This content will become publicly available on Thu May 16 00:00:00 EDT 2024
Anthradithiophene (ADT)‐Based Polymerized Non‐Fullerene Acceptors for All‐Polymer Solar Cells
Abstract
Abstract Realizing efficient all‐polymer solar cell (APSC) acceptors typically involves increased building block synthetic complexity, hence potentially unscalable syntheses and/or prohibitive costs. Here we report the synthesis, characterization, and implementation in APSCs of three new polymer acceptors P1 – P3 using a scalable donor fragment, bis(2‐octyldodecyl)anthra[1,2‐b : 5,6‐b’]dithiophene‐4,10‐dicarboxylate ( ADT ) co‐polymerized with the high‐efficiency acceptor units, NDI, Y6, and IDIC. All three copolymers have comparable photophysics to known polymers; however, APSCs fabricated by blending P1 , P2 and P3 with donor polymers PM5 and PM6 exhibit modest power conversion efficiencies (PCEs), with the champion P2 ‐based APSC achieving PCE=5.64 %. Detailed morphological and microstructural analysis by AFM and GIWAXS reveal a non‐optimal APSC active layer morphology, which suppresses charge transport. Despite the modest efficiencies, these APSCs demonstrate the feasibility of using ADT as a scalable and inexpensive electron rich/donor building block for APSCs.
- Authors:
-
- Department of Chemistry and INSTM Research Unit University of Pavia Viale Taramelli 12 27100 Pavia Italy, Department of Chemistry Center for Light Energy-Activated Redox Processes and the Materials Research Center Northwestern University 2145 Sheridan Road 60208 Evanston Illinois USA
- Department of Chemistry Center for Light Energy-Activated Redox Processes and the Materials Research Center Northwestern University 2145 Sheridan Road 60208 Evanston Illinois USA
- Department of Chemistry and INSTM Research Unit University of Pavia Viale Taramelli 12 27100 Pavia Italy
- School of Energy and Chemical Engineering Perovtronics Research Center Low Dimensional Carbon Materials Center Ulsan National Institute of Science and Technology (UNIST) 50 UNIST-gil, Ulju-gun 44919 Ulsan South Korea
- School of Energy and Chemical Engineering Perovtronics Research Center Low Dimensional Carbon Materials Center Ulsan National Institute of Science and Technology (UNIST) 50 UNIST-gil, Ulju-gun 44919 Ulsan South Korea, Graduate School of Carbon Neutrality Ulsan National Institute of Science and Technology (UNIST) 50 UNIST-gil, Ulju-gun 44919 Ulsan South Korea
- Department of Chemistry Center for Light Energy-Activated Redox Processes and the Materials Research Center Northwestern University 2145 Sheridan Road 60208 Evanston Illinois USA, School of Materials Science and Engineering Georgia Institute of Technology 771 Ferst Drive 30332 Atlanta Georgia USA
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1994566
- Grant/Contract Number:
- AC02-05CH11231; AC02-06CH11357
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Chemistry - A European Journal
- Additional Journal Information:
- Journal Name: Chemistry - A European Journal Journal Volume: 29 Journal Issue: 45; Journal ID: ISSN 0947-6539
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Forti, Giacomo, Pankow, Robert M., Qin, Fei, Cho, Yongjoon, Kerwin, Brendan, Duplessis, Isaiah, Nitti, Andrea, Jeong, Seonghun, Yang, Changduk, Facchetti, Antonio, Pasini, Dario, and Marks, Tobin J. Anthradithiophene (ADT)‐Based Polymerized Non‐Fullerene Acceptors for All‐Polymer Solar Cells. Germany: N. p., 2023.
Web. doi:10.1002/chem.202300653.
Forti, Giacomo, Pankow, Robert M., Qin, Fei, Cho, Yongjoon, Kerwin, Brendan, Duplessis, Isaiah, Nitti, Andrea, Jeong, Seonghun, Yang, Changduk, Facchetti, Antonio, Pasini, Dario, & Marks, Tobin J. Anthradithiophene (ADT)‐Based Polymerized Non‐Fullerene Acceptors for All‐Polymer Solar Cells. Germany. https://doi.org/10.1002/chem.202300653
Forti, Giacomo, Pankow, Robert M., Qin, Fei, Cho, Yongjoon, Kerwin, Brendan, Duplessis, Isaiah, Nitti, Andrea, Jeong, Seonghun, Yang, Changduk, Facchetti, Antonio, Pasini, Dario, and Marks, Tobin J. Tue .
