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

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 DevicesState Key Laboratory of Luminescent Materials and DevicesSouth China University of Technology Guangzhou 510640 P. R. China, Institute of Materials for Optoelectronics and New EnergySchool of Materials Science and EngineeringWuhan Institute of Technology Wuhan 430205 P. R. China
  2. Institute of Polymer Optoelectronic Materials and DevicesState Key Laboratory of Luminescent Materials and DevicesSouth China University of Technology Guangzhou 510640 P. R. China
  3. Institute of Materials for Optoelectronics and New EnergySchool of Materials Science and EngineeringWuhan Institute of Technology Wuhan 430205 P. R. China
  4. Institute of Polymer Optoelectronic Materials and DevicesState Key Laboratory of Luminescent Materials and DevicesSouth China University of Technology Guangzhou 510640 P. R. China, School of Materials Science &, EngineeringTianjin University Tianjin 300350 P. R. China, Department of Physics and ORaCELNorth Carolina State University Raleigh NC 27695 USA
  5. Department of Physics and ORaCELNorth 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 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. 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, and Cao, Yong. Fri . "3,4‐Dicyanothiophene—a Versatile Building Block for Efficient Nonfullerene Polymer Solar Cells". Germany. doi: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 = {},
doi = {10.1002/aenm.201904247},
journal = {Advanced Energy Materials},
number = ,
volume = ,
place = {Germany},
year = {2020},
month = {2}
}

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Works referenced in this record:

Low-Bandgap Near-IR Conjugated Polymers/Molecules for Organic Electronics
journal, August 2015


Ternary organic solar cells offer 14% power conversion efficiency
journal, December 2017


Over 14% Efficiency in Polymer Solar Cells Enabled by a Chlorinated Polymer Donor
journal, March 2018


Energy Level Engineering of Donor Polymers via Inductive and Resonance Effects for Polymer Solar Cells: Effects of Cyano and Alkoxy Substituents
journal, September 2015


Fluorobenzotriazole (FTAZ)-Based Polymer Donor Enables Organic Solar Cells Exceeding 12% Efficiency
journal, January 2019

  • Liao, Zhihui; Xie, Yuanpeng; Chen, Lie
  • Advanced Functional Materials, Vol. 29, Issue 10
  • DOI: 10.1002/adfm.201808828

Enhanced intermolecular interactions to improve twisted polymer photovoltaic performance
journal, January 2019


Achieving over 16% efficiency for single-junction organic solar cells
journal, March 2019


A Polythiophene Derivative with Superior Properties for Practical Application in Polymer Solar Cells
journal, July 2014


Fully Solution-Processed Small Molecule Semitransparent Solar Cells: Optimization of Transparent Cathode Architecture and Four Absorbing Layers
journal, April 2016

  • Min, Jie; Bronnbauer, Carina; Zhang, Zhi-Guo
  • Advanced Functional Materials, Vol. 26, Issue 25
  • DOI: 10.1002/adfm.201505411

High-Performance Nonfullerene Polymer Solar Cells based on Imide-Functionalized Wide-Bandgap Polymers
journal, March 2017

  • Fan, Baobing; Zhang, Kai; Jiang, Xiao-Fang
  • Advanced Materials, Vol. 29, Issue 21
  • DOI: 10.1002/adma.201606396

Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers
journal, January 2015

  • Casey, Abby; Han, Yang; Fei, Zhuping
  • Journal of Materials Chemistry C, Vol. 3, Issue 2
  • DOI: 10.1039/C4TC02008A

Polythiophene: From Fundamental Perspectives to Applications
journal, November 2017

  • Kaloni, Thaneshwor P.; Giesbrecht, Patrick K.; Schreckenbach, Georg
  • Chemistry of Materials, Vol. 29, Issue 24
  • DOI: 10.1021/acs.chemmater.7b03035

A high dielectric constant non-fullerene acceptor for efficient bulk-heterojunction organic solar cells
journal, January 2018

  • Liu, Xi; Xie, Boming; Duan, Chunhui
  • Journal of Materials Chemistry A, Vol. 6, Issue 2
  • DOI: 10.1039/C7TA10136H

Characterizing morphology in organic systems with resonant soft X-ray scattering
journal, April 2015

