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Issue 9, 2013
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Comparative studies on the electrochemical and optical properties of representative benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole, [1,2,5]-thiadiazolo[3,4-g]quinoxaline and pyrazino[2,3-g]quinoxaline derivatives

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Abstract

We report the synthesis and characterization of a series of structurally correlated benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole, [1,2,5]-thiadiazolo[3,4-g]quinoxaline and pyrazino[2,3-g]quinoxaline derivatives using our previously published improved synthetic methods, in order to better understand the effect of different substituents and core structures on their electrochemical and optical properties with the detailed analysis with density functional theory. Depending upon the interplay between the quinoid character, cross-conjugation, and the aromaticity of the core, these compounds exhibit tunable electronic structures, with energy gaps varying from 1.3 eV to 2.4 eV. This work marks a forward step towards the rational design of new materials for electronic and optical applications.

Graphical abstract: Comparative studies on the electrochemical and optical properties of representative benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole, [1,2,5]-thiadiazolo[3,4-g]quinoxaline and pyrazino[2,3-g]quinoxaline derivatives

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Publication details

The article was received on 17 Sep 2012, accepted on 04 Jan 2013 and first published on 08 Jan 2013


Article type: Paper
DOI: 10.1039/C2TC00212D
Citation: J. Mater. Chem. C, 2013,1, 1745-1752
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    Comparative studies on the electrochemical and optical properties of representative benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole, [1,2,5]-thiadiazolo[3,4-g]quinoxaline and pyrazino[2,3-g]quinoxaline derivatives

    H. Li, F. Zhou, T. L. D. Tam, Y. M. Lam, S. G. Mhaisalkar, H. Su and A. C. Grimsdale, J. Mater. Chem. C, 2013, 1, 1745
    DOI: 10.1039/C2TC00212D

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