n ‐Type Rigid Semiconducting Polymers Bearing Oligo(Ethylene Glycol) Side Chains for High‐Performance Organic Electrochemical Transistors
Abstract
Abstract N‐type conjugated polymers as the semiconducting component of organic electrochemical transistors (OECTs) are still undeveloped with respect to their p‐type counterparts. Herein, we report two rigid n‐type conjugated polymers bearing oligo(ethylene glycol) (OEG) side chains, PgNaN and PgNgN, which demonstrated an essentially torsion‐free π‐conjugated backbone. The planarity and electron‐deficient rigid structures enable the resulting polymers to achieve high electron mobility in an OECT device of up to the 10 −3 cm 2 V −1 s −1 range, with a deep‐lying LUMO energy level lower than −4.0 eV. Prominently, the polymers exhibited a high device performance with a maximum dimensionally normalized transconductance of 0.212 S cm −1 and the product of charge‐carrier mobility μ and volumetric capacitance C* of 0.662±0.113 F cm −1 V −1 s −1 , which are among the highest in n‐type conjugated polymers reported to date. Moreover, the polymers are synthesized via a metal‐free aldol‐condensation polymerization, which is beneficial to their application in bioelectronics.
- Authors:
-
- Department of Physical Science and Engineering Division King Abdullah University of Science and Technology (KAUST) Thuwal 23955-6900 Saudi Arabia
- Department of Chemistry and Centre for Plastic Electronics Imperial College London London W12 0BZ UK
- Department of Biomedical Engineering Northwestern University 2145 Sheridan Rd Evanston IL 60208 USA
- Department of Chemistry Northwestern University 2145 Sheridan Rd Evanston IL 60208 USA
- Department of Biomedical Engineering Northwestern University 2145 Sheridan Rd Evanston IL 60208 USA, Simpson Querrey Institute Northwestern University Chicago IL 60611 USA
- Department of Physical Science and Engineering Division King Abdullah University of Science and Technology (KAUST) Thuwal 23955-6900 Saudi Arabia, Department of Chemistry and Centre for Plastic Electronics Imperial College London London W12 0BZ UK, Department of Chemistry Chemistry Research Laboratory University of Oxford Oxford OX1 3TA UK
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1776419
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition) Journal Volume: 60 Journal Issue: 17; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Chen, Xingxing, Marks, Adam, Paulsen, Bryan D., Wu, Ruiheng, Rashid, Reem B., Chen, Hu, Alsufyani, Maryam, Rivnay, Jonathan, and McCulloch, Iain. n ‐Type Rigid Semiconducting Polymers Bearing Oligo(Ethylene Glycol) Side Chains for High‐Performance Organic Electrochemical Transistors. Germany: N. p., 2021.
Web. doi:10.1002/anie.202013998.
Chen, Xingxing, Marks, Adam, Paulsen, Bryan D., Wu, Ruiheng, Rashid, Reem B., Chen, Hu, Alsufyani, Maryam, Rivnay, Jonathan, & McCulloch, Iain. n ‐Type Rigid Semiconducting Polymers Bearing Oligo(Ethylene Glycol) Side Chains for High‐Performance Organic Electrochemical Transistors. Germany. https://doi.org/10.1002/anie.202013998
Chen, Xingxing, Marks, Adam, Paulsen, Bryan D., Wu, Ruiheng, Rashid, Reem B., Chen, Hu, Alsufyani, Maryam, Rivnay, Jonathan, and McCulloch, Iain. Fri .
"n ‐Type Rigid Semiconducting Polymers Bearing Oligo(Ethylene Glycol) Side Chains for High‐Performance Organic Electrochemical Transistors". Germany. https://doi.org/10.1002/anie.202013998.
