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

We report the design, synthesis, electrochemical, UV-vis, fluorescence, and computational study of nine -linked donor-acceptor (D-πA) chromophores. The series of novel compounds comprises a terphenyl, terthiophene, or 2,5-diphenyl thiophene linker, with one electron-donating group (methyl or p-N , N...

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Bibliographic Details
Published in:RSC advances 2024-11, Vol.14 (48), p.35424-35437
Main Authors: Babejová, Michaela, T ísková, Iveta, Trnková, Libuše, Semrád, Hugo, Munzarová, Markéta, Heger, Dominik, Nachtigallová, Dana, Potá ek, Milan
Format: Article
Language:English
Subjects:
Benzene
Chemistry
Chromophores
Molecular orbitals
Synthesis
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Summary:We report the design, synthesis, electrochemical, UV-vis, fluorescence, and computational study of nine -linked donor-acceptor (D-πA) chromophores. The series of novel compounds comprises a terphenyl, terthiophene, or 2,5-diphenyl thiophene linker, with one electron-donating group (methyl or p-N , N -diethyl) and one electron-withdrawing group (nitrone, formyl, or dicyanovinyl) at opposite ends of the molecule. The HOMO-LUMO gaps were determined via 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 via DFT. Synthesis of novel (D-π-A) chromophores with one electron-donating + withdrawing group at opposite ends of terphenyl, terthiophene, or 2,5-diphenylthiophene, analysed upon results of HOMO-LUMO gaps, determined via CV and in terms of MO via DFT.
ISSN:2046-2069
2046-2069
DOI:10.1039/d4ra02668c