"Anthradithiophene (ADT)‐Based Polymerized Non‐Fullerene Acceptors for All‐Polymer Solar Cells". Germany. https://doi.org/10.1002/chem.202300653.
@article{osti_1994566,
title = {Anthradithiophene (ADT)‐Based Polymerized Non‐Fullerene Acceptors for All‐Polymer Solar Cells},
author = {Forti, Giacomo and Pankow, Robert M. and Qin, Fei and Cho, Yongjoon and Kerwin, Brendan and Duplessis, Isaiah and Nitti, Andrea and Jeong, Seonghun and Yang, Changduk and Facchetti, Antonio and Pasini, Dario and Marks, Tobin J.},
abstractNote = {Abstract Realizing efficient all‐polymer solar cell (APSC) acceptors typically involves increased building block synthetic complexity, hence potentially unscalable syntheses and/or prohibitive costs. Here we report the synthesis, characterization, and implementation in APSCs of three new polymer acceptors P1 – P3 using a scalable donor fragment, bis(2‐octyldodecyl)anthra[1,2‐b : 5,6‐b’]dithiophene‐4,10‐dicarboxylate ( ADT ) co‐polymerized with the high‐efficiency acceptor units, NDI, Y6, and IDIC. All three copolymers have comparable photophysics to known polymers; however, APSCs fabricated by blending P1 , P2 and P3 with donor polymers PM5 and PM6 exhibit modest power conversion efficiencies (PCEs), with the champion P2 ‐based APSC achieving PCE=5.64 %. Detailed morphological and microstructural analysis by AFM and GIWAXS reveal a non‐optimal APSC active layer morphology, which suppresses charge transport. Despite the modest efficiencies, these APSCs demonstrate the feasibility of using ADT as a scalable and inexpensive electron rich/donor building block for APSCs.},
doi = {10.1002/chem.202300653},
journal = {Chemistry - A European Journal},
number = 45,
volume = 29,
place = {Germany},
year = {Tue Jul 18 00:00:00 EDT 2023},
month = {Tue Jul 18 00:00:00 EDT 2023}
}
Works referenced in this record:
All-Polymer Solar Cell Performance Optimized via Systematic Molecular Weight Tuning of Both Donor and Acceptor Polymers
journal, January 2016
- Zhou, Nanjia; Dudnik, Alexander S.; Li, Ting I. N. G.
- Journal of the American Chemical Society, Vol. 138, Issue 4
A high-mobility electron-transporting polymer for printed transistors
journal, January 2009
- Yan, He; Chen, Zhihua; Zheng, Yan
- Nature, Vol. 457, Issue 7230, p. 679-686
Definition of green synthetic tools based on safer reaction media, heterogeneous catalysis, and flow technology
journal, January 2018
- Vaccaro, Luigi; Curini, Massimo; Ferlin, Francesco
- Pure and Applied Chemistry, Vol. 90, Issue 1
Systematic Merging of Nonfullerene Acceptor π-Extension and Tetrafluorination Strategies Affords Polymer Solar Cells with >16% Efficiency
journal, April 2021
- Li, Guoping; Zhang, Xiaohua; Jones, Leighton O.
- Journal of the American Chemical Society, Vol. 143, Issue 16
Scalable Synthesis of Naphthothiophene-based D-π-D Extended Oligomers through Cascade Direct Arylation Processes
journal, November 2018
- Pasini, Dario; Nitti, Andrea; Osw, Peshawa
- Synlett, Vol. 29, Issue 19
An Anthradithiophene Donor Polymer for Organic Solar Cells with a Good Balance between Efficiency and Synthetic Accessibility
journal, October 2022
- Bianchi, Gabriele; Carbonera, Chiara; Ciammaruchi, Laura
- Solar RRL, Vol. 6, Issue 12
Anthradithiophene-based organic semiconductors through regiodirected double annulations
journal, January 2021
- Nitti, Andrea; Forti, Giacomo; Bianchi, Gabriele
- Journal of Materials Chemistry C, Vol. 9, Issue 29
Polymer Solar Cells with 18.74% Efficiency: From Bulk Heterojunction to Interdigitated Bulk Heterojunction
journal, October 2021
- Xu, Xiaopeng; Yu, Liyang; Meng, Huifeng
- Advanced Functional Materials, Vol. 32, Issue 4