  • Carpenter, Joshua H.; Hunt, Adrian; Ade, Harald
  • Journal of Electron Spectroscopy and Related Phenomena, Vol. 200
  • DOI: 10.1016/j.elspec.2015.05.006

Effect of Alkylsilyl Side-Chain Structure on Photovoltaic Properties of Conjugated Polymer Donors
journal, December 2017

  • Bin, Haijun; Yang, Yankang; Peng, Zhengxing
  • Advanced Energy Materials, Vol. 8, Issue 8
  • DOI: 10.1002/aenm.201702324

Random Poly(3-hexylthiophene- co -3-cyanothiophene) Copolymers via Direct Arylation Polymerization (DArP) for Organic Solar Cells with High Open-Circuit Voltage
journal, March 2014

  • Rudenko, Andrey E.; Khlyabich, Petr P.; Thompson, Barry C.
  • ACS Macro Letters, Vol. 3, Issue 4
  • DOI: 10.1021/mz5001652

A SAXS/WAXS/GISAXS Beamline with Multilayer Monochromator
journal, October 2010


Hexasubstituted Benzenes with Ultrastrong Dipole Moments
journal, February 2016

  • Wudarczyk, Jakob; Papamokos, George; Margaritis, Vasilis
  • Angewandte Chemie International Edition, Vol. 55, Issue 9
  • DOI: 10.1002/anie.201508249

Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications
journal, March 2009

  • Mishra, Amaresh; Ma, Chang-Qi; Bäuerle, Peter
  • Chemical Reviews, Vol. 109, Issue 3
  • DOI: 10.1021/cr8004229

Dramatic Inversion of Charge Polarity in Diketopyrrolopyrrole-Based Organic Field-Effect Transistors via a Simple Nitrile Group Substitution
journal, September 2014


A general relationship between disorder, aggregation and charge transport in conjugated polymers
journal, August 2013

  • Noriega, Rodrigo; Rivnay, Jonathan; Vandewal, Koen
  • Nature Materials, Vol. 12, Issue 11
  • DOI: 10.1038/nmat3722

Recent Advances in Wide-Bandgap Photovoltaic Polymers
journal, March 2017


Nonfullerene Tandem Organic Solar Cells with High Performance of 14.11%
journal, March 2018


Nitrile-substituted thienyl and phenyl units as building blocks for high performance n-type polymer semiconductors
journal, January 2015

  • Xiong, Yu; Qiao, Xiaolan; Li, Hongxiang
  • Polymer Chemistry, Vol. 6, Issue 36
  • DOI: 10.1039/C5PY00804B

An Electron Acceptor Challenging Fullerenes for Efficient Polymer Solar Cells
journal, January 2015


Single‐Junction Polymer Solar Cells with 16.35% Efficiency Enabled by a Platinum(II) Complexation Strategy
journal, May 2019


Thermostable single-junction organic solar cells with a power conversion efficiency of 14.62%
journal, March 2018


Synthesis of soluble oligothiophenes bearing cyano groups, their optical and electrochemical properties
journal, December 2010


Molecular Engineering of Conjugated Polymers for Solar Cells: An Updated Report
journal, December 2016

  • Xiao, Shengqiang; Zhang, Qianqian; You, Wei
  • Advanced Materials, Vol. 29, Issue 20
  • DOI: 10.1002/adma.201601391

Quantitative relations between interaction parameter, miscibility and function in organic solar cells
journal, February 2018


Over 16% efficiency organic photovoltaic cells enabled by a chlorinated acceptor with increased open-circuit voltages
journal, June 2019


High open-circuit voltage organic solar cells enabled by a difluorobenzoxadiazole-based conjugated polymer donor
journal, March 2019


Pathways to a New Efficiency Regime for Organic Solar Cells
journal, May 2012

  • Koster, L. Jan Anton; Shaheen, Sean E.; Hummelen, Jan C.
  • Advanced Energy Materials, Vol. 2, Issue 10
  • DOI: 10.1002/aenm.201200103

Improving the Performance and Stability of Inverted Planar Flexible Perovskite Solar Cells Employing a Novel NDI-Based Polymer as the Electron Transport Layer
journal, February 2018

  • Kim, Hong Il; Kim, Myeong-Jong; Choi, Kyoungwon
  • Advanced Energy Materials, Vol. 8, Issue 16
  • DOI: 10.1002/aenm.201702872

