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

Research output: Contribution to journalArticleResearchpeer-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 languageEnglish
Pages (from-to)10065–10076
Number of pages12
JournalJournal of Materials Science
Volume54
Issue number13
DOIs
Publication statusPublished - 2019

Fingerprint

Thiophenes
Nitriles
Conjugated polymers
Optical band gaps
Palladium
Thiophene
Copolymerization
Electron energy levels
Conversion efficiency
Solar cells
Polymers
Copolymers
Solubility
Monomers
Electrons

ASJC Scopus subject areas

  • Materials Science(all)
  • Mechanics of Materials
  • Mechanical Engineering

Fields of Expertise

  • Advanced Materials Science

Cite this

Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties. / Knall, Astrid Caroline; Hoefler, Sebastian Franz; Hollauf, Manuel; Thaler, Ferula; Noesberger, Sven; Hanzu, Ilie; Ehmann, Heike; Hobisch, Mathias; Spirk, Stefan; Wen, Shuguang; Yang, Renqiang; Rath, Thomas; Trimmel, Gregor.

In: Journal of Materials Science, Vol. 54, No. 13, 2019, p. 10065–10076.

Research output: Contribution to journalArticleResearchpeer-review

Knall, Astrid Caroline ; Hoefler, Sebastian Franz ; Hollauf, Manuel ; Thaler, Ferula ; Noesberger, Sven ; Hanzu, Ilie ; Ehmann, Heike ; Hobisch, Mathias ; Spirk, Stefan ; Wen, Shuguang ; Yang, Renqiang ; Rath, Thomas ; Trimmel, Gregor. / Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties. In: Journal of Materials Science. 2019 ; Vol. 54, No. 13. pp. 10065–10076.
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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

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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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