Issue 44, 2011

Substituent effect on the electronic properties of pyrazino[2,3-g] quinoxaline molecules

Abstract

We report the synthesis and characterization of pyrazino[2,3-g]quinoxaline derivatives with a systematic change in the substituents at the 2, 3, 7 and 8 positions and with or without 2-thienyl at the 5 and 10 positions to study the substituent effect and quinoid character of such a system. We performed density functional theory calculations using the B3LYP functional and 6-31G* basis set under the geometry optimization condition, together with the resonance effect of a valence bond theory to understand the electronic structures of these molecules. It was found that a combination of conjugation and cross-conjugation effects is responsible for the observed trends in their electronic properties, thus giving insights into designing molecules utilizing such effects.

Graphical abstract: Substituent effect on the electronic properties of pyrazino[2,3-g] quinoxaline molecules

Supplementary files

Article information

Article type
Paper
Submitted
26 May 2011
Accepted
08 Sep 2011
First published
11 Oct 2011

J. Mater. Chem., 2011,21, 17798-17804

Substituent effect on the electronic properties of pyrazino[2,3-g] quinoxaline molecules

T. L. Tam, F. Zhou, H. Li, J. C. Yu Pang, Y. M. Lam, S. G. Mhaisalkar, H. Su and A. C. Grimsdale, J. Mater. Chem., 2011, 21, 17798 DOI: 10.1039/C1JM12347E

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