Authors
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Liu, W. ; Tkachov, R. ; Komber, H. ; Senkovskyy, V. ; Schubert, M. ; Wei, Z. ; Facchetti, A. ; Neher, D. ; Kiriy, A.
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Title
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Chain-growth polycondensation of perylene diimide-based copolymers: a new route to regioregular perylene diimide-based acceptors for all-polymer solar cells and n-type transistors
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Date
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21.05.2014
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Number
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43642
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Abstract
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Herein, we report the chain-growth tin-free room temperature polymerization method to synthesize n-type perylene diimide-dithiophene-based conjugated polymers (PPDIT2s) suitable for solar cell and transistor applications. The palladium/electron-rich tri-tert-butylphosphine catalyst is effective to enable the chain-growth polymerization of anion-radical monomer Br-TPDIT-Br/Zn to PPDIT2 with a molecular weight up to Mw 50 kg mol-1 and moderate polydispersity. This is the second example of the polymerization of unusual anion-radical aromatic complexes formed in a reaction of active Zn and electron-deficient diimide-based aryl halides. As such, the discovered polymerization method is not a specific reactivity feature of the naphthalene-diimide derivatives but is rather a general polymerization tool. This is an important finding, given the significantly higher maximum external quantum efficiency that can be reached with PDI-based copolymers (3245%) in all-polymer solar cells compared to NDI-based materials (1530%). Our studies revealed that PPDIT2 synthesized by the new method and the previously published polymer prepared by step-growth Stille polycondensation show similar electron mobility and all-polymer solar cell performance. At the same time, the polymerization reported herein has several technological advantages as it proceeds relatively fast at room temperature and does not involve toxic tin-based compounds. Because several chain-growth polymerization reactions are well-suited for the preparation of well-defined multi-functional polymer architectures, the next target is to explore the utility of the discovered polymerization in the synthesis of end-functionalized polymers and block copolymers. Such materials would be helpful to improve the nanoscale morphology of polymer blends in all-polymer solar cells.
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Publisher
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Polymer Chemistry
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Wikidata
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Citation
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Polymer Chemistry 5 (2014) 3404-3411
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DOI
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https://doi.org/10.1039/C3PY01707A
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Tags
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