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- Title
Curved Perylene Diimides Fused with Seven‐Membered Rings.
- Authors
Fujimoto, Keisuke; Izawa, Seiichiro; Takahashi, Ayumu; Inuzuka, Toshiyasu; Sanada, Kazutaka; Sakamoto, Masami; Nakayama, Yasuo; Hiramoto, Masahiro; Takahashi, Masaki
- 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.
- Subjects
PERYLENE; NUCLEAR magnetic resonance spectroscopy; MOLECULAR structure; IMIDES; PHOTOELECTRICITY
- Publication
Chemistry - An Asian Journal, 2021, Vol 16, Issue 6, p690
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.202100066