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Suppression of Homocoupling Side Reactions in Direct Arylation Polycondensation for Producing High Performance OPV Materials

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† Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
‡ Research Center for Functional Materials, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047, Japan
*E-mail [email protected] (J.K.).
*E-mail [email protected] (T.K.).
Cite this: Macromolecules 2016, 49, 24, 9388–9395
Publication Date (Web):December 15, 2016
https://doi.org/10.1021/acs.macromol.6b02380
Copyright © 2016 American Chemical Society
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Abstract

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Suppression of side reactions in C–H direct arylation polycondensation is important for developing this method as a reliable synthetic tool for conjugated polymer materials. To find appropriate reaction conditions for avoiding homocoupling side reactions, two types of reaction conditions were investigated: the direct arylation of electron-rich C–H monomers in N,N-dimethylacetamide (DMAc system) and the direct arylation of electron-poor C–H monomers in toluene (toluene system). The investigation reveals that homocoupling side reactions are suppressed under the toluene system. Because the combination of electron-poor C–H monomer (acceptor) and electron-rich C–Br monomer (donor) is applicable to the toluene system, a donor–acceptor polymer without a defect structure can be synthesized under the toluene system. The obtained polymer shows almost same power conversion efficiency (PCE) in bulk-heterojunction OPVs as the same polymer prepared by a conventional method and purified by Soxhlet extraction. These results show that the established direct arylation polycondensation affords a high-quality material in terms of both structural integrity and purity. OPV cells with an optimized device structure result in a maximum PCE of 6.8%.

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  • Characterization data for polymers and OPV device characteristics (PDF)

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This article is cited by 29 publications.

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  17. Junpei Kuwabara, Takaki Kanbara. Facile Synthesis of π-Conjugated Polymers via Direct Arylation Polycondensation. Bulletin of the Chemical Society of Japan 2019, 92 (1) , 152-161. https://doi.org/10.1246/bcsj.20180249
  18. Junpei Kuwabara. Direct arylation polycondensation for synthesis of optoelectronic materials. Polymer Journal 2018, 50 (12) , 1099-1106. https://doi.org/10.1038/s41428-018-0101-3
  19. Hassan Bohra, Hui Chen, Yanfen Peng, Amsalu Efrem, Feng He, Mingfeng Wang. Direct arylation polymerization toward efficient synthesis of benzo[1,2-c:4,5-c'] dithiophene-4,8-dione based donor-acceptor alternating copolymers for organic optoelectronic applications. Journal of Polymer Science Part A: Polymer Chemistry 2018, 56 (22) , 2554-2564. https://doi.org/10.1002/pola.29235
  20. Nemal S. Gobalasingham, Barry C. Thompson. Direct arylation polymerization: A guide to optimal conditions for effective conjugated polymers. Progress in Polymer Science 2018, 83 , 135-201. https://doi.org/10.1016/j.progpolymsci.2018.06.002
  21. Masayuki Wakioka, Fumiyuki Ozawa. Highly Efficient Catalysts for Direct Arylation Polymerization (DArP). Asian Journal of Organic Chemistry 2018, 7 (7) , 1206-1216. https://doi.org/10.1002/ajoc.201800227
  22. Kazuhiro Nakabayashi. Direct arylation polycondensation as conjugated polymer synthesis methodology. Polymer Journal 2018, 50 (7) , 475-483. https://doi.org/10.1038/s41428-018-0039-5
  23. Arthur Hendsbee, Yuning Li. Performance Comparisons of Polymer Semiconductors Synthesized by Direct (Hetero)Arylation Polymerization (DHAP) and Conventional Methods for Organic Thin Film Transistors and Organic Photovoltaics. Molecules 2018, 23 (6) , 1255. https://doi.org/10.3390/molecules23061255
  24. Robert M. Pankow, John D. Munteanu, Barry C. Thompson. Influence of the aryl spacer in 2,5-dialkoxyphenylene and diaryl substituted thieno[3,4- c ]pyrrole-4,6-dione copolymers. Journal of Materials Chemistry C 2018, 6 (22) , 5992-5998. https://doi.org/10.1039/C8TC00823J
  25. Robert M. Pankow, Nemal S. Gobalasingham, John D. Munteanu, Barry C. Thompson. Preparation of semi-alternating conjugated polymers using direct arylation polymerization (DArP) and improvement of photovoltaic device performance through structural variation. Journal of Polymer Science Part A: Polymer Chemistry 2017, 55 (20) , 3370-3380. https://doi.org/10.1002/pola.28712
  26. Shuhei Nishigaki, Miho Fukui, Haruki Sugiyama, Hidehiro Uekusa, Susumu Kawauchi, Yu Shibata, Ken Tanaka. Synthesis, Structures, and Photophysical Properties of Alternating Donor–Acceptor Cycloparaphenylenes. Chemistry – A European Journal 2017, 23 (30) , 7227-7231. https://doi.org/10.1002/chem.201701547
  27. Hitoshi Saito, Jieran Chen, Junpei Kuwabara, Takeshi Yasuda, Takaki Kanbara. Facile one-pot access to π-conjugated polymers via sequential bromination/direct arylation polycondensation. Polymer Chemistry 2017, 8 (19) , 3006-3012. https://doi.org/10.1039/C7PY00332C
  28. Florian Lombeck, Franziska Marx, Karen Strassel, Susanna Kunz, Caroline Lienert, Hartmut Komber, Richard Friend, Michael Sommer. To branch or not to branch: C–H selectivity of thiophene-based donor–acceptor–donor monomers in direct arylation polycondensation exemplified by PCDTBT. Polymer Chemistry 2017, 8 (32) , 4738-4745. https://doi.org/10.1039/C7PY00879A
  29. Masayuki Wakioka, Fumiyuki Ozawa. Development of Palladium-Catalyzed Direct Arylation Polymerization (DArP). Journal of Synthetic Organic Chemistry, Japan 2017, 75 (8) , 810-820. https://doi.org/10.5059/yukigoseikyokaishi.75.810

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