Organogels from Diketopyrrolopyrrole Copolymer Ionene/Polythiophene Blends Exhibit Ground-State Single Electron Transfer in the Solid State
- Dominik StegererDominik StegererInstitut für Chemie, Technische Universität Chemnitz, 09111 Chemnitz, GermanyDepartment of Chemistry and Chemical Engineering, Chalmers University of Technology, 412 96 Göteborg, SwedenMore by Dominik Stegerer
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- Martin PrachtMartin PrachtInstitut für Chemie, Technische Universität Chemnitz, 09111 Chemnitz, GermanyMore by Martin Pracht
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- Florian GüntherFlorian GüntherInstituto de Física de Saõ Carlos, Universidade de Saõ Paulo, Saõ Paulo 05508-900, BrazilMore by Florian Günther
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- Hengda SunHengda SunLaboratory of Organic Electronics (LOE), Department of Science and Technology (ITN), Linköping University, 601 74 Norrköping, SwedenMore by Hengda Sun
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- Kevin PreisKevin PreisInstitut für Physik, Technische Universität Chemnitz, 09126 Chemnitz, GermanyMore by Kevin Preis
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- Mario ZersonMario ZersonInstitut für Chemie, Technische Universität Chemnitz, 09111 Chemnitz, GermanyInstitut für Physik, Technische Universität Chemnitz, 09126 Chemnitz, GermanyMore by Mario Zerson
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- Wafa MaftuhinWafa MaftuhinFreiburg Center for Interactive Materials and Bioinspired Technologies (FIT), Albert-Ludwigs-Universität Freiburg, 79110 Freiburg, GermanyMore by Wafa Maftuhin
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- Wen Liang TanWen Liang TanDepartment of Materials Science and Engineering, Monash University, Clayton, Victoria 3800, AustraliaMore by Wen Liang Tan
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- Renee KroonRenee KroonDepartment of Chemistry and Chemical Engineering, Chalmers University of Technology, 412 96 Göteborg, SwedenLaboratory of Organic Electronics (LOE), Department of Science and Technology (ITN), Linköping University, 601 74 Norrköping, SwedenMore by Renee Kroon
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- Christopher R. McNeillChristopher R. McNeillDepartment of Materials Science and Engineering, Monash University, Clayton, Victoria 3800, AustraliaMore by Christopher R. McNeill
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- Simone FabianoSimone FabianoLaboratory of Organic Electronics (LOE), Department of Science and Technology (ITN), Linköping University, 601 74 Norrköping, SwedenMore by Simone Fabiano
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- Michael WalterMichael WalterFreiburg Center for Interactive Materials and Bioinspired Technologies (FIT), Albert-Ludwigs-Universität Freiburg, 79110 Freiburg, GermanyMore by Michael Walter
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- Till BiskupTill BiskupPhysikalische Chemie und Didaktik der Chemie, Universität des Saarlandes, 66123 Saarbrücken, GermanyMore by Till Biskup
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- Sibylle GemmingSibylle GemmingInstitut für Physik, Technische Universität Chemnitz, 09126 Chemnitz, GermanyCenter for Materials, Architectures and Integration of Nanomembranes (MAIN), Technische Universität Chemnitz, Chemnitz 09126, GermanyMore by Sibylle Gemming
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- Robert MagerleRobert MagerleInstitut für Chemie, Technische Universität Chemnitz, 09111 Chemnitz, GermanyInstitut für Physik, Technische Universität Chemnitz, 09126 Chemnitz, GermanyMore by Robert Magerle
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- Christian MüllerChristian MüllerDepartment of Chemistry and Chemical Engineering, Chalmers University of Technology, 412 96 Göteborg, SwedenMore by Christian Müller
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- Michael Sommer*Michael Sommer*Email: [email protected]Institut für Chemie, Technische Universität Chemnitz, 09111 Chemnitz, GermanyCenter for Materials, Architectures and Integration of Nanomembranes (MAIN), Technische Universität Chemnitz, Chemnitz 09126, GermanyMore by Michael Sommer
Abstract
Acceptor copolymers with low lowest unoccupied molecular orbital (LUMO) energy levels are key materials for organic electronics. In the present work, quaternization of pyridine-flanked diketopyrrolopyrrole (PyDPPPy) is used to lower the LUMO energy level of the resulting monomer (MePyDPPPy) by as much as 0.7 eV. The drastically changed electronic properties of MePyDPPPy hinder a second methylation step even in an excess of trimethyloxonium tetrafluoroborate and thereby give access to the asymmetric functionalization of N-heterocycle-flanked DPP building blocks. The corresponding n-type polymeric ionene PMePyDPPPyT2 with bithiophene as comonomer forms thixotropic organogels with the p-type polythiophene P(g42T-TT), indicative of specific cross-interactions between this couple of copolymers. Gelation of polymer blend solutions, which is absent for other couples of p-type/ n-type polymers, is of general interest for (co)processing and orientation of different electronic polymers simultaneously into films or filaments. Detailed optical and electronic characterization reveals that films processed from organogels exhibit ground-state electron transfer (GSET) enabled by suitably positioned highest occupied molecular orbital (HOMO) and LUMO energy levels of P(g42T-TT) (−4.07 eV) and PMePyDPPPyT2 (−4.20 eV), respectively. Furthermore, molecular interactions related to gelation and GSET do not appear to significantly influence the morphology of the polymer blend films.
Cited By
This article is cited by 1 publications.
- Bo Zhang, Congwu Ge, Cong Xie, Kaiwen Lin, Wei Yang, Bingyong Liu, Xike Gao, Yinhua Zhou, Qing Zhang. Synthesis, characterization, and semiconducting properties of π-conjugated polymers containing hydrogen-bonded bis-pyridine-thieno[3,2-
b
]thiophene moieties. Journal of Materials Chemistry C 2022, 10
(46)
, 17530-17538. https://doi.org/10.1039/D2TC03958C