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Impact of Hydrogen Bonding on the Fluorescence of N-Amidinated Fluoroquinolone
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, United States.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, United States.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-VCH Verlagsgesellschaft, 2019. Vol. 14, no 6, p. 910-916
Keywords [en]
aggregation-induced emission, fluorescence quenching, fluoroquinolones, hydrogen bonds, water sensors
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-248338DOI: 10.1002/asia.201801916ISI: 000461836500032PubMedID: 30762939Scopus ID: 2-s2.0-85062327816OAI: oai:DiVA.org:kth-248338DiVA, id: diva2:1302986
Note

QC 20190408

Available from: 2019-04-08 Created: 2019-04-08 Last updated: 2019-04-08Bibliographically approved

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Xie, ShengRamström, OlofYan, Mingdi

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