Mixed-flow design for microfluidic printing of two-component polymer semiconductor systems
journal, July 2020
- Wang, Gang; Feng, Liang-Wen; Huang, Wei
- Proceedings of the National Academy of Sciences, Vol. 117, Issue 30
Advances in Green-Solvent-Processable All-Polymer Solar Cells
journal, June 2022
- Bai, Qingqing; Sun, Huiliang; Guo, Xugang
- Chinese Journal of Polymer Science, Vol. 40, Issue 8
Blending Donors with Different Molecular Weights: An Efficient Strategy to Resolve the Conflict between Coherence Length and Intermixed Phase in Polymer/Nonfullerene Solar Cells
journal, November 2021
- Liang, Qiuju; Hu, Zhangbo; Yao, Jianhong
- Small, Vol. 18, Issue 3
A Narrow‐Bandgap n‐Type Polymer with an Acceptor–Acceptor Backbone Enabling Efficient All‐Polymer Solar Cells
journal, September 2020
- Sun, Huiliang; Yu, Han; Shi, Yongqiang
- Advanced Materials, Vol. 32, Issue 43
Synergistic Effect of Fluorination on Molecular Energy Level Modulation in Highly Efficient Photovoltaic Polymers
journal, November 2013
- Zhang, Maojie; Guo, Xia; Zhang, Shaoqing
- Advanced Materials, Vol. 26, Issue 7
Configurational Isomers Induced Significant Difference in All‐Polymer Solar Cells
journal, April 2021
- Wang, Hengtao; Chen, Hui; Xie, Weicheng
- Advanced Functional Materials, Vol. 31, Issue 26
A review of non-fullerene polymer solar cells: from device physics to morphology control
journal, February 2019
- Gurney, Robert S.; Lidzey, David G.; Wang, Tao
- Reports on Progress in Physics, Vol. 82, Issue 3
A Difluoro‐Monobromo End Group Enables High‐Performance Polymer Acceptor and Efficient All‐Polymer Solar Cells Processable with Green Solvent under Ambient Condition
journal, May 2021
- Yu, Han; Luo, Siwei; Sun, Rui
- Advanced Functional Materials, Vol. 31, Issue 25
11.2% Efficiency all-polymer solar cells with high open-circuit voltage
journal, April 2019
- Meng, Yuan; Wu, Jingnan; Guo, Xia
- Science China Chemistry, Vol. 62, Issue 7
The atom economy--a search for synthetic efficiency
journal, December 1991
- Trost, B.
- Science, Vol. 254, Issue 5037
Beyond efficiency: scalability of molecular donor materials for organic photovoltaics
journal, January 2016
- Po, Riccardo; Roncali, Jean
- Journal of Materials Chemistry C, Vol. 4, Issue 17
Domino Direct Arylation and Cross-Aldol for Rapid Construction of Extended Polycyclic π-Scaffolds
journal, June 2017
- Nitti, Andrea; Bianchi, Gabriele; Po, Riccardo
- Journal of the American Chemical Society, Vol. 139, Issue 26
Simulation of charge Carrier mobility unbalance in organic solar cells
journal, August 2018
- Gagliardi, Alessio; Wang, Shengda; Albes, Tim
- Organic Electronics, Vol. 59
Achieving highly efficient all-polymer solar cells by green-solvent-processing under ambient atmosphere
journal, January 2021
- Liu, Bin; Sun, Huiliang; Lee, Jin-Woo
- Energy & Environmental Science
10.13% Efficiency All‐Polymer Solar Cells Enabled by Improving the Optical Absorption of Polymer Acceptors
journal, April 2020
- Fan, Qunping; Ma, Ruijie; Liu, Tao
- Solar RRL, Vol. 4, Issue 6
Non-fullerene acceptors with direct and indirect hexa-fluorination afford >17% efficiency in polymer solar cells
journal, January 2022
- Li, Guoping; Feng, Liang-Wen; Mukherjee, Subhrangsu
- Energy & Environmental Science, Vol. 15, Issue 2
Constructing a Strongly Absorbing Low-Bandgap Polymer Acceptor for High-Performance All-Polymer Solar Cells
journal, September 2017
- Zhang, Zhi-Guo; Yang, Yankang; Yao, Jia
- Angewandte Chemie International Edition, Vol. 56, Issue 43
Electron Barrier Formation at the Organic-Back Contact Interface is the First Step in Thermal Degradation of Polymer Solar Cells
journal, March 2014
- Sachs-Quintana, I. T.; Heumüller, Thomas; Mateker, William R.
