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Thiophene‐ S , S ‐dioxidized Indophenine: A Quinoid‐Type Building Block with High Electron Affinity for Constructing n‐Type Polymer Semiconductors with Narrow Band Gaps
Author(s) -
Deng Yunfeng,
Sun Bin,
He Yinghui,
Quinn Jesse,
Guo Chang,
Li Yuning
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201508781
Subject(s) - thiophene , stille reaction , comonomer , semiconductor , conjugated system , band gap , organic semiconductor , materials science , polymer , electron mobility , crystallography , block (permutation group theory) , electron , electron affinity (data page) , polymer chemistry , chemistry , stereochemistry , optoelectronics , copolymer , organic chemistry , molecule , physics , geometry , mathematics , quantum mechanics
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.