Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties

Astrid Caroline Knall; Sebastian Franz Hoefler; Manuel Hollauf; Ferula Thaler; Sven Noesberger; Ilie Hanzu; Heike Ehmann; Mathias Hobisch; Stefan Spirk; Shuguang Wen; Renqiang Yang; Thomas Rath; Gregor Trimmel

doi:10.1007/s10853-019-03551-3

Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties

Astrid Caroline Knall, Sebastian Franz Hoefler, Manuel Hollauf, Ferula Thaler, Sven Noesberger, Ilie Hanzu, Heike Ehmann, Mathias Hobisch, Stefan Spirk, Shuguang Wen, Renqiang Yang, Thomas Rath^*, Gregor Trimmel

^*Corresponding author for this work

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

Abstract

Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-1,2,4,5-tetrazine (2OD-TTz). Palladium-catalyzed copolymerization of 2OD-TTz with a bithiophene monomer yielded an alternating tetrazine–quaterthiophene copolymer (PTz4T-2OD). The polymer PTz4T-2OD showed an optical band gap of 1.8 eV, a deep HOMO energy level of − 5.58 eV and good solubility. In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained.

Original language	English
Pages (from-to)	10065–10076
Number of pages	12
Journal	Journal of Materials Science
Volume	54
Issue number	13
DOIs	https://doi.org/10.1007/s10853-019-03551-3
Publication status	Published - 2019

ASJC Scopus subject areas

General Materials Science
Mechanics of Materials
Mechanical Engineering

Fields of Expertise

Advanced Materials Science

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1007/s10853-019-03551-3

Cite this

Knall, A. C., Hoefler, S. F., Hollauf, M., Thaler, F., Noesberger, S., Hanzu, I., Ehmann, H., Hobisch, M., Spirk, S., Wen, S., Yang, R., Rath, T., & Trimmel, G. (2019). Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties. Journal of Materials Science, 54(13), 10065–10076. https://doi.org/10.1007/s10853-019-03551-3

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abstract = "Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-1,2,4,5-tetrazine (2OD-TTz). Palladium-catalyzed copolymerization of 2OD-TTz with a bithiophene monomer yielded an alternating tetrazine–quaterthiophene copolymer (PTz4T-2OD). The polymer PTz4T-2OD showed an optical band gap of 1.8 eV, a deep HOMO energy level of − 5.58 eV and good solubility. In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained.",

author = "Knall, {Astrid Caroline} and Hoefler, {Sebastian Franz} and Manuel Hollauf and Ferula Thaler and Sven Noesberger and Ilie Hanzu and Heike Ehmann and Mathias Hobisch and Stefan Spirk and Shuguang Wen and Renqiang Yang and Thomas Rath and Gregor Trimmel",

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doi = "10.1007/s10853-019-03551-3",

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T1 - Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties

AU - Knall, Astrid Caroline

AU - Hoefler, Sebastian Franz

AU - Hollauf, Manuel

AU - Thaler, Ferula

AU - Noesberger, Sven

AU - Hanzu, Ilie

AU - Ehmann, Heike

AU - Hobisch, Mathias

AU - Spirk, Stefan

AU - Wen, Shuguang

AU - Yang, Renqiang

AU - Rath, Thomas

AU - Trimmel, Gregor

PY - 2019

Y1 - 2019

N2 - Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-1,2,4,5-tetrazine (2OD-TTz). Palladium-catalyzed copolymerization of 2OD-TTz with a bithiophene monomer yielded an alternating tetrazine–quaterthiophene copolymer (PTz4T-2OD). The polymer PTz4T-2OD showed an optical band gap of 1.8 eV, a deep HOMO energy level of − 5.58 eV and good solubility. In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained.

AB - Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-1,2,4,5-tetrazine (2OD-TTz). Palladium-catalyzed copolymerization of 2OD-TTz with a bithiophene monomer yielded an alternating tetrazine–quaterthiophene copolymer (PTz4T-2OD). The polymer PTz4T-2OD showed an optical band gap of 1.8 eV, a deep HOMO energy level of − 5.58 eV and good solubility. In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained.

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Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties

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Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties

Abstract

ASJC Scopus subject areas

Fields of Expertise

UN SDGs

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