期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 16, 期 6, 页码 690-695出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202100066
关键词
curved π -system; seven-membered ring; perylene diimide; conformational flexibility; organic photovoltaics
资金
- Nanotechnology Platform Program (Molecule and Material Synthesis), JSPS KAKENHI of the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan [18K14115, 19K15536]
- Toukai Foundation for Technology
- Mazda foundation
- Kao Foundation for Arts and Sciences
- Grants-in-Aid for Scientific Research [19K15536, 18K14115] Funding Source: KAKEN
Synthesis of curved perylene diimides fused with seven-membered rings using regioselective bay-functionalization method and Pd-catalyzed intramolecular C-H/C-Br coupling reaction was achieved. X-Ray analysis and temperature-dependent NMR spectroscopy confirmed the curved molecular structure with conformational flexibility. The introduction of curved structure enabled removal of bulky N-substituents, enhancing solubility and power conversion efficiency in organic photovoltaic devices.
Curved perylene diimides fused with seven-membered rings have been synthesized using a regioselective bay-functionalization method and Pd-catalyzed intramolecular C-H/C-Br coupling reaction. X-Ray analysis and temperature-dependent NMR spectroscopy revealed the curved molecular structure with a certain degree of conformational flexibility. The curved and expanded pi-conjugation altered the electronic properties while retaining the intrinsic properties of the parent perylene diimide. Despite the absence of solubilizing N-substituents, the curved perylene diimides showed sufficient solubility for application in solution-processed organic photovoltaic devices. The devices showed superior performance with a power conversion efficiency of up to 2.76% due to suppressed charge recombination. Our detailed investigations suggest that the introduction of a curved structure enables the removal of the bulky N-substituents, which is an effective way to achieve a thin-film morphology suitable for photoelectric conversion.
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