@article{osti_1776419,
title = {n ‐Type Rigid Semiconducting Polymers Bearing Oligo(Ethylene Glycol) Side Chains for High‐Performance Organic Electrochemical Transistors},
author = {Chen, Xingxing and Marks, Adam and Paulsen, Bryan D. and Wu, Ruiheng and Rashid, Reem B. and Chen, Hu and Alsufyani, Maryam and Rivnay, Jonathan and McCulloch, Iain},
abstractNote = {Abstract N‐type conjugated polymers as the semiconducting component of organic electrochemical transistors (OECTs) are still undeveloped with respect to their p‐type counterparts. Herein, we report two rigid n‐type conjugated polymers bearing oligo(ethylene glycol) (OEG) side chains, PgNaN and PgNgN, which demonstrated an essentially torsion‐free π‐conjugated backbone. The planarity and electron‐deficient rigid structures enable the resulting polymers to achieve high electron mobility in an OECT device of up to the 10 −3 cm 2 V −1 s −1 range, with a deep‐lying LUMO energy level lower than −4.0 eV. Prominently, the polymers exhibited a high device performance with a maximum dimensionally normalized transconductance of 0.212 S cm −1 and the product of charge‐carrier mobility μ and volumetric capacitance C* of 0.662±0.113 F cm −1 V −1 s −1 , which are among the highest in n‐type conjugated polymers reported to date. Moreover, the polymers are synthesized via a metal‐free aldol‐condensation polymerization, which is beneficial to their application in bioelectronics.},
doi = {10.1002/anie.202013998},
journal = {Angewandte Chemie (International Edition)},
number = 17,
volume = 60,
place = {Germany},
year = {Fri Mar 12 00:00:00 EST 2021},
month = {Fri Mar 12 00:00:00 EST 2021}
}
https://doi.org/10.1002/anie.202013998
Works referenced in this record:
Impact of ring torsion on the intrachain mobility in conjugated polymers
journal, March 2007
- Hultell, Magnus; Stafström, Sven
- Physical Review B, Vol. 75, Issue 10
Lactate Detection in Tumor Cell Cultures Using Organic Transistor Circuits
journal, January 2017
- Braendlein, Marcel; Pappa, Anna-Maria; Ferro, Marc
- Advanced Materials, Vol. 29, Issue 13
π-Building Blocks for Organic Electronics: Revaluation of “Inductive” and “Resonance” Effects of π-Electron Deficient Units
journal, September 2013
- Takimiya, Kazuo; Osaka, Itaru; Nakano, Masahiro
- Chemistry of Materials, Vol. 26, Issue 1
Diketopyrrolopyrrole-based Conjugated Polymers Bearing Branched Oligo(Ethylene Glycol) Side Chains for Photovoltaic Devices
journal, June 2016
- Chen, Xingxing; Zhang, Zijian; Ding, Zicheng
- Angewandte Chemie, Vol. 128, Issue 35
Insight into High-Performance Conjugated Polymers for Organic Field-Effect Transistors
journal, December 2018
- Yang, Jie; Zhao, Zhiyuan; Wang, Shuai
- Chem, Vol. 4, Issue 12
Recent Progress in High-Mobility Organic Transistors: A Reality Check
journal, July 2018
- Paterson, Alexandra F.; Singh, Saumya; Fallon, Kealan J.
- Advanced Materials, Vol. 30, Issue 36
Ultimately Sensitive Organic Bioelectronic Transistor Sensors by Materials and Device Structure Design
journal, September 2019
- Picca, Rosaria Anna; Manoli, Kyriaki; Macchia, Eleonora
- Advanced Functional Materials, Vol. 30, Issue 20
High-Performance Organic Electrochemical Transistors Based on Conjugated Polyelectrolyte Copolymers
journal, June 2019
- Schmode, Philip; Ohayon, David; Reichstein, Paul M.
- Chemistry of Materials, Vol. 31, Issue 14
Biofuel powered glucose detection in bodily fluids with an n-type conjugated polymer
journal, December 2019
- Ohayon, David; Nikiforidis, Georgios; Savva, Achilleas
- Nature Materials, Vol. 19, Issue 4
Active Materials for Organic Electrochemical Transistors
journal, July 2018
- Zeglio, Erica; Inganäs, Olle
- Advanced Materials, Vol. 30, Issue 44
Ethylene Glycol-Based Side Chain Length Engineering in Polythiophenes and its Impact on Organic Electrochemical Transistor Performance
journal, July 2020
- Moser, Maximilian; Savagian, Lisa R.; Savva, Achilleas
- Chemistry of Materials, Vol. 32, Issue 15
Redox-Stability of Alkoxy-BDT Copolymers and their Use for Organic Bioelectronic Devices
journal, February 2018
- Giovannitti, Alexander; Thorley, Karl J.; Nielsen, Christian B.
