Critical Role of Molecular Symmetry for Charge Transport Properties: A Paradigm Learned from Quinoidal Bithieno[3,4-b]thiophenes
Longbin Ren
1, 2
,
Dafei Yuan
1, 2
,
Eliot Gann
3, 4
,
Guo Yuan Yuan
1, 2
,
Lars Lykke Thomsen
3
,
Chris McNeill
4
,
Chong-an Di
1
,
Yuanping Yi
1
,
Xiaozhang Zhu
1, 2
,
Daoben Zhu
1, 2
1
Publication type: Journal Article
Publication date: 2017-05-23
scimago Q1
wos Q1
SJR: 2.065
CiteScore: 12.0
Impact factor: 7.0
ISSN: 08974756, 15205002
Materials Chemistry
General Chemistry
General Chemical Engineering
Abstract
High molecular symmetry is always observed in high-performance organic semiconductors. However, whether it is an essential factor for molecular design is unclear. In this work, we designed and synthesized three quinoidal isomers, QBTT-o, QBTT-i, and QBTT-s, with different sulfur orientations and a stable E configuration to investigate the relationship between the structure symmetry and organic thin-film transistor performance. We found that QBTT-o and QBTT-i with high C2h symmetry exhibit electron mobilities of 0.02 and 0.15 cm2 V–1 s–1, respectively, while QBTT-s exhibits an unexpectedly high electron mobility of 0.32 cm2 V–1 s–1 with Ion/Ioff ratios of ≤106. The enhanced electron mobilities from QBTT-o and QBTT-i to QBTT-s can be attributed to the different sulfur orientations, especially, molecular symmetry. The thin-film microstructures of three QBTTs were systematically investigated by grazing incidence wide-angle X-ray scattering, near-edge X-ray absorption fine structure spectroscopy, atomic force ...
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Ren L. et al. Critical Role of Molecular Symmetry for Charge Transport Properties: A Paradigm Learned from Quinoidal Bithieno[3,4-b]thiophenes // Chemistry of Materials. 2017. Vol. 29. No. 11. pp. 4999-5008.
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Ren L., Yuan D., Gann E., Yuan G. Y., Thomsen L. L., McNeill C., Di C., Yi Y., Zhu X., Zhu D. Critical Role of Molecular Symmetry for Charge Transport Properties: A Paradigm Learned from Quinoidal Bithieno[3,4-b]thiophenes // Chemistry of Materials. 2017. Vol. 29. No. 11. pp. 4999-5008.
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RIS
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TY - JOUR
DO - 10.1021/acs.chemmater.7b01551
UR - https://doi.org/10.1021/acs.chemmater.7b01551
TI - Critical Role of Molecular Symmetry for Charge Transport Properties: A Paradigm Learned from Quinoidal Bithieno[3,4-b]thiophenes
T2 - Chemistry of Materials
AU - Ren, Longbin
AU - Yuan, Dafei
AU - Gann, Eliot
AU - Yuan, Guo Yuan
AU - Thomsen, Lars Lykke
AU - McNeill, Chris
AU - Di, Chong-an
AU - Yi, Yuanping
AU - Zhu, Xiaozhang
AU - Zhu, Daoben
PY - 2017
DA - 2017/05/23
PB - American Chemical Society (ACS)
SP - 4999-5008
IS - 11
VL - 29
SN - 0897-4756
SN - 1520-5002
ER -
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@article{2017_Ren,
author = {Longbin Ren and Dafei Yuan and Eliot Gann and Guo Yuan Yuan and Lars Lykke Thomsen and Chris McNeill and Chong-an Di and Yuanping Yi and Xiaozhang Zhu and Daoben Zhu},
title = {Critical Role of Molecular Symmetry for Charge Transport Properties: A Paradigm Learned from Quinoidal Bithieno[3,4-b]thiophenes},
journal = {Chemistry of Materials},
year = {2017},
volume = {29},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/acs.chemmater.7b01551},
number = {11},
pages = {4999--5008},
doi = {10.1021/acs.chemmater.7b01551}
}
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MLA
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Ren, Longbin, et al. “Critical Role of Molecular Symmetry for Charge Transport Properties: A Paradigm Learned from Quinoidal Bithieno[3,4-b]thiophenes.” Chemistry of Materials, vol. 29, no. 11, May. 2017, pp. 4999-5008. https://doi.org/10.1021/acs.chemmater.7b01551.