Donor-acceptor type dithienylethenes derivatives based on anthraquinone and anthracene moieties: Synthesis, photochromic properties and theoretical calculations
Developing novel photoelectric functional materials based on dithienylethenes (DTEs) building block has drawn increasing attention due to their excellent photochromic properties. In this contribution, two D-A type DTE derivatives 3 and 4 bearing triphenylamine (TPA) and anthraquinone (or anthracene)...
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Published in | Dyes and pigments Vol. 224; p. 112000 |
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Main Authors | , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Elsevier Ltd
01.05.2024
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Subjects | |
Online Access | Get full text |
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Summary: | Developing novel photoelectric functional materials based on dithienylethenes (DTEs) building block has drawn increasing attention due to their excellent photochromic properties. In this contribution, two D-A type DTE derivatives 3 and 4 bearing triphenylamine (TPA) and anthraquinone (or anthracene) groups have been synthesized, and their structures have been characterized by means of NMR and MS. The UV–vis spectroscopy results show that compounds 3 and 4 exhibited reversible photochromism in toluene and THF solutions under UV/vis light irradiation, featuring good fatigue resistance and responsiveness. However, almost no photochromic properties for DTEs 3 and 4 were observed in larger polar DMSO. Interestingly, DTE 3 with obvious push-pull characteristics also displayed visible-light driven photochromic behavior in toluene. Meanwhile, fluorescence spectroscopy experiments have shown that DTE 4 with the anthracene fluorescent group showed fluorescent switching properties upon UV/vis light irradiation in toluene and THF solutions. The electrochemical results revealed a certain decrease in the half-wave potential of TPA-based 3 and 4 after UV irradiation, suggesting that the increasing conjugation degree of the ring-closed isomers results in the increase of HOMO orbital energy and the decrease of HOMO-LUMO gap and is beneficial for the occurrence of oxidation process, which are further proved by DFT calculations. TDDFT predicts that the transition absorption of the ring-closed isomers 3c and 4c respectively at 615 nm and 651 nm mainly come from π-π* mixed with TPA→anthraquinone CT or TPA→anthracene CT transition, which is consistent with the experimental results.
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•Two D-A type DTE derivatives have been prepared.•DTE 3 displayed visible-light driven photochromic behavior in toluene.•The anthracene-based DTE 4 showed fluorescent switching properties. |
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ISSN: | 0143-7208 1873-3743 |
DOI: | 10.1016/j.dyepig.2024.112000 |