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Thiophene-S,S-dioxidized Indophenine: A Quinoid-Type Building Block with High Electron Affinity for Constructing
Yunfeng Deng1, Bin Sun1, Yinghui He1
1Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1, Canada.
Abstract:
Three thiophene-S,S-dioxidized indophenine (IDTO) isomers, 3 a (E,E,E), 3 b (Z,E,E), and 3 c (Z,E,Z), were synthesized by oxidation of an indophenine compound. 3 b and 3 c could be converted into the most-stable 3 a by heating at 110 °C. An IDTO-containing conjugated polymer, PIDTOTT, was prepared using 3 a as a comonomer through a Stille coupling reaction, and it possesses a narrow band gap and low energy levels. In organic field effect transistors (OFETs), PIDTOTT exhibited unipolar n-type semiconductor characteristics with unexpectedly high electron mobility (up to 0.14 cm(2) V(-1) s(-1)), despite its rather disordered chain packing.
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