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

Alexander Giovannitti, Iuliana P. Maria, David Hanifi, Mary J. Donahue, Daniel Bryant, Katrina J. Barth, Beatrice E. Makdah, Achilleas Savva, Davide Moia, Matyáš Zetek, Piers R.F. Barnes, Obadiah G. Reid, Sahika Inal, Gary Rumbles, George G. Malliaras, Jenny Nelson, Jonathan Rivnay, Iain McCulloch

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2945-2953
Number of pages9
JournalChemistry of Materials
Volume30
Issue number9
DOIs
Publication statusPublished - May 8 2018

Fingerprint

Glycols
Conjugated polymers
Electrolytes
Copolymers
Transistors
Semiconducting organic compounds
Ethylene Glycol
Electron mobility
Redox reactions
Boiling point
Ethylene glycol
Polymers
Electric potential

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

Cite this

Giovannitti, A., Maria, I. P., Hanifi, D., Donahue, M. J., Bryant, D., Barth, K. J., ... McCulloch, I. (2018). The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes. Chemistry of Materials, 30(9), 2945-2953. https://doi.org/10.1021/acs.chemmater.8b00321

The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes. / Giovannitti, Alexander; Maria, Iuliana P.; Hanifi, David; Donahue, Mary J.; Bryant, Daniel; Barth, Katrina J.; Makdah, Beatrice E.; Savva, Achilleas; Moia, Davide; Zetek, Matyáš; Barnes, Piers R.F.; Reid, Obadiah G.; Inal, Sahika; Rumbles, Gary; Malliaras, George G.; Nelson, Jenny; Rivnay, Jonathan; McCulloch, Iain.

In: Chemistry of Materials, Vol. 30, No. 9, 08.05.2018, p. 2945-2953.

Research output: Contribution to journalArticle

Giovannitti, A, Maria, IP, Hanifi, D, Donahue, MJ, Bryant, D, Barth, KJ, Makdah, BE, Savva, A, Moia, D, Zetek, M, Barnes, PRF, Reid, OG, Inal, S, Rumbles, G, Malliaras, GG, Nelson, J, Rivnay, J & McCulloch, I 2018, 'The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes', Chemistry of Materials, vol. 30, no. 9, pp. 2945-2953. 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, Matyáš ; Barnes, Piers R.F. ; Reid, Obadiah G. ; Inal, Sahika ; Rumbles, Gary ; 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. In: Chemistry of Materials. 2018 ; Vol. 30, No. 9. pp. 2945-2953.
@article{e8eb0df1108a4cb29b1adb733a36e079,
title = "The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes",
abstract = "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.",
author = "Alexander Giovannitti and Maria, {Iuliana P.} and David Hanifi and Donahue, {Mary J.} and Daniel Bryant and Barth, {Katrina J.} and Makdah, {Beatrice E.} and Achilleas Savva and Davide Moia and Maty{\'a}š Zetek and Barnes, {Piers R.F.} and Reid, {Obadiah G.} and Sahika Inal and Gary Rumbles and Malliaras, {George G.} and Jenny Nelson and Jonathan Rivnay and Iain McCulloch",
year = "2018",
month = "5",
day = "8",
doi = "10.1021/acs.chemmater.8b00321",
language = "English",
volume = "30",
pages = "2945--2953",
journal = "Chemistry of Materials",
issn = "0897-4756",
publisher = "American Chemical Society",
number = "9",

}

TY - JOUR

T1 - The Role of the Side Chain on the Performance of N-type Conjugated Polymers in Aqueous Electrolytes

AU - Giovannitti, Alexander

AU - Maria, Iuliana P.

AU - Hanifi, David

AU - Donahue, Mary J.

AU - Bryant, Daniel

AU - Barth, Katrina J.

AU - Makdah, Beatrice E.

AU - Savva, Achilleas

AU - Moia, Davide

AU - Zetek, Matyáš

AU - Barnes, Piers R.F.

AU - Reid, Obadiah G.

AU - Inal, Sahika

AU - Rumbles, Gary

AU - Malliaras, George G.

AU - Nelson, Jenny

AU - Rivnay, Jonathan

AU - McCulloch, Iain

PY - 2018/5/8

Y1 - 2018/5/8

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85046623667&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85046623667&partnerID=8YFLogxK

U2 - 10.1021/acs.chemmater.8b00321

DO - 10.1021/acs.chemmater.8b00321

M3 - Article

VL - 30

SP - 2945

EP - 2953

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 9

ER -