| 1. |
- Andreasson, Joakim, 1973, et al.
(författare)
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A dihydroindolizine-porphyrin dyad as molecule-based all-photonic AND and NAND gates
- 2011
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Ingår i: Dyes and Pigments. - : Elsevier BV. - 0143-7208 .- 1873-3743. ; 89:3, s. 284-289
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Tidskriftsartikel (refereegranskat)abstract
- A molecular dyad consisting of a photochromic dihydroindolizine unit covalently linked to a porphyrin performs, when illuminated through a third-harmonic-generating crystal, the functions of both an AND and a NAND Boolean logic gate with shared all-optical inputs. The NAND gate is of particular interest as it is a so-called universal gate, and hence all other digital systems can be implemented by combinations of NAND gates. The functions of the AND and the NAND gates rely on changes in absorption and emission of the dyad in the visible spectral region upon isomerization of the photochromic unit. The change in absorption which forms the basis for the AND gate function is ascribed to the colorization/decolorization of the photochrome itself in response to the optical inputs. The variation in emission intensity which constitutes the NAND gate function is a result of the changes in redox properties of the photochrome that follow upon isomerization, such that only one of the two isomers is competent to quench the porphyrin emission by electron transfer.
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| 2. |
- Baryshnikov, Gleb V., et al.
(författare)
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Optical tuning of tetrabenzo[8]circulene derivatives through pseudorotational conformational isomerization
- 2018
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Ingår i: Dyes and pigments. - : Elsevier. - 0143-7208 .- 1873-3743. ; 151, s. 372-379
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Tidskriftsartikel (refereegranskat)abstract
- In order to further search efficient [8]circulene materials for OLED applications we have theoretically investigated the structure and electronic, absorption spectra of functionalized tetrabenzo[8]circulenes with different substituents in the outer perimeter. These hydrocarbon materials complement the wide family of [8]circulenes which earlier have been demonstrated to possess promising emissive and exciplex-forming properties suitable for organic light emitting diodes. The hydrocarbon tetrabenzo[8]circulenes show saddle shape of the molecular skeleton which can exist in two different conformations with different curvatures of the macrocycle. The aromaticity, electronic structure and orbital pattern are found to be principally different for these two isomers, where the global minimum isomer is weakly antiaromatic and electronically less stable comparing with the non-aromatic local minimum structure. The absorption spectra are also very different: the global minimum structure is more active in the long-wavelength region while the local minimum isomer shows absorption only at short wavelengths. Our computational findings suggest a new concept for optical tuning of curved [8]circulenes through conformational isomerization and aromaticity control, thus through structural variations without changing the molecular composition. Based on this principle we have designed novel functionalized [8]circulenes with promising fluorescence activity.
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| 3. |
- Bu, L., et al.
(författare)
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An AIE and ICT based NIR florescent probe for cysteine and homocysteine
- 2017
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Ingår i: Dyes and pigments. - : Elsevier BV. - 0143-7208 .- 1873-3743. ; 136, s. 724-731
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Tidskriftsartikel (refereegranskat)abstract
- A combination of aggregation-induced emission and intramolecular charge transfer was achieved by using a triphenylamine analogue and a dicyanovinyl moiety as the electron donating and accepting units, respectively. Hence, we designed and synthesized a probe with a D-π-A framework as a near-infrared fluorescence turn-on probe for biothiols (cysteine and homocysteine). Owing to the remarkable intramolecular charge transfer effect as well as intramolecular rotations associated with the donor moiety, the probe exhibits extremely weak fluorescence, which becomes a good starting point for developing fluorescence “turn-on” probes. Upon reaction with cysteine or homocysteine utilizing the dicyanovinyl moiety, the intramolecular charge transfer character was weakened, and the reacting products were observed to aggregate in aqueous solutions, resulting in the aggregation-induced emission effect with red fluorescence at 651 and 656 nm, respectively. Hence, the probe could be used as a fluorescence “turn-on” sensor for cysteine and homocysteine, with the sensing time of less than 4 min and the detection limits of 8.4 μM and 5.7 μM towards cysteine and homocysteine, respectively. The probe could distinguish cysteine and homocysteine from glutathione. The sensing mechanism was systematically investigated by employing high resolution mass spectrometry, 1H NMR and density functional theory calculations as well as checking the solvent viscosity dependent fluorescence, and thus the nucleophilic addition products, the intramolecular charge transfer character, and the aggregation-induced emission behaviour were clearly elucidated. It is noteworthy that the low cytotoxicity, the intrinsic aggregation-induced emission nature and near-infrared emissions enable the application of the probe in living cell imaging.
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| 4. |
- Carmo, C., et al.
