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Hybrid Corannulene–Perylene Dyes: Facile Synthesis and Optoelectronic Properties
Author(s) -
Lin Zhi,
Li Cheng,
Meng Dong,
Li Yan,
Wang Zhaohui
Publication year - 2016
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.201600490
Subject(s) - perylene , corannulene , materials science , solvatochromism , nanotechnology , photochemistry , optoelectronics , chemistry , organic chemistry , molecule
Considering the peculiar topology of corannulene and extraordinary optoelectronic properties of perylene dyes, a series of hybrid corannulene–perylene dyes, namely corannulene‐fused perylene‐3,4‐dicarboxylic acid monoimide (PMI) and corannulene‐fused perylene‐3,4,9,10‐tetracarboxylic acid diimides (PDIs), were efficiently synthesized by a Suzuki coupling (carbon–carbon bond formation) and subsequent oxidative cyclization and photocyclization, respectively. Single crystal packing demonstrates that the solid state of the corannulene‐fused PMI is arranged in back to back antiparallel dimers due to the strong dipole–dipole interactions. Integration of the corannulene unit to the perylene dyes along peri‐positions makes the absorption bathochromically‐shifted together with a much higher molar extinction coefficient, whereas integration of the corannulene unit to the perylene dyes along bay‐positions has a much broader absorption. Strong and broad absorption properties, strong electron‐accepting ability, and suitable LUMO levels close to that of [6,6]‐phenyl‐C 61 ‐butyric acid methyl ester (PCBM) make hybrid corannulene–perylene dyes promising electron‐acceptor materials for organic optoelectronic devices.