Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics

David Kiefer; Alexander Giovannitti; Hengda Sun; Till Biskup; Anna Hofmann; Marten Koopmans; Camila Cendra; Stefan Weber; L. Jan Anton Koster; Eva Olsson; Jonathan Rivnay; Simone Fabiano; Iain McCulloch; Christian Müller

doi:10.1021/acsenergylett.7b01146

Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics

David Kiefer, Alexander Giovannitti, Hengda Sun, Till Biskup, Anna Hofmann, Marten Koopmans, Camila Cendra, Stefan Weber, L. Jan Anton Koster, Eva Olsson, Jonathan Rivnay, Simone Fabiano, Iain McCulloch, Christian Müller^*

^*Corresponding author for this work

Biomedical Engineering

Research output: Contribution to journal › Article › peer-review

182 Scopus citations

Abstract

N-doping of conjugated polymers either requires a high dopant fraction or yields a low electrical conductivity because of their poor compatibility with molecular dopants. We explore n-doping of the polar naphthalenediimide-bithiophene copolymer p(gNDI-gT2) that carries oligoethylene glycol-based side chains and show that the polymer displays superior miscibility with the benzimidazole-dimethylbenzenamine-based n-dopant N-DMBI. The good compatibility of p(gNDI-gT2) and N-DMBI results in a relatively high doping efficiency of 13% for n-dopants, which leads to a high electrical conductivity of more than 10^-1 S cm^-1 for a dopant concentration of only 10 mol % when measured in an inert atmosphere. We find that the doped polymer is able to maintain its electrical conductivity for about 20 min when exposed to air and recovers rapidly when returned to a nitrogen atmosphere. Overall, solution coprocessing of p(gNDI-gT2) and N-DMBI results in a larger thermoelectric power factor of up to 0.4 μW K^-2 m^-1 compared to other NDI-based polymers.

Original language	English (US)
Pages (from-to)	278-285
Number of pages	8
Journal	ACS Energy Letters
Volume	3
Issue number	2
DOIs	https://doi.org/10.1021/acsenergylett.7b01146
State	Published - Feb 9 2018

ASJC Scopus subject areas

Chemistry (miscellaneous)
Renewable Energy, Sustainability and the Environment
Fuel Technology
Energy Engineering and Power Technology
Materials Chemistry

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10.1021/acsenergylett.7b01146

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Kiefer, D., Giovannitti, A., Sun, H., Biskup, T., Hofmann, A., Koopmans, M., Cendra, C., Weber, S., Anton Koster, L. J., Olsson, E., Rivnay, J., Fabiano, S., McCulloch, I., & Müller, C. (2018). Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics. ACS Energy Letters, 3(2), 278-285. https://doi.org/10.1021/acsenergylett.7b01146

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title = "Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics",

abstract = "N-doping of conjugated polymers either requires a high dopant fraction or yields a low electrical conductivity because of their poor compatibility with molecular dopants. We explore n-doping of the polar naphthalenediimide-bithiophene copolymer p(gNDI-gT2) that carries oligoethylene glycol-based side chains and show that the polymer displays superior miscibility with the benzimidazole-dimethylbenzenamine-based n-dopant N-DMBI. The good compatibility of p(gNDI-gT2) and N-DMBI results in a relatively high doping efficiency of 13% for n-dopants, which leads to a high electrical conductivity of more than 10-1 S cm-1 for a dopant concentration of only 10 mol % when measured in an inert atmosphere. We find that the doped polymer is able to maintain its electrical conductivity for about 20 min when exposed to air and recovers rapidly when returned to a nitrogen atmosphere. Overall, solution coprocessing of p(gNDI-gT2) and N-DMBI results in a larger thermoelectric power factor of up to 0.4 μW K-2 m-1 compared to other NDI-based polymers.",

author = "David Kiefer and Alexander Giovannitti and Hengda Sun and Till Biskup and Anna Hofmann and Marten Koopmans and Camila Cendra and Stefan Weber and {Anton Koster}, {L. Jan} and Eva Olsson and Jonathan Rivnay and Simone Fabiano and Iain McCulloch and Christian M{\"u}ller",

note = "Funding Information: We gratefully acknowledge financial support from the Swedish Research Council through Grant No. 2016-06146, the Knut and Alice Wallenberg Foundation through a Wallenberg Academy Fellowship and the European Research Council (ERC) under Grant Agreement No. 637624. S.F. gratefully acknowledges support from VINNOVA (2015-04859) and the Swedish Research Council (2016-03979). Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource a national user facility operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. Funding Information: We gratefully acknowledge financial support from the Swedish Research Council through Grant No. 2016-06146, the Knut and Alice Wallenberg Foundation through a Wallenberg Academy Fellowship, and the European Research Council (ERC) under Grant Agreement No. 637624. S.F. gratefully acknowledges support from VINNOVA (2015-04859) and the Swedish Research Council (2016-03979). Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource, a national user facility operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acsenergylett.7b01146",

