化学
量子产额
斯托克斯位移
荧光
光化学
分子内力
取代基
氢键
质子化
生命科学中的荧光
发色团
吸收(声学)
荧光团
激发态
立体化学
分子
有机化学
原子物理学
物理
量子力学
离子
声学
作者
Ervin Kovács,Levente Cseri,Attila Jancsó,Ferenc Terényi,Anna Fülöp,Balázs Rózsa,Gábor Galbács,Zoltán Mucsi
标识
DOI:10.1002/ejoc.202101173
摘要
Abstract Novel small‐molecular analogues the green fluorescence protein (GFP) chromophore were synthesised to expand and improve this fluorophore family and to deepen the understanding of their fluorescence mechanism. The introduction of an aminophenyl substituent and the repositioning of the hydroxyl group, to enable strong intramolecular hydrogen bonding, not only enhanced fluorescence emission but also resulted in an increased Stokes shift and a considerable redshift. Experimental and computational results described dual fluorescence involving both excited‐state intramolecular proton transfer and internal charge transfer (ESIPT‐ICT) mechanisms. Screening of the pH and the solvent medium revealed a complicated equilibrium involving hydrogen bonding, protonation and deprotonation that influences the absorption and emission spectra. Further improvement of the photophysical properties via the systematic variation of dialkylamino substituents at a single position of the chromophore led to a two‐orders of magnitude enhancement in the quantum yields. In addition, the novel compounds also have significant two‐photon absorption, which widens the possibilities for applications in the field of bioimaging.
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