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Title: The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes

Abstract

Here, we report a design strategy that allows the preparation of solution processable n-type materials from low boiling point solvents for organic electrochemical transistors (OECTs). The polymer backbone is based on NDI-T2 copolymers where a branched alkyl side chain is gradually exchanged for a linear ethylene glycol-based side chain. A series of random copolymers was prepared with glycol side chain percentages of 0, 10, 25, 50, 75, 90, and 100 with respect to the alkyl side chains. These were characterized to study the influence of the polar side chains on interaction with aqueous electrolytes, their electrochemical redox reactions, and performance in OECTs when operated in aqueous electrolytes. We observed that glycol side chain percentages of >50% are required to achieve volumetric charging, while lower glycol chain percentages show a mixed operation with high required voltages to allow for bulk charging of the organic semiconductor. A strong dependence of the electron mobility on the fraction of glycol chains was found for copolymers based on NDI-T2, with a significant drop as alkyl side chains are replaced by glycol side chains.

Authors:
ORCiD logo [1];  [2];  [3];  [4];  [5];  [6];  [6];  [7];  [8];  [8]; ORCiD logo [8];  [9];  [7]; ORCiD logo [10]; ORCiD logo [11];  [8];  [12]; ORCiD logo [13]
  1. Imperial College, London (United Kingdom). Dept. of Chemistry, Dept. of Physics and Centre for Plastic Electronics
  2. Imperial College, London (United Kingdom). Dept. of Chemistry
  3. Stanford Univ., CA (United States). Dept. of Chemistry
  4. Mines ParisTech, CMP-EMSE, Paris (France). Dept. of Bioelectronics
  5. King Abdullah Univ. of Science and Technology (KAUST), Thuwal (Saudi Arabia). Physical Sciences and Engineering Division and KAUST Solar Center (KSC)
  6. Northwestern Univ., Evanston, IL (United States). Dept. of Biomedical Engineering
  7. King Abdullah Univ. of Science and Technology (KAUST), Thuwal (Saudi Arabia). Biological and Environmental Science and Engineering
  8. Imperial College, London (United Kingdom). Dept. of Physics and Centre for Plastic Electronics
  9. Univ. of Colorado, Boulder, CO (United States). Renewable and Sustainable Energy Inst.; National Renewable Energy Lab. (NREL), Golden, CO (United States). Chemistry and Nanoscience Center
  10. Univ. of Colorado, Boulder, CO (United States). Renewable and Sustainable Energy Inst. and Dept. of Chemistry and Biochemistry; National Renewable Energy Lab. (NREL), Golden, CO (United States). Chemistry and Nanoscience Center
  11. Univ. of Cambridge (United Kingdom). Electrical Engineering Division
  12. Northwestern Univ., Evanston, IL (United States). Dept. of Biomedical Engineering and Simpson Querry Inst. for BioNanotechnology
  13. Imperial College, London (United Kingdom). Dept. of Chemistry; King Abdullah Univ. of Science and Technology (KAUST), Thuwal (Saudi Arabia). Physical Sciences and Engineering Division and KAUST Solar Center (KSC)
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division; BASF SE, Ludwigshafen (Germany); Engineering and Physical Sciences Research Council (EPSRC); European Research Council (ERC); European Union (EU); National Science Foundation (NSF)
OSTI Identifier:
1440398
Report Number(s):
NREL/JA-5900-71212
Journal ID: ISSN 0897-4756
Grant/Contract Number:  
AC36-08GO28308; EP/P02484X/1; EP/G037515/1; EP/M005143/1; EP/N509486/1; EC FP7 Project SC2 (610115); EC H2020 Project SOLEDLIGHT (643791); 742708
Resource Type:
Accepted Manuscript
Journal Name:
Chemistry of Materials
Additional Journal Information:
Journal Volume: 30; Journal Issue: 9; Journal ID: ISSN 0897-4756
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE; n-type materials; organic electrochemical transistors

Citation Formats

Giovannitti, Alexander, Maria, Iuliana P., Hanifi, David, Donahue, Mary J., Bryant, Daniel, Barth, Katrina J., Makdah, Beatrice E., Savva, Achilleas, Moia, Davide, Zetek, Matyas, Barnes, Piers R. F., Reid, Obadiah G., Inal, Sahika, Rumbles, Garry, Malliaras, George G., Nelson, Jenny, Rivnay, Jonathan, and McCulloch, Iain. The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes. United States: N. p., 2018. Web. doi:10.1021/acs.chemmater.8b00321.
Giovannitti, Alexander, Maria, Iuliana P., Hanifi, David, Donahue, Mary J., Bryant, Daniel, Barth, Katrina J., Makdah, Beatrice E., Savva, Achilleas, Moia, Davide, Zetek, Matyas, Barnes, Piers R. F., Reid, Obadiah G., Inal, Sahika, Rumbles, Garry, Malliaras, George G., Nelson, Jenny, Rivnay, Jonathan, & McCulloch, Iain. The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes. United States. doi:https://doi.org/10.1021/acs.chemmater.8b00321
Giovannitti, Alexander, Maria, Iuliana P., Hanifi, David, Donahue, Mary J., Bryant, Daniel, Barth, Katrina J., Makdah, Beatrice E., Savva, Achilleas, Moia, Davide, Zetek, Matyas, Barnes, Piers R. F., Reid, Obadiah G., Inal, Sahika, Rumbles, Garry, Malliaras, George G., Nelson, Jenny, Rivnay, Jonathan, and McCulloch, Iain. Tue . "The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes". United States. doi:https://doi.org/10.1021/acs.chemmater.8b00321. https://www.osti.gov/servlets/purl/1440398.
@article{osti_1440398,
title = {The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes},
author = {Giovannitti, Alexander and Maria, Iuliana P. and Hanifi, David and Donahue, Mary J. and Bryant, Daniel and Barth, Katrina J. and Makdah, Beatrice E. and Savva, Achilleas and Moia, Davide and Zetek, Matyas and Barnes, Piers R. F. and Reid, Obadiah G. and Inal, Sahika and Rumbles, Garry and Malliaras, George G. and Nelson, Jenny and Rivnay, Jonathan and McCulloch, Iain},
abstractNote = {Here, we report a design strategy that allows the preparation of solution processable n-type materials from low boiling point solvents for organic electrochemical transistors (OECTs). The polymer backbone is based on NDI-T2 copolymers where a branched alkyl side chain is gradually exchanged for a linear ethylene glycol-based side chain. A series of random copolymers was prepared with glycol side chain percentages of 0, 10, 25, 50, 75, 90, and 100 with respect to the alkyl side chains. These were characterized to study the influence of the polar side chains on interaction with aqueous electrolytes, their electrochemical redox reactions, and performance in OECTs when operated in aqueous electrolytes. We observed that glycol side chain percentages of >50% are required to achieve volumetric charging, while lower glycol chain percentages show a mixed operation with high required voltages to allow for bulk charging of the organic semiconductor. A strong dependence of the electron mobility on the fraction of glycol chains was found for copolymers based on NDI-T2, with a significant drop as alkyl side chains are replaced by glycol side chains.},
doi = {10.1021/acs.chemmater.8b00321},
journal = {Chemistry of Materials},
number = 9,
volume = 30,
place = {United States},
year = {2018},
month = {4}
}

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