- Advanced Functional Materials, Vol. 28, Issue 17
Finding the equilibrium of organic electrochemical transistors
journal, May 2020
- Kaphle, Vikash; Paudel, Pushpa Raj; Dahal, Drona
- Nature Communications, Vol. 11, Issue 1
High-Molecular-Weight Regular Alternating Diketopyrrolopyrrole-based Terpolymers for Efficient Organic Solar Cells
journal, June 2013
- Hendriks, Koen H.; Heintges, Gaël H. L.; Gevaerts, Veronique S.
- Angewandte Chemie International Edition, Vol. 52, Issue 32
n-Type organic electrochemical transistors: materials and challenges
journal, January 2018
- Sun, Hengda; Gerasimov, Jennifer; Berggren, Magnus
- Journal of Materials Chemistry C, Vol. 6, Issue 44
Semiconductors for organic transistors
journal, March 2007
- Facchetti, Antonio
- Materials Today, Vol. 10, Issue 3
Diketopyrrolopyrrole-based Conjugated Polymers Bearing Branched Oligo(Ethylene Glycol) Side Chains for Photovoltaic Devices
journal, June 2016
- Chen, Xingxing; Zhang, Zijian; Ding, Zicheng
- Angewandte Chemie International Edition, Vol. 55, Issue 35
Contact Resistance Effects in Highly Doped Organic Electrochemical Transistors
journal, August 2016
- Kaphle, Vikash; Liu, Shiyi; Al-Shadeedi, Akram
- Advanced Materials, Vol. 28, Issue 39
Electronic polymers in lipid membranes
journal, June 2015
- Johansson, Patrik K.; Jullesson, David; Elfwing, Anders
- Scientific Reports, Vol. 5, Issue 1
Organic Bioelectronics
journal, September 2007
- Berggren, M.; Richter-Dahlfors, A.
- Advanced Materials, Vol. 19, Issue 20
Influence of disorder on transfer characteristics of organic electrochemical transistors
journal, July 2017
- Friedlein, Jacob T.; Rivnay, Jonathan; Dunlap, David H.
- Applied Physics Letters, Vol. 111, Issue 2
High-sensitivity ion detection at low voltages with current-driven organic electrochemical transistors
journal, April 2018
- Ghittorelli, Matteo; Lingstedt, Leona; Romele, Paolo
- Nature Communications, Vol. 9, Issue 1
Replacing Alkyl with Oligo(ethylene glycol) as Side Chains of Conjugated Polymers for Close π–π Stacking
journal, June 2015
- Meng, Bin; Song, Haiyang; Chen, Xingxing
- Macromolecules, Vol. 48, Issue 13
Complementary Logic Circuits Based on High-Performance n-Type Organic Electrochemical Transistors
journal, January 2018
- Sun, Hengda; Vagin, Mikhail; Wang, Suhao
- Advanced Materials, Vol. 30, Issue 9
Molecular Design of Semiconducting Polymers for High-Performance Organic Electrochemical Transistors
journal, August 2016
- Nielsen, Christian B.; Giovannitti, Alexander; Sbircea, Dan-Tiberiu
- Journal of the American Chemical Society, Vol. 138, Issue 32
Recent progress in the development of n-type organic semiconductors for organic field effect transistors
journal, January 2017
- Quinn, Jesse T. E.; Zhu, Jiaxin; Li, Xu
- Journal of Materials Chemistry C, Vol. 5, Issue 34
The role of chemical design in the performance of organic semiconductors
journal, January 2020
- Bronstein, Hugo; Nielsen, Christian B.; Schroeder, Bob C.
