para-Azaquinodimethane: A Compact Quinodimethane Variant as an Ambient Stable Building Block for High-Performance Low Band Gap Polymers

Liu, Xuncheng; He, Bo; Anderson, Christopher L.; Kang, Jun; Chen, Teresa; Chen, Jinxiang; Feng, Shizhen; Zhang, Lianjie; Kolaczkowski, Matthew A.; Teat, Simon J.; Brady, Michael A.; Zhu, Chenhui; Wang, Lin -Wang; Chen, Junwu; Liu, Yi

doi:10.1021/jacs.7b04031

para-Azaquinodimethane: A Compact Quinodimethane Variant as an Ambient Stable Building Block for High-Performance Low Band Gap Polymers

Journal Article · Wed May 24 00:00:00 EDT 2017 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.7b04031· OSTI ID:1379892

^[1]; ^[2]; Anderson, Christopher L. ^[3]; Kang, Jun ^[2]; Chen, Teresa ^[2]; Chen, Jinxiang ^[4]; Feng, Shizhen ^[4]; Zhang, Lianjie ^[4]; Kolaczkowski, Matthew A. ^[3]; Teat, Simon J. ^[2]; Brady, Michael A. ^[2]; Zhu, Chenhui ^[2]; Wang, Lin -Wang ^[2]; Chen, Junwu ^[4]; ^[2]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); South China Univ. of Technology, Guangzhou (People's Republic of China)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)
South China Univ. of Technology, Guangzhou (People's Republic of China)

Quinoidal structures incorporating expanded para-quinodimethane (p-QM) units have garnered great interest as functional organic electronic, optical, and magnetic materials. The direct use of the compact p-QM unit as an electronic building block, however, has been inhibited by the high reactivity conveyed by its biradical character. Herein, we introduce a stable p-QM variant, namely p-azaquinodimethane (p-AQM), that incorporates nitrogen atoms in the central ring and alkoxy substituents on the periphery to increase the stability of the quinoidal structure. The succinct synthesis from readily available precursors leads to regio- and stereospecific p-AQMs that can be readily integrated into the backbone of conjugated polymers. The quinoidal character of the p-AQM unit endows the resulting polymers with narrow band gaps and high carrier transport mobilities. The study of a series of copolymers employing different numbers of thiophene units revealed an unconventional trend in band gaps, which is distinct from the widely adopted donor-acceptor approach to tuning the band gaps of conjugated polymers. Theoretical calculations have shed light on the nature of this trend, which may provide a unique class of conjugated polymers with promising optical and electronic properties.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1379892

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 24 Vol. 139; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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para-Azaquinodimethane: A Compact Quinodimethane Variant as an Ambient Stable Building Block for High-Performance Low Band Gap Polymers

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