Flapping Peryleneimide as a Fluorogenic Dye with High Photostability and Strong Visible-Light Absorption

Angewandte Chemie
Shohei SaitoTahei Tahara

Abstract

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 an inherent fluorescence (FL) of peryleneimide moieties. However, the FL quantum yield is remarkably improved with a prolonged lifetime by 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).

References

Jan 7, 2010·Journal of the American Chemical Society·Joanna R SiekierzyckaAlbert M Brouwer
Feb 22, 2011·Chemical Communications : Chem Comm·Baoxiang GaoXinwu Ba
May 11, 2012·Angewandte Chemie·Daniel GörlFrank Würthner
Jul 19, 2012·Physical Chemistry Chemical Physics : PCCP·Marina K Kuimova
Jan 25, 2013·Nature Chemistry·Gražvydas LukinavičiusKai Johnsson
Jun 1, 2013·Journal of the American Chemical Society·Chunxue YuanShigehiro Yamaguchi
Jan 21, 2014·Nature Nanotechnology·James A HutchisonJohan Hofkens
May 12, 2015·Bioconjugate Chemistry·Pinaki SarderSamuel Achilefu
Aug 14, 2015·Chemical Reviews·Frank WürthnerDavid Schmidt
Dec 20, 2012·The Journal of Physical Chemistry Letters·Kelly M LeflerMichael R Wasielewski
Feb 19, 2016·Journal of the American Chemical Society·Stefka KaloyanovaKalina Peneva
Apr 30, 2016·Journal of Materials Chemistry. C, Materials for Optical and Electronic Devices·Mark A Haidekker, Emmanuel A Theodorakis
Jul 5, 2016·Nature Communications·Shohei SaitoShigehiro Yamaguchi
Sep 14, 2016·Angewandte Chemie·Oleksii NevskyiDominik Wöll
Jul 26, 2017·Journal of the American Chemical Society·Chenguang WangShigehiro Yamaguchi
Sep 14, 2017·Journal of the American Chemical Society·Frank C HendriksBert M Weckhuysen
Oct 19, 2017·Journal of the American Chemical Society·Masaki HadaR J Dwayne Miller
Nov 22, 2017·Accounts of Chemical Research·Yang LiuKhalid Salaita
May 12, 2018·Journal of the American Chemical Society·Takuya YamakadoShohei Saito
Mar 6, 2019·Journal of the American Chemical Society·Zhixuan ZhouPeter J Stang
Apr 6, 2019·Journal of the American Chemical Society·Jiachao XuXiaohong Fang
Jul 25, 2019·Angewandte Chemie·Deng-Gao ChenPi-Tai Chou

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Citations

Aug 28, 2021·Journal of the American Chemical Society·Yuma GotoShohei Saito
Oct 29, 2021·Physical Chemistry Chemical Physics : PCCP·Peter B Karadakov, Nicholas Preston
Dec 19, 2021·Chimia·Lea AssiesStefan Matile
Feb 3, 2022·Journal of the American Chemical Society·Takuya Yamakado, Shohei Saito

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