2019
DOI: 10.1002/asia.201801916
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Impact of Hydrogen Bonding on the Fluorescence of N‐Amidinated Fluoroquinolones

Abstract: 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‐… Show more

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Cited by 19 publications
(16 citation statements)
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“…These nanoaggregates, made entirely of the drug molecules, showed enhanced antimicrobial activities compared with the simple molecule. The covalent functionalization furthermore turns on the otherwise weak fluorescence of ciprofloxacin. , The amidine product becomes strongly emissive upon aggregation, whereas its homogeneous solution is weakly fluorescent as a result of intramolecular charge transfer quenching. This example represents a novel approach to theranostic nanodrugs.…”
Section: Reactions Of Pfaas With Electron-rich Dipolarophilesmentioning
confidence: 99%
“…These nanoaggregates, made entirely of the drug molecules, showed enhanced antimicrobial activities compared with the simple molecule. The covalent functionalization furthermore turns on the otherwise weak fluorescence of ciprofloxacin. , The amidine product becomes strongly emissive upon aggregation, whereas its homogeneous solution is weakly fluorescent as a result of intramolecular charge transfer quenching. This example represents a novel approach to theranostic nanodrugs.…”
Section: Reactions Of Pfaas With Electron-rich Dipolarophilesmentioning
confidence: 99%
“…These H-bonds can in turn induce non-radiative pathways, by competing with the radiative ICT processes between the BTZ and quinolinol moieties. 30 To further demonstrate this point, when D 2 O was used instead of H 2 O for the solutions with f w of 50%, their fluorescence was enhanced, increasing their PLQYs for the DMSO and TFA solutions by 22 and 29%, respectively. A striking difference was seen in the TFA spectra, where the weaker ICT/AIE peak became more intense than the monomeric peak while also getting broader and bathochromically shifted to 462 nm ( Fig.…”
Section: Resultsmentioning
confidence: 94%
“…In spite of this, no AIE peak emerged, which can be explained by TFAs ability to form strong intermolecular H-bonds between the phenolic and pyridinium moieties of compound 5H 2 2+ , as seen by the crystal structure. These H-bonds can in turn induce nonradiative pathways, by competing with the radiative ICT processes between the BTZ and quinolinol moieties 30. To further demonstrate this point, when D 2 O was used instead of H 2 O for the solutions with f w of 50%, their uorescence was enhanced, increasing their PLQYs for the DMSO and TFA solutions by 22 and 29%, respectively.…”
mentioning
confidence: 92%
“…In contrast to CPF-hex, Bis-b exhibits the aggregation-induced emission enhancement effect in its solid state. This phenomenon is presented in detail in [ 36 ]. Autofluorescence of polymer scaffolds allows studying their further biodegradation in vivo without the need of developing complicated histological procedures and sacrificing experimental animals [ 21 ].…”
Section: Resultsmentioning
confidence: 99%