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Kiefer, D, Giovannitti, A, Sun, H, Biskup, T, Hofmann, A, Koopmans, M, Cendra, C, Weber, S, Anton Koster, LJ, Olsson, E, Rivnay, J, Fabiano, S, McCulloch, I & Müller, C 2018, 'Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics', ACS Energy Letters, vol. 3, no. 2, pp. 278-285. https://doi.org/10.1021/acsenergylett.7b01146

TY - JOUR

T1 - Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics

AU - Kiefer, David

AU - Giovannitti, Alexander

AU - Sun, Hengda

AU - Biskup, Till

AU - Hofmann, Anna

AU - Koopmans, Marten

AU - Cendra, Camila

AU - Weber, Stefan

AU - Anton Koster, L. Jan

AU - Olsson, Eva

AU - Rivnay, Jonathan

AU - Fabiano, Simone

AU - McCulloch, Iain

AU - Müller, Christian

N1 - Funding Information: We gratefully acknowledge financial support from the Swedish Research Council through Grant No. 2016-06146, the Knut and Alice Wallenberg Foundation through a Wallenberg Academy Fellowship and the European Research Council (ERC) under Grant Agreement No. 637624. S.F. gratefully acknowledges support from VINNOVA (2015-04859) and the Swedish Research Council (2016-03979). Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource a national user facility operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. Funding Information: We gratefully acknowledge financial support from the Swedish Research Council through Grant No. 2016-06146, the Knut and Alice Wallenberg Foundation through a Wallenberg Academy Fellowship, and the European Research Council (ERC) under Grant Agreement No. 637624. S.F. gratefully acknowledges support from VINNOVA (2015-04859) and the Swedish Research Council (2016-03979). Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource, a national user facility operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/2/9

Y1 - 2018/2/9

N2 - N-doping of conjugated polymers either requires a high dopant fraction or yields a low electrical conductivity because of their poor compatibility with molecular dopants. We explore n-doping of the polar naphthalenediimide-bithiophene copolymer p(gNDI-gT2) that carries oligoethylene glycol-based side chains and show that the polymer displays superior miscibility with the benzimidazole-dimethylbenzenamine-based n-dopant N-DMBI. The good compatibility of p(gNDI-gT2) and N-DMBI results in a relatively high doping efficiency of 13% for n-dopants, which leads to a high electrical conductivity of more than 10-1 S cm-1 for a dopant concentration of only 10 mol % when measured in an inert atmosphere. We find that the doped polymer is able to maintain its electrical conductivity for about 20 min when exposed to air and recovers rapidly when returned to a nitrogen atmosphere. Overall, solution coprocessing of p(gNDI-gT2) and N-DMBI results in a larger thermoelectric power factor of up to 0.4 μW K-2 m-1 compared to other NDI-based polymers.

AB - N-doping of conjugated polymers either requires a high dopant fraction or yields a low electrical conductivity because of their poor compatibility with molecular dopants. We explore n-doping of the polar naphthalenediimide-bithiophene copolymer p(gNDI-gT2) that carries oligoethylene glycol-based side chains and show that the polymer displays superior miscibility with the benzimidazole-dimethylbenzenamine-based n-dopant N-DMBI. The good compatibility of p(gNDI-gT2) and N-DMBI results in a relatively high doping efficiency of 13% for n-dopants, which leads to a high electrical conductivity of more than 10-1 S cm-1 for a dopant concentration of only 10 mol % when measured in an inert atmosphere. We find that the doped polymer is able to maintain its electrical conductivity for about 20 min when exposed to air and recovers rapidly when returned to a nitrogen atmosphere. Overall, solution coprocessing of p(gNDI-gT2) and N-DMBI results in a larger thermoelectric power factor of up to 0.4 μW K-2 m-1 compared to other NDI-based polymers.

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U2 - 10.1021/acsenergylett.7b01146

DO - 10.1021/acsenergylett.7b01146

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AN - SCOPUS:85041806115

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JO - ACS Energy Letters

JF - ACS Energy Letters

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ER -

Enhanced n-Doping Efficiency of a Naphthalenediimide-Based Copolymer through Polar Side Chains for Organic Thermoelectrics

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