(författare)
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Exploring the impact of meso-position fluorination on BODIPYs : Synthesis, electrochemical Insights, and potential therapeutic applications in breast cancer
- 2024
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Ingår i: Dyes and pigments. - : Elsevier BV. - 0143-7208 .- 1873-3743. ; 229
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Tidskriftsartikel (refereegranskat)abstract
- Three boron dipyrromethane molecules (BODIPYs) were synthesized in this study with different quantities of fluorine in the meso position. The samples were characterized by NMR spectroscopy, absorption, mass spectrometry, and cyclic voltammetry, which was utilized to electrochemically measure the energy gaps between the HOMO (highest-energy occupied molecular orbital) and LUMO (lowest-energy unoccupied molecular orbital). The MTT and SRB assays were used to assess the viability of these dyes in breast cancer cells (MCF-7 and HCC-1806) and African green monkey kidney cells (Vero). The newly synthesized BODIPY tris(perfluorophenoxy)phenyl (1) compound has exhibited remarkable stability and lacks photocytotoxicity in this investigation, thus rendering it a promising candidate for application in bioimaging. At defined concentrations, the BODIPYs bearing perfluorophenyl (2) and hydroxyphenyl (3) moieties have been identified as prospective candidates for photosensitization in photodynamic therapy for breast cancer. Their notable phototoxic properties upon irradiation and the absence of significant metabolic activity reduction in normal VERO cells after 24 h of exposure suggest their potential efficacy in this therapeutic approach.
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| 5. |
- Chen, W., et al.
(författare)
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Enhanced efficiency of polymer solar cells by improving molecular aggregation and broadening the absorption spectra
- 2019
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Ingår i: Dyes and Pigments. - : Elsevier BV. - 0143-7208 .- 1873-3743. ; 166, s. 42-48
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Tidskriftsartikel (refereegranskat)abstract
- Alkylthio-substituted thiophene-based benzo[1,2-b:4,5-b’]dithiophene (BDT) was used to construct PBDTS-DTBT, a medium band gap donor-acceptor (D-A) polymer with 5,6-difluoro-4,7-bis[4-(2-octyldodecyl)thiophene-2-yl]benzo[c] [1,2,5]thiadiazole (DTBT). The incorporation of sulfur atoms into the side chains not only lowered the highest occupied molecular orbital (HOMO) energy level but also improved molecular aggregation and thus afforded lower band gap (1.68 eV) with full width at half maximum (FWHM) of 170 nm in comparison to that of the analogous polymer (PBDT-DTBT) without sulfur atoms in side chains. Therefore, the bulk heterojunction polymer solar cells based on PBDTS-DTBT with 2% diiodooctane (DIO) as processing additive showed a high power conversion efficiency (PCE) of 9.73% with high open-circuit voltage (V OC , 0.93 V), large short-circuit current density (J SC , 14.23 mA/cm 2 ) and high fill factor (FF, 0.735).
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| 6. |
- Chen, X., et al.
(författare)
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A unimolecular platform based on diarylethene with multiple stimuli-gated photochromism
- 2019
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Ingår i: Dyes and pigments. - : Elsevier. - 0143-7208 .- 1873-3743. ; 164, s. 91-96
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Tidskriftsartikel (refereegranskat)abstract
- The gated photochromic systems have attracted great interest in scientific researches due to their merits in the opto-electronic fields, whereas the multi-stimuli gating function in a unimolecular platform has rarely been addressed. Herein, a new strategy to realize multi-stimuli gated photochromic function was devised relying on a simple Schiff-based diarylethene derivative. The compound shows no photoswitching properties in solution under irradiation with any wavelength of light. It is noteworthy that mecury(II) ions, water and protons can trigger its photo-reactivity independently with different absorption changes, respectively. Therefore, a molecular logic circuit with four inputs, including mecury(II) ions, water, protons and UV light, was fabricated on the basis of the unimolecular platform, suggesting promise for application in multi-controlled photoswitchings. These results could be valuable for the further development of photoswitchings with multiple stimuli responses.
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| 7. |
- Danyliv, Yan, et al.
(författare)
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Carbazole-s-sulfobenzimide derivative exhibiting mechanochromic thermally activated delayed fluorescence as emitter for flexible OLEDs : Theoretical and experimental insights
- 2022
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Ingår i: Dyes and pigments. - : Elsevier. - 0143-7208 .- 1873-3743. ; 208
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Tidskriftsartikel (refereegranskat)abstract
- For the first time exploiting sulfobenzimide moiety as an acceptor unit, the new type of donor-sigma-acceptor emitter exhibiting thermally activated delayed fluorescence (TADF) is demonstrated. In different solutions, the synthesized compound emits light resulting from either locally excited carbazole moiety or trough-space charge transfer (exciplex-like) between carbazole and sulfobenzimide units. In the solid state, this emitter demonstrates aggregation-induced emission enhancement and different emission colours due to its different conformations. The mechanoluminescence of the donor-sigma-acceptor compound was observed and studied in detail by experimental and theoretical approaches including single-crystal and powder X-ray analyses. Electroluminescence of the different colours was observed when the compound was utilized as non-doped TADF emitter in rigid and flexible organic light-emitting diodes fabricated on glass or poly(ethylene terephthalate) substrates. The device fabricated on the rigid substrate exhibited the best performance with maximum current efficiency, power efficiency, and external quantum efficiency of 11.0 cd A(-1), 3.0 lm W-1, and 4.3%, respectively.
