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Flapping Peryleneimide as a Fluorogenic Dye with High Photostability and Strong Visible‐Light Absorption
Author(s) -
Kimura Ryo,
Kuramochi Hikaru,
Liu Pengpeng,
Yamakado Takuya,
Osuka Atsuhiro,
Tahara Tahei,
Saito Shohei
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202006198
Subject(s) - chemical mechanical planarization , absorption (acoustics) , quenching (fluorescence) , flapping , quantum yield , photochemistry , fluorescence , materials science , visible spectrum , chemistry , optoelectronics , nanotechnology , optics , physics , thermodynamics , layer (electronics) , wing , composite material
Flapping fluorophores (FLAP) with a flexible 8π ring are rapidly gaining attention as a versatile photofunctional system. Here we report a highly photostable “flapping peryleneimide” with an unprecedented fluorogenic mechanism based on a bent‐to‐planar conformational change in the S 1 excited state. The S 1 planarization induces an electronic configurational switch, almost quenching the inherent fluorescence (FL) of the peryleneimide moieties. However, the FL quantum yield is remarkably improved with a prolonged lifetime upon a slight environmental change. This fluorogenic function is realized by sensitive π‐conjugation design, as a more π‐expanded analogue does not show the planarization dynamics. With strong visible‐light absorption, the FL lifetime response synchronized with the flexible flapping motion is useful for the latest optical techniques such as FL lifetime imaging microscopy (FLIM).