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Title: 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:
 [1];  [2];  [2];  [2];  [2];  [2];  [3];  [4];  [5];  [6];  [3]; ORCiD logo [2]
  1. 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
  2. Department of Chemistry Center for Light Energy-Activated Redox Processes and the Materials Research Center Northwestern University 2145 Sheridan Road 60208 Evanston Illinois USA
  3. Department of Chemistry and INSTM Research Unit University of Pavia Viale Taramelli 12 27100 Pavia Italy
  4. 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
  5. 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
  6. 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}
}

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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
  • DOI: 10.1021/jacs.5b10735

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
  • DOI: 10.1038/nature07727

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
  • DOI: 10.1515/pac-2017-0409

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
  • DOI: 10.1021/jacs.1c00211

Scalable Synthesis of Naphthothiophene-based D-π-D Extended Oligomers through Cascade Direct Arylation Processes
journal, November 2018


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
  • DOI: 10.1002/solr.202200643

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
  • DOI: 10.1039/D1TC01887F

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
  • DOI: 10.1002/adfm.202108797

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
  • DOI: 10.1073/pnas.2000398117

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
  • DOI: 10.1007/s10118-022-2772-7

A Narrow‐Bandgap n‐Type Polymer with an Acceptor–Acceptor Backbone Enabling Efficient All‐Polymer Solar Cells
journal, September 2020


Synergistic Effect of Fluorination on Molecular Energy Level Modulation in Highly Efficient Photovoltaic Polymers
journal, November 2013


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
  • DOI: 10.1002/adfm.202100877

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
  • DOI: 10.1088/1361-6633/ab0530

11.2% Efficiency all-polymer solar cells with high open-circuit voltage
journal, April 2019


The atom economy--a search for synthetic efficiency
journal, December 1991


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
  • DOI: 10.1039/C5TC03740A

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
  • DOI: 10.1021/jacs.7b03412

Simulation of charge Carrier mobility unbalance in organic solar cells
journal, August 2018


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
  • DOI: 10.1039/D1EE01310F

10.13% Efficiency All‐Polymer Solar Cells Enabled by Improving the Optical Absorption of Polymer Acceptors
journal, April 2020


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
  • DOI: 10.1039/D1EE03225A

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
  • DOI: 10.1002/anie.201707678

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
  • DOI: 10.1002/adfm.201304166

Green Chemistry: Principles and Practice
journal, January 2010

  • Anastas, Paul; Eghbali, Nicolas
  • Chem. Soc. Rev., Vol. 39, Issue 1
  • DOI: 10.1039/B918763B

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
  • DOI: 10.1002/anie.201808976

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
  • DOI: 10.1002/adma.202108749

One-Pot Regiodirected Annulations for the Rapid Synthesis of π-Extended Oligomers
journal, April 2020


High-Performance n-Type Polymer Semiconductors: Applications, Recent Development, and Challenges
journal, June 2020


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
  • DOI: 10.1021/acs.accounts.5b00199

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
  • DOI: 10.1021/ja5123182

Breath figure–derived porous semiconducting films for organic electronics
journal, March 2020


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
  • DOI: 10.1039/C9TA06929A

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
  • DOI: 10.1002/macp.201600410

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
  • DOI: 10.1039/C7TC01909B

Scalable Synthesis of Naphthothiophene and Benzodithiophene Scaffolds as π-Conjugated Synthons for Organic Materials
journal, December 2018


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
  • DOI: 10.1063/1.4871582

Manipulating Aggregation and Molecular Orientation in All-Polymer Photovoltaic Cells
journal, August 2015


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
  • DOI: 10.1002/aenm.202000635

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
  • DOI: 10.1063/1.3327210

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
  • DOI: 10.1002/adfm.201501062

Balanced Electric Field Dependent Mobilities: A Key to Access High Fill Factors in Organic Bulk Heterojunction Solar Cells
journal, February 2018


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
  • DOI: 10.1002/adma.201807275

Polymer acceptors for all-polymer solar cells
journal, August 2021


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
  • DOI: 10.1021/acsami.1c05921

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
  • DOI: 10.1002/anie.202101577

E factors, green chemistry and catalysis: an odyssey
journal, January 2008


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
  • DOI: 10.1002/marc.201600614

Mechanically Robust All-Polymer Solar Cells from Narrow Band Gap Acceptors with Hetero-Bridging Atoms
journal, March 2020


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
  • DOI: 10.1039/c3ee43460e