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Synthesis and Properties of Fully-Conjugated Indacenedithiophenes
Brian S Young1, Daniel T Chase1, Jonathan L Marshall1
1Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, USA.
Abstract:
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.
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