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Curved Perylene Diimides Fused with Seven‐Membered Rings
Author(s) -
Fujimoto Keisuke,
Izawa Seiichiro,
Takahashi Ayumu,
Inuzuka Toshiyasu,
Sanada Kazutaka,
Sakamoto Masami,
Nakayama Yasuo,
Hiramoto Masahiro,
Takahashi Masaki
Publication year - 2021
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202100066
Subject(s) - perylene , diimide , regioselectivity , intramolecular force , photochemistry , materials science , chemistry , molecule , stereochemistry , organic chemistry , catalysis
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.