- Advanced Functional Materials, Vol. 24, Issue 25
π-Extension and chlorination of non-fullerene acceptors enable more readily processable and sustainable high-performance organic solar cells
journal, April 2023
- Su, Ning; Chen, Jianhua; Peng, Mengran
- Journal of Energy Chemistry, Vol. 79
Green Chemistry: Principles and Practice
journal, January 2010
- Anastas, Paul; Eghbali, Nicolas
- Chem. Soc. Rev., Vol. 39, Issue 1
All-Polymer Solar Cells: Recent Progress, Challenges, and Prospects
journal, February 2019
- Wang, Gang; Melkonyan, Ferdinand S.; Facchetti, Antonio
- Angewandte Chemie International Edition, Vol. 58, Issue 13
High-Efficiency All-Polymer Solar Cells with Poly-Small-Molecule Acceptors Having π-Extended Units with Broad Near-IR Absorption
journal, January 2021
- Su, Ning; Ma, Ruijie; Li, Guoping
- ACS Energy Letters, Vol. 6, Issue 2
16.52% Efficiency All‐Polymer Solar Cells with High Tolerance of the Photoactive Layer Thickness
journal, April 2022
- Zhang, Wenqing; Sun, Chenkai; Angunawela, Indunil
- Advanced Materials, Vol. 34, Issue 20
One-Pot Regiodirected Annulations for the Rapid Synthesis of π-Extended Oligomers
journal, April 2020
- Nitti, Andrea; Osw, Peshawa; Calcagno, Giuseppe
- Organic Letters, Vol. 22, Issue 8
High-Performance n-Type Polymer Semiconductors: Applications, Recent Development, and Challenges
journal, June 2020
- Sun, Huiliang; Guo, Xugang; Facchetti, Antonio
- Chem, Vol. 6, Issue 6
Non-Fullerene Electron Acceptors for Use in Organic Solar Cells
journal, October 2015
- Nielsen, Christian B.; Holliday, Sarah; Chen, Hung-Yang
- Accounts of Chemical Research, Vol. 48, Issue 11
Determining the Role of Polymer Molecular Weight for High-Performance All-Polymer Solar Cells: Its Effect on Polymer Aggregation and Phase Separation
journal, February 2015
- Kang, Hyunbum; Uddin, Mohammad Afsar; Lee, Changyeon
- Journal of the American Chemical Society, Vol. 137, Issue 6
Breath figure–derived porous semiconducting films for organic electronics
journal, March 2020
- Zhang, Xinan; Wang, Binghao; Huang, Lizhen
- Science Advances, Vol. 6, Issue 13
16.7%-efficiency ternary blended organic photovoltaic cells with PCBM as the acceptor additive to increase the open-circuit voltage and phase purity
journal, January 2019
- Pan, Ming-Ao; Lau, Tsz-Ki; Tang, Yabing
- Journal of Materials Chemistry A, Vol. 7, Issue 36
Simultaneous Substitution of Silicon and Fluorine Atom on Donor-Acceptor Copolymers for Photovoltaic Applications
journal, January 2017
- Huang, Shang-Cyuan; Yang, Chien-Hsin; Chuang, Yao-Yuan
- Macromolecular Chemistry and Physics, Vol. 218, Issue 7
Building Blocks for High‐Efficiency Organic Photovoltaics: Interplay of Molecular, Crystal, and Electronic Properties in Post‐Fullerene ITIC Ensembles
journal, September 2019
- Swick, Steven M.; Gebraad, Tim; Jones, Leighton
- ChemPhysChem, Vol. 20, Issue 20
High-performance wide-bandgap copolymers based on indacenodithiophene and indacenodithieno[3,2-b]thiophene units
journal, January 2017
- Cai, Yunhao; Zhang, Xiaolong; Xue, Xiaonan
- Journal of Materials Chemistry C, Vol. 5, Issue 31
Scalable Synthesis of Naphthothiophene and Benzodithiophene Scaffolds as π-Conjugated Synthons for Organic Materials
journal, December 2018
- Nitti, Andrea; Pasini, Dario; Bianchi, Gabriele
- Synthesis, Vol. 51, Issue 03
Origin of the fill factor loss in bulk-heterojunction organic solar cells
journal, April 2014
- Wu, Lili; Zang, Huidong; Hsiao, Yu-Che
- Applied Physics Letters, Vol. 104, Issue 15
Manipulating Aggregation and Molecular Orientation in All-Polymer Photovoltaic Cells
journal, August 2015
- Ye, Long; Jiao, Xuechen; Zhou, Meng
- Advanced Materials, Vol. 27, Issue 39
Fluorinating π‐Extended Molecular Acceptors Yields Highly Connected Crystal Structures and Low Reorganization Energies for Efficient Solar Cells
journal, May 2020
- Swick, Steven M.; Alzola, Joaquin M.; Sangwan, Vinod K.