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| 8. |
- Deligkiozi, Ioanna, et al.
(författare)
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Synthesis and characterization of new azobenzene-containing bis pentacyanoferrate(II) stoppered push-pull [2]rotaxanes, with alpha- and beta-cyclodextrin. Towards highly medium responsive dyes
- 2015
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Ingår i: Dyes and pigments. - : Elsevier BV. - 0143-7208 .- 1873-3743. ; 113, s. 709-722
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Tidskriftsartikel (refereegranskat)abstract
- The solvatochromic behavior of novel synthesized azo-containing viologen-based rotaxanes, combining push-pull linear and alpha or beta-cyclodextrin macrocyclic components is examined. These rotaxanes are stoppered by pentacyanoferrate(II) units. The latter stabilize these systems and furthermore act as strong electron donors. These units are linked to strong electron withdrawing viologen units thus giving rise to an exceptionally intense solvatochromic behavior. Suitable solvent polarity scales and Linear Solvation Energy Relationships (LSERs) were employed in order to rationalize the solvent polarity effects observed, both specific and non-specific ones. The results for the title compounds as well as their Cyclodextrin-Free-Dumbbell (CFD) like analogue, are compared to recent published solvatochromic data regarding similar smaller pentacyanoferrate(II) complexes as well as other highly solvatochromic compounds. Structural effects on the solvatochromic intensity as well as the contribution of different solvent-solute interactions are rationalized and quantified. (C) 2014 Elsevier Ltd. All rights reserved.
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| 9. |
- Deska, Radoslaw, et al.
(författare)
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Two-photon excited luminescence and second-harmonic generation in quinacridone microstructures
- 2020
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Ingår i: Dyes and pigments. - : ELSEVIER SCI LTD. - 0143-7208 .- 1873-3743. ; 177
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Tidskriftsartikel (refereegranskat)abstract
- Nonlinear optical microscopy was employed to investigate the properties of microstructures of quinacridone, a hydrogen-bonded pigment, derivative of quinacridine. Recently, quinacridone hierarchical microstructures (mu-QNC) having different nature-inspired morphologies were reported, e.g. in the shape of hedgehogs formed by self-assembled nano-needles. We find that such microcrystals have structure-dependent linear optical properties and exhibit strong two-photon excited fluorescence when irradiated with a near-infrared femtosecond laser. mu-QNCs exhibit different nonlinear optical properties for different crystal structures, including the emergence of symmetry-forbidden second-harmonic generation.
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| 10. |
- Du, Siying, et al.
(författare)
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Nonfullerene acceptors from thieno[3,2-b]thiophene-fused naphthalene donor core with six-member-ring connection for efficient organic solar cells
- 2021
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Ingår i: Dyes and Pigments. - : Elsevier BV. - 0143-7208 .- 1873-3743. ; 185
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Tidskriftsartikel (refereegranskat)abstract
- Comprehensive design ideas on the fused-ring donor-core in state-of-the-art acceptor-donor-acceptor (A-D-A) nonfullerene acceptors (NFAs) are still of great importance for regulating the electron push-pull effect for the sake of optimal light-harvesting, frontier molecular orbital levels, and finally their photovoltaic properties. Herein, thieno[3,2-b]thiophenes were fused in bay-area of naphthalene via six-member-ring connection, resulting in the formation of dihydropyrenobisthieno[3,2-b]thiophene based octacyclic ladder-type donor core, which was flanked by two 1,1-dicyanomethylene-3-indanone (IC) acceptor motifs with and without 5,6-diflourination, namely PTT-IC and PTT-2FIC, respectively, as novel efficient A-D-A fused-ring electron acceptors (FREAs). Compared with PTT-IC, fluorinated PTT-2FIC possesses narrower optical bandgap of 1.48 eV, better π-π stacking, and its PBDB-T:PTT-2FIC blend film exhibited better morphology, and better hole and electron mobility. As a result, nonfullerene solar cells using PBDB-T:PTT-2FIC as the active layer achieved a decent PCE of 10.40%, with an open-circuit voltage (VOC) of 0.87 V, a fill factor (FF) of 0.65, and a much higher short-circuit current (JSC) of 18.26 mA/cm2. Meanwhile, the PBDB-T:PTT-IC cells delivered a lower JSC of 12.58 mA/cm2 but a higher VOC of 0.99 V, thus resulting in a PCE of 7.39% due to its wider optical bandgap of 1.58 eV and higher LUMO energy level. These results demonstrated that NFAs based on fused-ring donor core from fusing thieno[3,2-b]thiophenes with naphthalene via six-member-ring connection are promising for organic photovoltaic applications.
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