Issue 3, 2014

Synthesis and properties of fully-conjugated indacenedithiophenes


The synthesis and characterization of four fully-conjugated indacenedithiophenes (IDTs) are disclosed. In contrast to anthradithiophenes, regioselective synthesis of both syn and anti isomers is readily achieved. Thiophene fusion imparts increased paratropic character on the central indacene core as predicted by DFT calculations and confirmed by 1H NMR spectroscopy. IDTs exhibit red-shifted absorbance maxima with respect to their all-carbon analogues and undergo two-electron reduction and one-electron oxidation.

Graphical abstract: Synthesis and properties of fully-conjugated indacenedithiophenes

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Article type
Edge Article
19 Nov 2013
09 Dec 2013
First published
10 Dec 2013
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2014,5, 1008-1014

Synthesis and properties of fully-conjugated indacenedithiophenes

B. S. Young, D. T. Chase, J. L. Marshall, C. L. Vonnegut, L. N. Zakharov and M. M. Haley, Chem. Sci., 2014, 5, 1008 DOI: 10.1039/C3SC53181C

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