Thiophene-S,S-dioxidized Indophenine: A Quinoid-Type Building Block with High Electron Affinity for Constructing n-Type Polymer Semiconductors with Narrow Band Gaps
Dr. Yunfeng Deng
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorBin Sun
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorYinghui He
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorJesse Quinn
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorDr. Chang Guo
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. Yuning Li
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorDr. Yunfeng Deng
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorBin Sun
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorYinghui He
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorJesse Quinn
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorDr. Chang Guo
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. Yuning Li
Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1 Canada
Search for more papers by this authorAbstract
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 cm2 V−1 s−1), despite its rather disordered chain packing.
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