- Nature Reviews Chemistry, Vol. 4, Issue 2
Hybrid Alkyl–Ethylene Glycol Side Chains Enhance Substrate Adhesion and Operational Stability in Accumulation Mode Organic Electrochemical Transistors
journal, November 2019
- Wang, Yazhou; Zeglio, Erica; Liao, Hailiang
- Chemistry of Materials, Vol. 31, Issue 23
25th Anniversary Article: Organic Field-Effect Transistors: The Path Beyond Amorphous Silicon
journal, January 2014
- Sirringhaus, Henning
- Advanced Materials, Vol. 26, Issue 9
Ionic-Liquid Doping Enables High Transconductance, Fast Response Time, and High Ion Sensitivity in Organic Electrochemical Transistors
journal, November 2018
- Wu, Xihu; Surendran, Abhijith; Ko, Jieun
- Advanced Materials, Vol. 31, Issue 2
Ionic-to-electronic coupling efficiency in PEDOT:PSS films operated in aqueous electrolytes
journal, January 2018
- Savva, Achilleas; Wustoni, Shofarul; Inal, Sahika
- Journal of Materials Chemistry C, Vol. 6, Issue 44
Organic mixed ionic–electronic conductors
journal, August 2019
- Paulsen, Bryan D.; Tybrandt, Klas; Stavrinidou, Eleni
- Nature Materials, Vol. 19, Issue 1
Materials in Organic Electrochemical Transistors for Bioelectronic Applications: Past, Present, and Future
journal, December 2018
- Moser, Maximilian; Ponder, James F.; Wadsworth, Andrew
- Advanced Functional Materials, Vol. 29, Issue 21
A polymer electron donor based on isoindigo units bearing branched oligo(ethylene glycol) side chains for polymer solar cells
journal, January 2017
- Chen, Xingxing; Zhang, Zijian; Liu, Jun
- Polymer Chemistry, Vol. 8, Issue 36
Organic electrochemical transistors
journal, January 2018
- Rivnay, Jonathan; Inal, Sahika; Salleo, Alberto
- Nature Reviews Materials, Vol. 3, Issue 2
Influence of Side-Chain Chemistry on Structure and Ionic Conduction Characteristics of Polythiophene Derivatives: A Computational and Experimental Study
journal, February 2019
- Dong, Ban Xuan; Nowak, Christian; Onorato, Jonathan W.
- Chemistry of Materials, Vol. 31, Issue 4
Non-fullerene acceptors for organic solar cells
journal, February 2018
- Yan, Cenqi; Barlow, Stephen; Wang, Zhaohui
- Nature Reviews Materials, Vol. 3, Issue 3
N-type organic electrochemical transistors with stability in water
journal, October 2016
- Giovannitti, Alexander; Nielsen, Christian B.; Sbircea, Dan-Tiberiu
- Nature Communications, Vol. 7, Issue 1
The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes
journal, April 2018
- Giovannitti, Alexander; Maria, Iuliana P.; Hanifi, David
- Chemistry of Materials, Vol. 30, Issue 9
Side Chain Redistribution as a Strategy to Boost Organic Electrochemical Transistor Performance and Stability
journal, August 2020
- Moser, Maximilian; Hidalgo, Tania Cecilia; Surgailis, Jokubas
- Advanced Materials, Vol. 32, Issue 37
Fullerene Adducts Bearing Cyano Moiety for Both High Dielectric Constant and Good Active Layer Morphology of Organic Photovoltaics
journal, June 2016
- Zhang, Sheng; Zhang, Zijian; Liu, Jun
- Advanced Functional Materials, Vol. 26, Issue 33
Balancing Charge Storage and Mobility in an Oligo(Ether) Functionalized Dioxythiophene Copolymer for Organic‐ and Aqueous‐ Based Electrochemical Devices and Transistors
journal, August 2018
- Savagian, Lisa R.; Österholm, Anna M.; Ponder, James F.
