Synthesis and Fluorescence Mechanism of the Aminoimidazolone Analogues of the Green Fluorescent Protein Towards Advanced Dyes with Enhanced Stokes Shift, Quantum Yield and Two-Photon Absorption /

Novel small-molecular analogues the green fluorescence protein (GFP) chromophore are 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 t...

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Elmentve itt :
Bibliográfiai részletek
Szerzők: Kovács Ervin
Cseri Levente
Jancsó Attila
Terényi Ferenc
Fülöp Anna
Rózsa J. Balázs
Galbács Gábor
Mucsi Zoltán
Dokumentumtípus: Cikk
Megjelent: 2021
Sorozat:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2021 No. 41
Tárgyszavak:
doi:10.1002/ejoc.202101173

mtmt:32399352
Online Access:http://publicatio.bibl.u-szeged.hu/23508
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520 3 |a Novel small-molecular analogues the green fluorescence protein (GFP) chromophore are 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 enhances fluorescence emission, but also results in an increased Stokes shift and a considerable red shift. Experimental and computational results describe a dual fluorescence involving both excited-state intramolecular proton transfer and internal charge transfer (ESIPT?ICT) mechanism. The 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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700 0 1 |a Jancsó Attila  |e aut 
700 0 1 |a Terényi Ferenc  |e aut 
700 0 1 |a Fülöp Anna  |e aut 
700 0 2 |a Rózsa J. Balázs  |e aut 
700 0 2 |a Galbács Gábor  |e aut 
700 0 2 |a Mucsi Zoltán  |e aut 
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