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Synthesis and Properties of Fully-Conjugated Indacenedithiophenes.

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.

SUBMITTER: Young BS

PROVIDER: S-EPMC3979547 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Synthesis and Properties of Fully-Conjugated Indacenedithiophenes.

Young Brian S BS Chase Daniel T DT Marshall Jonathan L JL Vonnegut Chris L CL Zakharov Lev N LN Haley Michael M MM

Chemical science 20140301 3

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-elec ...[more]

PMID: 24729855

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