- Advanced Energy Materials, Vol. 10, Issue 23
The effect of carrier mobility in organic solar cells
journal, April 2010
- Shieh, Ji-Ting; Liu, Chiou-Hua; Meng, Hsin-Fei
- Journal of Applied Physics, Vol. 107, Issue 8
Photophysics of Molecular-Weight-Induced Losses in Indacenodithienothiophene-Based Solar Cells
journal, June 2015
- Gasparini, Nicola; Katsouras, Athanasios; Prodromidis, Mamantos I.
- Advanced Functional Materials, Vol. 25, Issue 30
Balanced Electric Field Dependent Mobilities: A Key to Access High Fill Factors in Organic Bulk Heterojunction Solar Cells
journal, February 2018
- Yin, Hang; Bi, Pengqing; Cheung, Sin Hang
- Solar RRL, Vol. 2, Issue 4
Recent Advances in n‐Type Polymers for All‐Polymer Solar Cells
journal, February 2019
- Genene, Zewdneh; Mammo, Wendimagegn; Wang, Ergang
- Advanced Materials, Vol. 31, Issue 22
Bithiopheneimide–Dithienosilole/Dithienogermole Copolymers for Efficient Solar Cells: Information from Structure–Property–Device Performance Correlations and Comparison to Thieno[3,4- c ]pyrrole-4,6-dione Analogues
journal, October 2012
- Guo, Xugang; Zhou, Nanjia; Lou, Sylvia J.
- Journal of the American Chemical Society, Vol. 134, Issue 44
Polymer acceptors for all-polymer solar cells
journal, August 2021
- Ji, Xiaofei; Xiao, Zuo; Sun, Huiliang
- Journal of Semiconductors, Vol. 42, Issue 8
All-Polymer Solar Cells Approaching 12% Efficiency with a New π-Conjugated Polymer Donor Enabled by a Nonhalogenated Solvent Process
journal, June 2021
- Gokulnath, Thavamani; Choi, Jungmin; Jin, Hyunjung
- ACS Applied Materials & Interfaces, Vol. 13, Issue 24
Multi‐Selenophene‐Containing Narrow Bandgap Polymer Acceptors for All‐Polymer Solar Cells with over 15 % Efficiency and High Reproducibility
journal, June 2021
- Fan, Qunping; Fu, Huiting; Wu, Qiang
- Angewandte Chemie International Edition, Vol. 60, Issue 29
E factors, green chemistry and catalysis: an odyssey
journal, January 2008
- Sheldon, Roger A.
- Chemical Communications, Issue 29
Rational Design of High-Performance Wide-Bandgap (≈2 eV) Polymer Semiconductors as Electron Donors in Organic Photovoltaics Exhibiting High Open Circuit Voltages (≈1 V)
journal, December 2016
- Chochos, Christos L.; Katsouras, Athanasios; Gasparini, Nicola
- Macromolecular Rapid Communications, Vol. 38, Issue 2
Low-Bandgap n-Type Polymer Based on a Fused-DAD-Type Heptacyclic Ring for All-Polymer Solar Cell Application with a Power Conversion Efficiency of 10.7%
journal, April 2020
- Tang, Ailing; Li, Jianfeng; Zhang, Bao
- ACS Macro Letters, Vol. 9, Issue 5
π‐Extended Conjugated Polymer Acceptor Containing Thienylene–Vinylene–Thienylene Unit for High‐Performance Thick‐Film All‐Polymer Solar Cells with Superior Long‐Term Stability
journal, November 2021
- Zhang, Jiabin; Tan, Ching‐Hong; Zhang, Kai
- Advanced Energy Materials, Vol. 11, Issue 48
Mechanically Robust All-Polymer Solar Cells from Narrow Band Gap Acceptors with Hetero-Bridging Atoms
journal, March 2020
- Fan, Qunping; Su, Wenyan; Chen, Shanshan
- Joule, Vol. 4, Issue 3
14.4% efficiency all-polymer solar cell with broad absorption and low energy loss enabled by a novel polymer acceptor
journal, June 2020
- Jia, Tao; Zhang, Jiabin; Zhong, Wenkai
- Nano Energy, Vol. 72
Polymerized small molecular acceptor based all-polymer solar cells with an efficiency of 16.16% via tuning polymer blend morphology by molecular design
journal, September 2021
- Du, Jiaqi; Hu, Ke; Zhang, Jinyuan
- Nature Communications, Vol. 12, Issue 1
From lab to fab: how must the polymer solar cell materials design change? – an industrial perspective
journal, January 2014
- Po, Riccardo; Bernardi, Andrea; Calabrese, Anna
- Energy & Environmental Science, Vol. 7, Issue 3