Recombination in polymer-fullerene bulk heterojunction solar cells
journal, December 2010


Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes
journal, May 2015

  • Fei, Zhuping; Boufflet, Pierre; Wood, Sebastian
  • Journal of the American Chemical Society, Vol. 137, Issue 21
  • DOI: 10.1021/jacs.5b02785

Exploring the origin of high optical absorption in conjugated polymers
journal, May 2016

  • Vezie, Michelle S.; Few, Sheridan; Meager, Iain
  • Nature Materials, Vol. 15, Issue 7
  • DOI: 10.1038/nmat4645

“All That Glisters Is Not Gold”: An Analysis of the Synthetic Complexity of Efficient Polymer Donors for Polymer Solar Cells
journal, January 2015

  • Po, Riccardo; Bianchi, Gabriele; Carbonera, Chiara
  • Macromolecules, Vol. 48, Issue 3
  • DOI: 10.1021/ma501894w

Polythiophene derivatives compatible with both fullerene and non-fullerene acceptors for polymer solar cells
journal, January 2019

  • Jia, Xiao'e; Chen, Zhiming; Duan, Chunhui
  • Journal of Materials Chemistry C, Vol. 7, Issue 2
  • DOI: 10.1039/C8TC04746D

Quenching to the Percolation Threshold in Organic Solar Cells
journal, February 2019


Non-fullerene acceptors for organic solar cells
journal, February 2018


Advances in Molecular Design and Synthesis of Regioregular Polythiophenes
journal, September 2008

  • Osaka, Itaru; McCullough, Richard D.
  • Accounts of Chemical Research, Vol. 41, Issue 9
  • DOI: 10.1021/ar800130s

Backbone Fluorination of Polythiophenes Improves Device Performance of Non-Fullerene Polymer Solar Cells
journal, September 2019

  • Jia, Xiao’e; Liu, Gongchu; Chen, Shanshan
  • ACS Applied Energy Materials, Vol. 2, Issue 10
  • DOI: 10.1021/acsaem.9b01532

Molecular Optimization Enables over 13% Efficiency in Organic Solar Cells
journal, May 2017

  • Zhao, Wenchao; Li, Sunsun; Yao, Huifeng
  • Journal of the American Chemical Society, Vol. 139, Issue 21
  • DOI: 10.1021/jacs.7b02677

Design rules for minimizing voltage losses in high-efficiency organic solar cells
journal, July 2018


Effect of Systematically Tuning Conjugated Donor Polymer Lowest Unoccupied Molecular Orbital Levels via Cyano Substitution on Organic Photovoltaic Device Performance
journal, July 2016


Fluorination of Polythiophene Derivatives for High Performance Organic Photovoltaics
journal, July 2014

  • Jo, Jea Woong; Jung, Jae Woong; Wang, Hsin-Wei
  • Chemistry of Materials, Vol. 26, Issue 14
  • DOI: 10.1021/cm502229k

Understanding Energy Loss in Organic Solar Cells: Toward a New Efficiency Regime
journal, January 2018


The recent progress of wide bandgap donor polymers towards non-fullerene organic solar cells
journal, April 2019


Chlorinated Wide-Bandgap Donor Polymer Enabling Annealing Free Nonfullerene Solar Cells with the Efficiency of 11.5%
journal, November 2018


Single-Junction Organic Solar Cell with over 15% Efficiency Using Fused-Ring Acceptor with Electron-Deficient Core
journal, April 2019


n-Type conjugated polymers based on 3,3′-dicyano-2,2′-bithiophene: synthesis and semiconducting properties
journal, January 2018

  • Sui, Ying; Deng, Yunfeng; Han, Yang
  • Journal of Materials Chemistry C, Vol. 6, Issue 47
  • DOI: 10.1039/C8TC03725F

In Situ Characterization of Polymer–Fullerene Bilayer Stability
journal, January 2015

  • Leman, Deborah; Kelly, Mary Allison; Ness, Stuart
  • Macromolecules, Vol. 48, Issue 2
  • DOI: 10.1021/ma5021227

Organic solar cells based on non-fullerene acceptors
journal, January 2018

  • Hou, Jianhui; Inganäs, Olle; Friend, Richard H.
  • Nature Materials, Vol. 17, Issue 2
  • DOI: 10.1038/nmat5063

