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基于苯/噻吩的D-π-A发色团的合成、光学、电化学及计算研究

Synthesis, optical, electrochemical, and computational study of benzene/thiophene based D-π-A chromophores.

作者信息

Babejová Michaela, Třísková Iveta, Trnková Libuše, Semrád Hugo, Munzarová Markéta, Heger Dominik, Nachtigallová Dana, Potáček Milan

机构信息

Department of Chemistry, Faculty of Science, Masaryk University Kotlářská 2 CZ 611 37 Brno Czech Republic

Institute of Organic Chemistry and Biochemistry of the CAS Flemingovo nám. 2 160 00 Praha 6 Czech Republic.

出版信息

RSC Adv. 2024 Nov 5;14(48):35424-35437. doi: 10.1039/d4ra02668c. eCollection 2024 Nov 4.

DOI:10.1039/d4ra02668c
PMID:39502185
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11537213/
Abstract

We report the design, synthesis, electrochemical, UV-vis, fluorescence, and computational study of nine π-linked donor-acceptor (D-π-A) chromophores. The series of novel compounds comprises a terphenyl, terthiophene, or 2,5-diphenyl thiophene linker, with one electron-donating group (methyl or ,-diethyl) and one electron-withdrawing group (nitrone, formyl, or dicyanovinyl) at opposite ends of the molecule. The HOMO-LUMO gaps were determined cyclic voltammetry and found to correspond well to DFT-calculated values. Furthermore, the influence of the π-linker character and substituent on the HOMO-LUMO gap was analysed and interpreted in terms of MO composition DFT.

摘要

我们报告了对九种π-连接的供体-受体（D-π-A）发色团的设计、合成、电化学、紫外-可见光谱、荧光和计算研究。该系列新型化合物包含一个三联苯、三噻吩或2,5-二苯基噻吩连接基，在分子的相对两端分别有一个供电子基团（甲基或二乙基）和一个吸电子基团（硝酮、甲酰基或二氰基乙烯基）。通过循环伏安法测定了最高占据分子轨道（HOMO）-最低未占据分子轨道（LUMO）能隙，发现其与密度泛函理论（DFT）计算值吻合良好。此外，根据DFT的分子轨道组成，分析并解释了π-连接基特性和取代基对HOMO-LUMO能隙的影响。

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