| 1. |
- Chen, Bin, et al.
(författare)
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A novel trigeminal zinc porphyrin and corresponding porphyrin monomers for dye-sensitized solar cells
- 2014
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Ingår i: RSC Advances. - : Royal Society of Chemistry (RSC). - 2046-2069. ; 4:21, s. 10439-10449
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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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| 2. |
- Chen, Bin, et al.
(författare)
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Full-colour luminescent compounds based on anthracene and 2,2 '-dipyridylamine
- 2013
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Ingår i: Journal of Materials Chemistry C. - : Royal Society of Chemistry (RSC). - 2050-7526 .- 2050-7534. ; 1:44, s. 7409-7417
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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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| 3. |
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| 4. |
- Chen, Bin, et al.
(författare)
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TICT based fluorescence "turn-on" hydrazine probes
- 2014
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Ingår i: Sensors and actuators. B, Chemical. - : Elsevier BV. - 0925-4005 .- 1873-3077. ; 199, s. 93-100
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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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| 5. |
- Ding, Yubin, et al.
(författare)
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Acid/Base Switching of the Tautomerism and Conformation of a Dioxoporphyrin for Integrated Binary Subtraction
- 2014
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Ingår i: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 20:40, s. 12910-12916
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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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| 6. |
- Ding, Yubin, et al.
(författare)
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alpha-Monoacylated and alpha,alpha '- and alpha,beta '-Diacylated Dipyrrins as Highly Sensitive Fluorescence "Turn-on" Zn2+ Probes
- 2013
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 78:11, s. 5328-5338
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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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| 7. |
- Ding, Yubin, et al.
(författare)
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From nonconjugation to conjugation : novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes
- 2013
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Ingår i: Organic and biomolecular chemistry. - : Royal Society of Chemistry (RSC). - 1477-0520 .- 1477-0539. ; 11:16, s. 2685-2692
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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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| 8. |
- Hong, Tao, et al.
(författare)
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Syntheses of mono- and diacylated bipyrroles with rich substitution modes and development of a prodigiosin derivative as a fluorescent Zn(II) probe
- 2014
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Ingår i: RSC Advances. - : Royal Society of Chemistry (RSC). - 2046-2069. ; 4:12, s. 6133-6140
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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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| 9. |
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| 10. |
- Wang, Yueqiang, et al.
(författare)
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2-Diphenylaminothiophene as the donor of porphyrin sensitizers for dye-sensitized solar cells
- 2014
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Ingår i: New Journal of Chemistry. - : Royal Society of Chemistry (RSC). - 1144-0546 .- 1369-9261. ; 38:7, s. 3227-3235
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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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