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Impact of Hydrogen Bonding on the Fluorescence of N-Amidinated Fluoroquinolones
KTH Royal Instute of Technology, Sweden;Hunan Univ, Peoples Republic of China.
KTH Royal Instute of Technology, Sweden.ORCID iD: 0000-0001-7784-2431
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. KTH Royal Instute of Technology, Sweden;Univ Massachusetts, USA.
KTH Royal Instute of Technology, Sweden;Univ Massachusetts, USA.ORCID iD: 0000-0003-1121-4007
2019 (English)In: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 14, no 6, p. 910-916Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
Wiley-Blackwell, 2019. Vol. 14, no 6, p. 910-916
Keywords [en]
aggregation-induced emission, fluorescence quenching, fluoroquinolones, hydrogen bonds, water sensors
National Category
Chemical Sciences
Research subject
Natural Science, Chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-81699DOI: 10.1002/asia.201801916ISI: 000461836500032PubMedID: 30762939Scopus ID: 2-s2.0-85062327816OAI: oai:DiVA.org:lnu-81699DiVA, id: diva2:1302773
Available from: 2019-04-05 Created: 2019-04-05 Last updated: 2019-08-29Bibliographically approved

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Ramström, Olof

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