Issue 9, 2011

Structure-property relationships in conjugated donor–acceptor systems functionalized with tetrathiafulvalene

Abstract

The properties of two donor–acceptor compounds tetrathiafulvalene-acenaphtho[1,2-b] quinoxaline (1) and tetrathiafulvalene-3-nitro-acenaphtho[1,2-b]quinoxaline (2) have been investigated by solution-state studies (electrochemistry, absorption, self-assembly) and theoretical calculations (DFT, TD-DFT). The electrochemical studies indicate the nitro-substituted effect on their redox properties is negligible. Both compounds show effective intramolecular charge transfer (ICT) transitions in the UV-Visible range in solution. Compared with compound 1, compound 2 has a bathochromic shift in the absorption spectra, the λmax−ICT has been extended from 20 800 cm−1 to 19 700 cm−1 (480 nm to 507 nm). In addition, when the nitro group is employed, the self-assembly characteristics of the two compounds are substantially changed from ribbon-like nanostructures to root-like nanostructures. Density functional theory (DFT) calculations provide insights into their molecular geometries, electronic structures, and physico-chemical properties.

Graphical abstract: Structure-property relationships in conjugated donor–acceptor systems functionalized with tetrathiafulvalene

Article information

Article type
Paper
Submitted
02 May 2011
Accepted
27 May 2011
First published
07 Jul 2011

New J. Chem., 2011,35, 1876-1882

Structure-property relationships in conjugated donor–acceptor systems functionalized with tetrathiafulvalene

C. Jia, J. Zhang, L. Zhang and X. Yao, New J. Chem., 2011, 35, 1876 DOI: 10.1039/C1NJ20384C

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