Bo He (367100)

Chenhui Zhu (1352544)

Christopher L. Anderson (597034)

Jinxiang Chen (646451)

Jun Kang (627908)

Junwu Chen (1427353)

Lianjie Zhang (2065147)

Lin-Wang Wang (1234770)

Matthew A. Kolaczkowski (4090762)

Michael A. Brady (1794049)

Shizhen Feng (4090759)

Simon J. Teat (1304670)

Teresa Chen (1847608)

Xuncheng Liu (112191)

Yi Liu (36759)

Journal of the American Chemical Society

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

FigShare

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

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

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

eScholarship - University of California

English

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

Xuncheng Liu

Bo He

Christopher L. Anderson

Jun Kang

Teresa Chen

Jinxiang Chen

Shizhen Feng

Lianjie Zhang

Matthew A. Kolaczkowski

Simon J. Teat

Michael A. Brady

Chenhui Zhu

Lin-Wang Wang

Junwu Chen

Yi Liu

Crossref

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

https://figshare.com/articles/_i_para_i_-Azaquinodimethane_A_Compact_Quinodimethane_Variant_as_an_Ambient_Stable_Building_Block_for_High-Performance_Low_Band_Gap_Polymers/5084365