Curved Perylene Diimides Fused with Seven-Membered Rings

Keisuke Fujimoto, Seiichiro Izawa, Ayumu Takahashi, Toshiyasu Inuzuka, Kazutaka Sanada, Masami Sakamoto, Yasuo Nakayama, Masahiro Hiramoto, Masaki Takahashi

Research output: Contribution to journalArticlepeer-review

Abstract

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 π-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.

Original languageEnglish
Pages (from-to)690-695
Number of pages6
JournalChemistry - An Asian Journal
Volume16
Issue number6
DOIs
Publication statusPublished - 15 Mar 2021

Keywords

  • conformational flexibility
  • curved π-system
  • organic photovoltaics
  • perylene diimide
  • seven-membered ring

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