Pyrazine-Flanked Diketopyrrolopyrrole (DPP): A New Polymer Building Block for High-Performance n-Type Organic Thermoelectrics
Abstract
n-Doped conjugated polymers usually show low electrical conductivities and low thermoelectric power factors, limiting their applications in n-type organic thermoelectrics. Here, we report the synthesis of a new diketopyrrolopyrrole (DPP) derivative, pyrazine-flanked DPP (PzDPP), with the deepest LUMO level in all the reported DPP derivatives. Based on PzDPP, a donor–acceptor copolymer, P(PzDPP-CT2), is synthesized. The polymer displays a deep LUMO energy level and strong interchain interaction with a short π–π stacking distance of 3.38 Å. When doped with n-dopant N-DMBI, P(PzDPP-CT2) exhibits high n-type electrical conductivities of up to 8.4 S cm–1 and power factors of up to 57.3 μW m–1 K–2. These values are much higher than previously reported n-doped DPP polymers, and the power factor also ranks the highest in solution-processable n-doped conjugated polymers. These results suggest that PzDPP is a promising high-performance building block for n-type organic thermoelectrics and also highlight that, without sacrificing polymer interchain interactions, efficient n-doping can be realized in conjugated polymers with careful molecular engineering.
- Authors:
-
[1];
[1];
[2];
[1]
- Peking Univ., Beijing (China)
- Univ. of Southern Mississippi, Hattiesburg, MS (United States)
- Publication Date:
- Research Org.:
- Univ. of Southern Mississippi, Hattiesburg, MS (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1774739
- Alternate Identifier(s):
- OSTI ID: 1985421
- Grant/Contract Number:
- SC0019361
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of the American Chemical Society
- Additional Journal Information:
- Journal Volume: 141; Journal Issue: 51; Journal ID: ISSN 0002-7863
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Plastics; Electrical conductivity; Differential pulse voltammetry; Conjugated polymers; Polymers
Citation Formats
Yan, Xinwen, Xiong, Miao, Li, Jia-Tong, Zhang, Song, Ahmad, Zachary, Lu, Yang, Wang, Zi-Yuan, Yao, Ze-Fan, Wang, Jie-Yu, Gu, Xiaodan, and Lei, Ting. Pyrazine-Flanked Diketopyrrolopyrrole (DPP): A New Polymer Building Block for High-Performance n-Type Organic Thermoelectrics. United States: N. p., 2019.
Web. doi:10.1021/jacs.9b10107.
Yan, Xinwen, Xiong, Miao, Li, Jia-Tong, Zhang, Song, Ahmad, Zachary, Lu, Yang, Wang, Zi-Yuan, Yao, Ze-Fan, Wang, Jie-Yu, Gu, Xiaodan, & Lei, Ting. Pyrazine-Flanked Diketopyrrolopyrrole (DPP): A New Polymer Building Block for High-Performance n-Type Organic Thermoelectrics. United States. https://doi.org/10.1021/jacs.9b10107
Yan, Xinwen, Xiong, Miao, Li, Jia-Tong, Zhang, Song, Ahmad, Zachary, Lu, Yang, Wang, Zi-Yuan, Yao, Ze-Fan, Wang, Jie-Yu, Gu, Xiaodan, and Lei, Ting. Wed .
"Pyrazine-Flanked Diketopyrrolopyrrole (DPP): A New Polymer Building Block for High-Performance n-Type Organic Thermoelectrics". United States. https://doi.org/10.1021/jacs.9b10107. https://www.osti.gov/servlets/purl/1774739.
@article{osti_1774739,
title = {Pyrazine-Flanked Diketopyrrolopyrrole (DPP): A New Polymer Building Block for High-Performance n-Type Organic Thermoelectrics},
author = {Yan, Xinwen and Xiong, Miao and Li, Jia-Tong and Zhang, Song and Ahmad, Zachary and Lu, Yang and Wang, Zi-Yuan and Yao, Ze-Fan and Wang, Jie-Yu and Gu, Xiaodan and Lei, Ting},
abstractNote = {n-Doped conjugated polymers usually show low electrical conductivities and low thermoelectric power factors, limiting their applications in n-type organic thermoelectrics. Here, we report the synthesis of a new diketopyrrolopyrrole (DPP) derivative, pyrazine-flanked DPP (PzDPP), with the deepest LUMO level in all the reported DPP derivatives. Based on PzDPP, a donor–acceptor copolymer, P(PzDPP-CT2), is synthesized. The polymer displays a deep LUMO energy level and strong interchain interaction with a short π–π stacking distance of 3.38 Å. When doped with n-dopant N-DMBI, P(PzDPP-CT2) exhibits high n-type electrical conductivities of up to 8.4 S cm–1 and power factors of up to 57.3 μW m–1 K–2. These values are much higher than previously reported n-doped DPP polymers, and the power factor also ranks the highest in solution-processable n-doped conjugated polymers. These results suggest that PzDPP is a promising high-performance building block for n-type organic thermoelectrics and also highlight that, without sacrificing polymer interchain interactions, efficient n-doping can be realized in conjugated polymers with careful molecular engineering.},
doi = {10.1021/jacs.9b10107},
journal = {Journal of the American Chemical Society},
number = 51,
volume = 141,
place = {United States},
year = {Wed Nov 27 00:00:00 EST 2019},
month = {Wed Nov 27 00:00:00 EST 2019}
}
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