CHEMICAL SOC. - 1523-7060 .- 1523-7052. ; 25:10, s. 1793-1798
  • Tidskriftsartikel (refereegranskat)abstract
    • A pyrrolylmethylene appended corrorin 1 was synthesized and coordinated with [Rh(CO)2Cl]2 to afford 1-Rh with unique RhI-eta 2-CC bonding in addition to the coordination of the dipyrrin-like unit and a carbonyl ligand. Further oxidation of 1 afforded 2, exhibiting a hydrocorrorinone core, and it can be further transformed into pyrrolo[3,2c]pyridine incorporated hemiporphycene analogue 3 upon treatment with HOAc. The side chain modifies the reactivity of corrorin and effectively tunes the NIR absorption of the resulting porphyrinoids.
  •  
45.
  • Xu, Yue, et al. (författare)
  • Syntheses of Thiophene-Thiophene-Linked Corrorin Dimers with Tunable Near-Infrared Absorption and Distinctive Reactivity
  • 2024
  • Ingår i: Organic Letters. - : AMER CHEMICAL SOC. - 1523-7060 .- 1523-7052. ; 26:2, s. 571-576
  • Tidskriftsartikel (refereegranskat)abstract
    • Thiahexaphyrinone 1 and thia-dipyrrin-appended corrorin 2 have been synthesized. Surprisingly, further oxidation of compound 2 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dichloromethane afforded dimer 3 with two molecules of compound 2 linked at the alpha-carbon atoms of the thienyl units. Treatment of compound 3 with DDQ in MeOH and SnCl2 in tetrahydrofuran/H2O afforded the dimethoxy-attached dimer 4 and hydrogenated dihydroxy-attached dimer 5, respectively. These results provide the first examples for synthesizing thiophene-linked porphyrinoid dimers with tunable near-infrared absorption and chirality.
  •  
46.
  • Yang, Guosheng, et al. (författare)
  • Efficient Solar Cells Based on Porphyrin Dyes with Flexible Chains Attached to the Auxiliary Benzothiadiazole Acceptor : Suppression of Dye Aggregation and the Effect of Distortion
  • 2017
  • Ingår i: ACS Applied Materials and Interfaces. - : AMER CHEMICAL SOC. - 1944-8244 .- 1944-8252. ; 9:42, s. 36875-36885
  • Tidskriftsartikel (refereegranskat)abstract
    • Donor-pi-acceptor-type porphyrin dyes have been widely used for the fabrication of efficient dye-sensitized solar cells (DSSCs) owing to their strong absorption in the visible region and the ease of modifying their chemical structures and photovoltaic behavior. On the basis of our previously reported efficient porphyrin dye XW11, which contains a phenothiazine-based electron donor, a pi-extending ethynylene unit, and an auxiliary benzothiadiazole acceptor, we herein report the syntheses of novel porphyrin dyes XW26- XW28 by introducing one or two alkyl/alkoxy chains into the auxiliary acceptor. The introduced chains can effectively suppress dye aggregation. As a result, XW26 XW28 show excellent photovoltages of 700, 701, and 711 mV, respectively, obviously higher than 645 mV obtained for XW11. Nevertheless, the optimized structures of XW26 and XW27 exhibit severe distortion, showing large dihedral angles of 57.2(circle) and 44.0(circle), respectively, between the benzothiadiazole and benzoic acid units, resulting from the steric hindrance between the benzoic acid unit and the neighboring alkyl/alkoxy chain on the benzothiadiazole unit, and thus blue-shifted absorption, decreased photocurrents. and low efficiencies of 5.19% and 6.42% were observed for XW26 and XW27, respectively. Interestingly, XW26 exhibits a more blue -shifted absorption spectrum relative to XW27, indicating that the steric hindrance of the alkyl/alkoxy chains has a more pronounced effect than the electronic effect. Different from XW26 and XW27, XW28 contains only one alkyl chain neighboring the ethynylene unit, which does not induce obvious steric hindrance with the benzoic acid unit, and thus distortion of the molecule is not seriously aggravated compared with XW11. Hence, its absorption spectrum and photocurrent are similar to those of XW11. As a result, a higher efficiency of 9.12% was achieved for XW28 because of its suppressed dye aggregation and higher photovoltage. It is worth noting that a high efficiency of 10.14% was successfully achieved for XW28 upon coadsorption with CD CA, which is also higher than the corresponding efficiency obtained for XW11. These results provide a novel approach for developing efficient porphyrin dyes by introducing chains into the suitable position of the auxiliary benzothiadiazolyl moiety to suppress dye aggregation, without seriously aggravating distortion of the dye molecules.
  •  
47.
