Impact of Hydrogen Bonding on the Fluorescence of N-Amidinated Fluoroquinolones.

Autor: Xie S; Department of Chemistry, KTH-Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden.; College of Chemistry and Chemical Engineering, Hunan University, 410082, Changsha, China., Manuguri S; Department of Chemistry, KTH-Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden., Ramström O; Department of Chemistry, KTH-Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden.; Department of Chemistry, University of Massachusetts Lowell, 1 University Ave., Lowell, MA, 01854, USA.; Department of Chemistry and Biomedical Sciences, Linnaeus University, 39182, Kalmar, Sweden., Yan M; Department of Chemistry, KTH-Royal Institute of Technology, Teknikringen 30, 10044, Stockholm, Sweden.; Department of Chemistry, University of Massachusetts Lowell, 1 University Ave., Lowell, MA, 01854, USA.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2019 Mar 15; Vol. 14 (6), pp. 910-916. Date of Electronic Publication: 2019 Feb 27.
DOI: 10.1002/asia.201801916
Abstrakt: The fluorescence properties of AIE-active N-amidinated fluoroquinolones, efficiently obtained by a perfluoroaryl azide-aldehyde-amine reaction, have been studied. The fluorophores were discovered to elicit a highly sensitive fluorescence quenching response towards guest molecules with hydrogen-bond-donating ability. This effect was evaluated in a range of protic/aprotic solvents with different H-bonding capabilities, and also in aqueous media. The influence of acid/base was furthermore addressed. The hydrogen-bonding interactions were studied by IR, NMR, UV/Vis and time-resolved fluorescence decay, revealing their roles in quenching of the fluorescence emission. Due to the pronounced quenching property of water, the N-amidinated fluoroquinolones could be utilized as fluorescent probes for quantifying trace amount of water in organic solvents.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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