A1 Journal article (refereed)
Fluorescence enhancement of quinolines by protonation (2020)


Tervola, E., Truong, K.-N., Ward, J. S., Priimagi, A., & Rissanen, K. (2020). Fluorescence enhancement of quinolines by protonation. RSC Advances, 10, 29385-29393. https://doi.org/10.1039/d0ra04691d


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Publication details

All authors or editorsTervola, Essi; Truong, Khai-Nghi; Ward, Jas S; Priimagi, Arri; Rissanen, Kari

Journal or seriesRSC Advances

eISSN2046-2069

Publication year2020

Volume10

Pages range29385-29393

PublisherRoyal Society of Chemistry (RSC)

Publication countryUnited Kingdom

Publication languageEnglish

DOIhttps://doi.org/10.1039/d0ra04691d

Publication open accessOpenly available

Publication channel open accessOpen Access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/71433


Abstract

A study of the fluorescence enhancement of isoquinoline, acridine (benzo[b]quinoline) and benzo[h]quinoline is reported with six organic acids of different pKa values. Protonation was found to be an effective tool in the fluorescence enhancement of quinolines. A significant increase in the fluorescence intensity is observed only when strong acids are used, resulting in an over 50-fold increase in fluorescence with trifluoroacetic or benzenesulfonic acid and isoquinoline in a 1.5 : 1 ratio. The benzenesulfonic acid was found to be the most effective in the protonation of the bases despite its higher pKa value compared to trifluoro- and trichloroacetic acid. The X-ray crystal structures of 14 salts reveal the charge-assisted hydrogen bond O⋯N distances to vary very little, from 2.560(2)–2.714(3) Å, with the exception of the isoquinolinium benzenesulfonate where the O⋯N distance of 2.862(7) Å is caused by additional intermolecular interactions in the solid-state.


Keywordsfluorescencearomatic compounds

Free keywordsfluorescence enhancement; protonation


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Ministry reportingYes

Reporting Year2020

JUFO rating1


Last updated on 2024-26-03 at 09:19