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Issue 33, 2019
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Synthesis of an isomerically pure thienoquinoid for unipolar n-type conjugated polymers: effect of backbone curvature on charge transport performance

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Abstract

A single-isomer of the thienoquinoidal unit, IDOTT, has been synthesized via a new synthetic route involving regioselective nucleophilic addition, dihydroxylation, dehydrogenation, oxidation and isomerization, and the structure of IDOTT was unambiguously confirmed by X-ray crystallographic analysis. Compared with the reported synthetic route, this newly developed strategy possessed a wide range of substrate applicability. Moreover, IDOTT showed good air stability and excellent compatibility to chemical reactions, endowing the potential to construct conjugated polymers by different cross-coupling reactions. With IDOTT as the acceptor unit, three donor–acceptor (D–A) conjugated polymers, i.e. PIDOTT-T, PIDOTT-TT and PIDOTT-BT, were synthesized by Stille polycondensation. These three polymers showed deep highest-occupied molecular orbital (HOMO) (<−5.90 eV) and lowest unoccupied molecular orbital (LUMO) (∼−4.04 eV) energy levels, and exhibited unipolar n-type behavior in organic thin-film transistors (OTFTs). Among these polymers, PIDOTT-BT delivered the best device performance with an electron mobility of up to 0.45 cm2 V−1 s−1, which is the highest for n-type conjugated polymers with quinoidal units. The superior performance of PIDOTT-BT can be attributed to its highly ordered thin-film packing that stemmed from the small backbone curvature.

Graphical abstract: Synthesis of an isomerically pure thienoquinoid for unipolar n-type conjugated polymers: effect of backbone curvature on charge transport performance

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Publication details

The article was received on 01 Jul 2019, accepted on 29 Jul 2019 and first published on 30 Jul 2019


Article type: Paper
DOI: 10.1039/C9TC03556G
J. Mater. Chem. C, 2019,7, 10352-10359

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    Synthesis of an isomerically pure thienoquinoid for unipolar n-type conjugated polymers: effect of backbone curvature on charge transport performance

    K. Guo, B. Wu, Y. Jiang, Z. Wang, Z. Liang, Y. Li, Y. Deng and Y. Geng, J. Mater. Chem. C, 2019, 7, 10352
    DOI: 10.1039/C9TC03556G

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