title: Thiophene-S,S-dioxidized Indophenine: A Quinoid-Type Building Block with High Electron Affinity for Constructing n-Type Polymer Semiconductors with Narrow Band Gaps.
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.
authors.affiliation: Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1, Canada.
authors.forename: Yunfeng
authors.initials: Y
authors.lastname: Deng
authors.affiliation: Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1, Canada.
authors.forename: Bin
authors.initials: B
authors.lastname: Sun
authors.affiliation: Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1, Canada.
authors.forename: Yinghui
authors.initials: Y
authors.lastname: He
authors.affiliation: Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1, Canada.
authors.forename: Jesse
authors.initials: J
authors.lastname: Quinn
authors.affiliation: Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1, Canada.
authors.forename: Chang
authors.initials: C
authors.lastname: Guo
authors.affiliation: Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Ave West, Waterloo, Ontario, N2L 3G1, Canada. yuning.li@uwaterloo.ca.
authors.forename: Yuning
authors.initials: Y
authors.lastname: Li
keywords: isomers; molecular electronics; polymers; semiconductors; structure elucidation