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Title: 3,4‐Dicyanothiophene—a Versatile Building Block for Efficient Nonfullerene Polymer Solar Cells

Abstract

Abstract In this contribution, a versatile building block, 3,4‐dicyanothiophene (DCT), which possesses structural simplicity and synthetic accessibility for constructing high‐performance, low‐cost, wide‐bandgap conjugated polymers for use as donors in polymer solar cells (PSCs), is reported. A prototype polymer, PB3TCN‐C66, and its cyano‐free analogue polymer PB3T‐C66, are synthesized to evaluate the potential of using DCT in nonfullerene PSCs. A stronger aggregation property in solution, higher thermal transition temperatures with higher enthalpies, a larger dipole moment, higher relative dielectric constant, and more linear conformation are exhibited by PB3TCN‐C66. Solar cells employing IT‐4F as the electron acceptor offer power conversion efficiencies (PCEs) of 11.2% and 2.3% for PB3TCN‐C66 and PB3T‐C66, respectively. Morphological characterizations reveal that the PB3TCN‐C66:IT‐4F blend exhibits better π–π paracrystallinity, a contracted domain size, and higher phase purity, consistent with its higher molecular interaction parameter, derived from thermodynamic calculations. Moreover, PB3TCN‐C66 offers a higher open‐circuit voltage and reduced energy loss than most state‐of‐the‐art wide‐bandgap polymers, without the need of additional electron‐withdrawing substituents. Two additional polymers derived from DCT also demonstrate promising performance with a higher PCE of 13.4% being achieved. Thus, DCT represents a versatile and promising building block for constructing high‐performance, low‐cost, conjugated polymers for application in PSCs.

Authors:
 [1];  [2];  [2];  [2];  [2];  [2];  [2];  [3];  [2];  [4];  [5];  [3];  [2]; ORCiD logo [2];  [2];  [2]
  1. Institute of Polymer Optoelectronic Materials and Devices State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou 510640 P. R. China, Institute of Materials for Optoelectronics and New Energy School of Materials Science and Engineering Wuhan Institute of Technology Wuhan 430205 P. R. China
  2. Institute of Polymer Optoelectronic Materials and Devices State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou 510640 P. R. China
  3. Institute of Materials for Optoelectronics and New Energy School of Materials Science and Engineering Wuhan Institute of Technology Wuhan 430205 P. R. China
  4. Institute of Polymer Optoelectronic Materials and Devices State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou 510640 P. R. China, School of Materials Science &, Engineering Tianjin University Tianjin 300350 P. R. China, Department of Physics and ORaCEL North Carolina State University Raleigh NC 27695 USA
  5. Department of Physics and ORaCEL North Carolina State University Raleigh NC 27695 USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1598374
Grant/Contract Number:  
DE‐AC02‐05CH11231
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Advanced Energy Materials
Additional Journal Information:
Journal Name: Advanced Energy Materials Journal Volume: 10 Journal Issue: 12; Journal ID: ISSN 1614-6832
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Zhang, Bo, Yu, Yonggao, Zhou, Jiadong, Wang, Zhenfeng, Tang, Haoran, Xie, Shenkun, Xie, Zengqi, Hu, Liuyong, Yip, Hin‐Lap, Ye, Long, Ade, Harald, Liu, Zhitian, He, Zhicai, Duan, Chunhui, Huang, Fei, and Cao, Yong. 3,4‐Dicyanothiophene—a Versatile Building Block for Efficient Nonfullerene Polymer Solar Cells. Germany: N. p., 2020. Web. doi:10.1002/aenm.201904247.
Zhang, Bo, Yu, Yonggao, Zhou, Jiadong, Wang, Zhenfeng, Tang, Haoran, Xie, Shenkun, Xie, Zengqi, Hu, Liuyong, Yip, Hin‐Lap, Ye, Long, Ade, Harald, Liu, Zhitian, He, Zhicai, Duan, Chunhui, Huang, Fei, & Cao, Yong. 3,4‐Dicyanothiophene—a Versatile Building Block for Efficient Nonfullerene Polymer Solar Cells. Germany. https://doi.org/10.1002/aenm.201904247
Zhang, Bo, Yu, Yonggao, Zhou, Jiadong, Wang, Zhenfeng, Tang, Haoran, Xie, Shenkun, Xie, Zengqi, Hu, Liuyong, Yip, Hin‐Lap, Ye, Long, Ade, Harald, Liu, Zhitian, He, Zhicai, Duan, Chunhui, Huang, Fei, and Cao, Yong. Fri . "3,4‐Dicyanothiophene—a Versatile Building Block for Efficient Nonfullerene Polymer Solar Cells". Germany. https://doi.org/10.1002/aenm.201904247.
@article{osti_1598374,
title = {3,4‐Dicyanothiophene—a Versatile Building Block for Efficient Nonfullerene Polymer Solar Cells},
author = {Zhang, Bo and Yu, Yonggao and Zhou, Jiadong and Wang, Zhenfeng and Tang, Haoran and Xie, Shenkun and Xie, Zengqi and Hu, Liuyong and Yip, Hin‐Lap and Ye, Long and Ade, Harald and Liu, Zhitian and He, Zhicai and Duan, Chunhui and Huang, Fei and Cao, Yong},
abstractNote = {Abstract In this contribution, a versatile building block, 3,4‐dicyanothiophene (DCT), which possesses structural simplicity and synthetic accessibility for constructing high‐performance, low‐cost, wide‐bandgap conjugated polymers for use as donors in polymer solar cells (PSCs), is reported. A prototype polymer, PB3TCN‐C66, and its cyano‐free analogue polymer PB3T‐C66, are synthesized to evaluate the potential of using DCT in nonfullerene PSCs. A stronger aggregation property in solution, higher thermal transition temperatures with higher enthalpies, a larger dipole moment, higher relative dielectric constant, and more linear conformation are exhibited by PB3TCN‐C66. Solar cells employing IT‐4F as the electron acceptor offer power conversion efficiencies (PCEs) of 11.2% and 2.3% for PB3TCN‐C66 and PB3T‐C66, respectively. Morphological characterizations reveal that the PB3TCN‐C66:IT‐4F blend exhibits better π–π paracrystallinity, a contracted domain size, and higher phase purity, consistent with its higher molecular interaction parameter, derived from thermodynamic calculations. Moreover, PB3TCN‐C66 offers a higher open‐circuit voltage and reduced energy loss than most state‐of‐the‐art wide‐bandgap polymers, without the need of additional electron‐withdrawing substituents. Two additional polymers derived from DCT also demonstrate promising performance with a higher PCE of 13.4% being achieved. Thus, DCT represents a versatile and promising building block for constructing high‐performance, low‐cost, conjugated polymers for application in PSCs.},
doi = {10.1002/aenm.201904247},
journal = {Advanced Energy Materials},
number = 12,
volume = 10,
place = {Germany},
year = {Fri Feb 07 00:00:00 EST 2020},
month = {Fri Feb 07 00:00:00 EST 2020}
}

Journal Article:
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https://doi.org/10.1002/aenm.201904247

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