Synthesis and properties of fully-conjugated indacenedithiophenes

• DOI: 10.1039/c3sc53181c
• Publication Date: 2013-12-10T14:32:49Z
• Authors: Brian S. Young; Daniel T. Chase; Jonathan L. Marshall; Chris L. Vonnegut; Lev N. Zakharov; Michael M. Haley
• Keywords: Absorbance

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