  • Yang, Zhen, et al. (författare)
  • Synthesis and coordination of a dipyrrin appended N-confused porphyrin
  • 2023
  • Ingår i: Journal of Porphyrins and Phthalocyanines. - : World Scientific. - 1088-4246 .- 1099-1409. ; 27:1, s. 285-292
  • Tidskriftsartikel (refereegranskat)abstract
    • A hexapyrrane P6 with a terminal N-confused pyrrole was synthesized by acid-catalyzed [3+3] condensation followed by oxidation with DDQ, which did not afford the expected N-confused hexaphyrin. In stead, a rearranged product, i.e., α-dipyrrin appended N-confused porphyrin 1 was obtained in a yield of 46%. Chelation of 1 with Pt(II) afforded the peripheral complex 1-Pt, which was further coordinated with Rh(I) in the cavity to afford the corresponding bimetallic complex 1-Pt-Rh. Both 1-Pt and 1-Pt-Rh exhibit split Soret-like bands and noticeable Q-like bands tailing to the NIR region up to ca. 1200 nm. Single crystal X-ray diffraction analyses of 1 and 1-Pt revealed that the peripheral coordination of Pt(II) slightly modifies the interplanar angle between the porphyrin macrocycle and the dipyrrin unit, which may modulate the absorption spectra. The results of this work compose an interesting example of synthesizing porphyrinoids appended with conjugated peripheral chains by the oxidative ring closure reaction of an oligopyrrane containing a terminal N-confused pyrrole, and such compounds may be used for both inner and peripheral coordination to afford complexes with tunable NIR absorption.
  •  
48.
  • Zhang, Kai, et al. (författare)
  • Oxidative Ring Closure and Metal Triggered Ring Opening : Syntheses of Macrocyclic and Linear Hexapyrroles
  • 2014
  • Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 16:24, s. 6354-6357
  • Tidskriftsartikel (refereegranskat)abstract
    • A C6F5-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorindipyrrin conjugate (2), and subsequent FeCl3-assisted oxidative cleavage of 2 afforded a terminally di-a-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl3 afforded 3, a hexapyrrinone Fe3+ complex (4), and a hexaphyrin (1,1,1,1,1,0) (5). These results indicate that the oxidation of hexapyrranes may be developed as an effective approach for the syntheses of novel linear and macrocyclic hexapyrroles.
  •  
49.
  • Zhang, Kai, et al. (författare)
  • Synthesis of a Neo-Confused Octaphyrin and the Formation of Its Mononuclear Complexes
  • 2015
  • Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 17:19, s. 4806-4809
  • Tidskriftsartikel (refereegranskat)abstract
    • Novel neo-confused octaphyrin(1.1.1.1.1.1.1.0) (1) was synthesized by oxidative ring closure of an octapyrrane bearing two terminal "confused" pyrroles. Crystal structures of its Zn(II) and Cu(II) complexes (2 and 3) show a figure-of-eight conformation with unique mononuclear coordination structures. Photophysical data and theoretical calculations suggest that the neo-confused octaphyrin 1 is a 34 pi electron conjugated species showing nonaromaticity. Coordination of pocopper and zinc ions results in the further narrowing of the HOMO-LUMO gaps.
  •  
50.
  • Zou, Jiazhi, et al. (författare)
  • Efficient Dye-Sensitized Solar Cells Based on a New Class of Doubly Concerted Companion Dyes
  • 2022
  • Ingår i: ACS Applied Materials and Interfaces. - : American Chemical Society (ACS). - 1944-8244 .- 1944-8252. ; 14:29, s. 33274-33284
  • Tidskriftsartikel (refereegranskat)abstract
    • To develop efficient dye-sensitized solar cells (DSSCs), concerted companion (CC) dyes XW60-XW63 constructed from the covalent linkage of a strapped porphyrin dye unit and an organic dye unit have been reported to exhibit panchromatic absorption and excellent photovoltaic performance. However, these CC dyes only afforded moderate V-OC values of ca. 763 mV, demonstrating relatively weak antiaggregation ability, which remains an obstacle for further enhancing the photovoltaic behavior. To address this problem, we herein develop porphyrin dyes XW77-XW80 with the macrocycles wrapped with alkoxy chains of various lengths (OC6H13-OC22H45) and the corresponding CC dyes XW81-XW84 containing these porphyrin dye units. Interestingly, the new CC dyes XW81-XW83 exhibit increasing V-OC from 745 to 784 mV with the chain lengths extended from C6 to C18, and a lowered V-OC of 762 mV was obtained for XW84 when the chain length was further extended to C22. As a result, XW83 afforded the highest PCE of 12.2%, which is, to the best of our knowledge, the record efficiency for the iodine electrolyte-based solar cells sensitized with a single dye. These results can be rationalized by the so-called doubly concerted companion (DCC) effects, that is, the two subdye units exhibit not only complementary absorption but also concerted antiaggregation with the long wrapping chains on the porphyrins unit simultaneously protecting the porphyrin macrocycle and the neighboring organic subdye unit, thus affording panchromatic absorption and strong antiaggregation and anticharge-recombination ability. These results provide a new approach for constructing a class of DCC dyes to achieve high-performance DSSCs without using any antiaggregating coadsorbent or absorption-enhancing cosensitizer.
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