Fine-tuning of the chemical structure of photoactive materials for highly efficient organic photovoltaics
journal, October 2018


Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications
journal, April 2011

  • Cardona, Claudia M.; Li, Wei; Kaifer, Angel E.
  • Advanced Materials, Vol. 23, Issue 20
  • DOI: 10.1002/adma.201004554

Organic and solution-processed tandem solar cells with 17.3% efficiency
journal, August 2018


Nonfullerene Acceptor Molecules for Bulk Heterojunction Organic Solar Cells
journal, February 2018


Recent Advances in Bulk Heterojunction Polymer Solar Cells
journal, August 2015


Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions
journal, December 1995


Improved Charge Transport and Reduced Nonradiative Energy Loss Enable Over 16% Efficiency in Ternary Polymer Solar Cells
journal, June 2019


A Study of the Degree of Fluorination in Regioregular Poly(3-hexylthiophene)
journal, December 2016


A Wide Band Gap Polymer with a Deep Highest Occupied Molecular Orbital Level Enables 14.2% Efficiency in Polymer Solar Cells
journal, May 2018

  • Li, Sunsun; Ye, Long; Zhao, Wenchao
  • Journal of the American Chemical Society, Vol. 140, Issue 23
  • DOI: 10.1021/jacs.8b02695

Fullerene-Free Polymer Solar Cells with over 11% Efficiency and Excellent Thermal Stability
journal, April 2016

  • Zhao, Wenchao; Qian, Deping; Zhang, Shaoqing
  • Advanced Materials, Vol. 28, Issue 23
  • DOI: 10.1002/adma.201600281

Polymer Donors for High-Performance Non-Fullerene Organic Solar Cells
journal, January 2019

  • Fu, Huiting; Wang, Zhaohui; Sun, Yanming
  • Angewandte Chemie International Edition, Vol. 58, Issue 14
  • DOI: 10.1002/anie.201806291

Next-generation organic photovoltaics based on non-fullerene acceptors
journal, February 2018


Low Optical Bandgap Polythiophenes by an Alternating Donor/Acceptor Repeat Unit Strategy
journal, May 1997

  • Zhang, Qing T.; Tour, James M.
  • Journal of the American Chemical Society, Vol. 119, Issue 21
  • DOI: 10.1021/ja9640399

Cyano-substituted benzochalcogenadiazole-based polymer semiconductors for balanced ambipolar organic thin-film transistors
journal, January 2018

  • Shi, Shengbin; Wang, Hang; Chen, Peng
  • Polymer Chemistry, Vol. 9, Issue 28
  • DOI: 10.1039/C8PY00540K

Fullerene-free polymer solar cell based on a polythiophene derivative with an unprecedented energy loss of less than 0.5 eV
journal, January 2016

  • Zhang, Hao; Li, Sunsun; Xu, Bowei
  • Journal of Materials Chemistry A, Vol. 4, Issue 46
  • DOI: 10.1039/C6TA07672F

Achieving Over 15% Efficiency in Organic Photovoltaic Cells via Copolymer Design
journal, February 2019


Dicyanobenzothiadiazole Derivatives Possessing Switchable Dielectric Permittivities
journal, June 2017

  • Wudarczyk, Jakob; Papamokos, George; Marszalek, Tomasz
  • ACS Applied Materials & Interfaces, Vol. 9, Issue 24
  • DOI: 10.1021/acsami.7b03060

Effect of Temperature and Illumination on the Electrical Characteristics of Polymer–Fullerene Bulk-Heterojunction Solar Cells
journal, January 2004

  • Riedel, I.; Parisi, J.; Dyakonov, V.
  • Advanced Functional Materials, Vol. 14, Issue 1
  • DOI: 10.1002/adfm.200304399

The Crucial Role of Chlorinated Thiophene Orientation in Conjugated Polymers for Photovoltaic Devices
journal, August 2018

  • Wu, Yanan; An, Cunbin; Shi, Lanlan
  • Angewandte Chemie International Edition, Vol. 57, Issue 39
  • DOI: 10.1002/anie.201807865

Effect of synthetic accessibility on the commercial viability of organic photovoltaics
journal, January 2013

  • Osedach, Timothy P.; Andrew, Trisha L.; Bulović, Vladimir
  • Energy & Environmental Science, Vol. 6, Issue 3
  • DOI: 10.1039/c3ee24138f