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; Garry Rumbles; George G. Malliaras; Jenny Nelson; Jonathan Rivnay; Iain McCulloch

doi:10.1021/acs.chemmater.8b00321

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, Garry Rumbles, George G. Malliaras, Jenny Nelson, Jonathan Rivnay, Iain McCulloch

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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 language	English (US)
Pages (from-to)	2945-2953
Number of pages	9
Journal	Chemistry of Materials
Volume	30
Issue number	9
DOIs	https://doi.org/10.1021/acs.chemmater.8b00321
State	Published - Apr 24 2018

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We thank Iain Hamilton for assistance in measuring contact angle data and Nathan Cheetham for recording solid state absorption spectra. We acknowledge funding from KAUST and BASF, as well as EPSRC Projects EP/P02484X/1, EP/G037515/1, EP/M005143/1, EP/N509486/1; EC FP7 Project SC2 (610115); and EC H2020 Project SOLEDLIGHT (643791) In addition, this project has received funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program (grant agreement No 742708). O.G.R. and G.R. acknowledge support for the microwave conductivity and photoluminescence measurements from the Solar Photochemistry Program, Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences, U.S. Department of Energy under Contract DE-AC36-08-GO28308 with the National Renewable Energy Laboratory. D.H. gratefully acknowledges support from NSF-GFRP.

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10.1021/acs.chemmater.8b00321

https://repository.kaust.edu.sa/bitstream/10754/627699/1/acs.chemmater.8b00321.pdf

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Giovannitti, A., Maria, I. P., Hanifi, D., Donahue, M. J., Bryant, D., Barth, K. J., Makdah, B. E., Savva, A., Moia, D., Zetek, M., Barnes, P. R. F., Reid, O. G., Inal, S., Rumbles, G., Malliaras, G. G., 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, 30(9), 2945-2953. https://doi.org/10.1021/acs.chemmater.8b00321

@article{395b862b9157461d95f1203923f2e43e,

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}{\v s} Zetek and Barnes, {Piers R.F.} and Reid, {Obadiah G.} and Sahika Inal and Garry Rumbles and Malliaras, {George G.} and Jenny Nelson and Jonathan Rivnay and Iain McCulloch",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Iain Hamilton for assistance in measuring contact angle data and Nathan Cheetham for recording solid state absorption spectra. We acknowledge funding from KAUST and BASF, as well as EPSRC Projects EP/P02484X/1, EP/G037515/1, EP/M005143/1, EP/N509486/1; EC FP7 Project SC2 (610115); and EC H2020 Project SOLEDLIGHT (643791) In addition, this project has received funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program (grant agreement No 742708). O.G.R. and G.R. acknowledge support for the microwave conductivity and photoluminescence measurements from the Solar Photochemistry Program, Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences, U.S. Department of Energy under Contract DE-AC36-08-GO28308 with the National Renewable Energy Laboratory. D.H. gratefully acknowledges support from NSF-GFRP.",

year = "2018",

month = apr,

day = "24",

doi = "10.1021/acs.chemmater.8b00321",

language = "English (US)",

volume = "30",

pages = "2945--2953",

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publisher = "American Chemical Society",

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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

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, Garry

AU - Malliaras, George G.

AU - Nelson, Jenny

AU - Rivnay, Jonathan

AU - McCulloch, Iain

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Iain Hamilton for assistance in measuring contact angle data and Nathan Cheetham for recording solid state absorption spectra. We acknowledge funding from KAUST and BASF, as well as EPSRC Projects EP/P02484X/1, EP/G037515/1, EP/M005143/1, EP/N509486/1; EC FP7 Project SC2 (610115); and EC H2020 Project SOLEDLIGHT (643791) In addition, this project has received funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program (grant agreement No 742708). O.G.R. and G.R. acknowledge support for the microwave conductivity and photoluminescence measurements from the Solar Photochemistry Program, Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences, U.S. Department of Energy under Contract DE-AC36-08-GO28308 with the National Renewable Energy Laboratory. D.H. gratefully acknowledges support from NSF-GFRP.

PY - 2018/4/24

Y1 - 2018/4/24

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.

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UR - https://pubs.acs.org/doi/10.1021/acs.chemmater.8b00321

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

U2 - 10.1021/acs.chemmater.8b00321

DO - 10.1021/acs.chemmater.8b00321

M3 - Article

C2 - 29780208

SN - 0897-4756

VL - 30

SP - 2945

EP - 2953

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 9

ER -

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

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