- Advanced Materials, Vol. 30, Issue 50
Functionalized Organic Thin Film Transistors for Biosensing
journal, January 2019
- Wang, Naixiang; Yang, Anneng; Fu, Ying
- Accounts of Chemical Research, Vol. 52, Issue 2
High transconductance organic electrochemical transistors
journal, July 2013
- Khodagholy, Dion; Rivnay, Jonathan; Sessolo, Michele
- Nature Communications, Vol. 4, Issue 1
Strategy for Enhancing the Dielectric Constant of Organic Semiconductors Without Sacrificing Charge Carrier Mobility and Solubility
journal, October 2014
- Torabi, Solmaz; Jahani, Fatemeh; Van Severen, Ineke
- Advanced Functional Materials, Vol. 25, Issue 1
Controlling the mode of operation of organic transistors through side-chain engineering
journal, October 2016
- Giovannitti, Alexander; Sbircea, Dan-Tiberiu; Inal, Sahika
- Proceedings of the National Academy of Sciences, Vol. 113, Issue 43
Recent Advances in Bulk Heterojunction Polymer Solar Cells
journal, August 2015
- Lu, Luyao; Zheng, Tianyue; Wu, Qinghe
- Chemical Reviews, Vol. 115, Issue 23
The effect of aromatic ring size in electron deficient semiconducting polymers for n-type organic thermoelectrics
journal, January 2020
- Alsufyani, Maryam; Hallani, Rawad K.; Wang, Suhao
- Journal of Materials Chemistry C, Vol. 8, Issue 43
Anthracenedicarboximides as Air-Stable N-Channel Semiconductors for Thin-Film Transistors with Remarkable Current On−Off Ratios
journal, October 2007
- Wang, Zhiming; Kim, Choongik; Facchetti, Antonio
- Journal of the American Chemical Society, Vol. 129, Issue 44, p. 13362-13363
Towards woven logic from organic electronic fibres
journal, April 2007
- Hamedi, Mahiar; Forchheimer, Robert; Inganäs, Olle
- Nature Materials, Vol. 6, Issue 5, p. 357-362
Comparison of the electrical characteristics of four 2,5-substituted poly(p-phenylene vinylene) derivatives with different side chains
journal, July 2006
- Breselge, M.; Van Severen, I.; Lutsen, L.
- Thin Solid Films, Vol. 511-512
Electrochemical strain microscopy probes morphology-induced variations in ion uptake and performance in organic electrochemical transistors
journal, June 2017
- Giridharagopal, R.; Flagg, L. Q.; Harrison, J. S.
- Nature Materials, Vol. 16, Issue 7
Understanding the Electronic Properties of Acceptor–Acceptor′–Acceptor Triads
journal, March 2019
- Zaugg, Kelly; Velasco, John; Robins, Kathleen A.
- ACS Omega, Vol. 4, Issue 3
Ion-Selective Organic Electrochemical Transistors
journal, May 2014
- Sessolo, Michele; Rivnay, Jonathan; Bandiello, Enrico
- Advanced Materials, Vol. 26, Issue 28
Donor–Acceptor‐Conjugated Polymer for High‐Performance Organic Field‐Effect Transistors: A Progress Report
journal, August 2019
- Kim, Minjun; Ryu, Seung Un; Park, Sang Ah
- Advanced Functional Materials, Vol. 30, Issue 20
Balancing Ionic and Electronic Conduction for High‐Performance Organic Electrochemical Transistors
journal, January 2020
- Savva, Achilleas; Hallani, Rawad; Cendra, Camila
- Advanced Functional Materials, Vol. 30, Issue 11
Fused electron deficient semiconducting polymers for air stable electron transport
journal, January 2018
- Onwubiko, Ada; Yue, Wan; Jellett, Cameron
- Nature Communications, Vol. 9, Issue 1
Polymer Crystallinity Controls Water Uptake in Glycol Side-Chain Polymer Organic Electrochemical Transistors
journal, February 2019
- Flagg, Lucas Q.; Bischak, Connor G.; Onorato, Jonathan W.
- Journal of the American Chemical Society, Vol. 141, Issue 10
High-Molecular-Weight Regular Alternating Diketopyrrolopyrrole-based Terpolymers for Efficient Organic Solar Cells
journal, June 2013
- Hendriks, Koen H.; Heintges, Gaël H. L.; Gevaerts, Veronique S.
- Angewandte Chemie, Vol. 125, Issue 32