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
JYU authors or editors
Publication details
All authors or editors: Tervola, Essi; Truong, Khai-Nghi; Ward, Jas S; Priimagi, Arri; Rissanen, Kari
Journal or series: RSC Advances
eISSN: 2046-2069
Publication year: 2020
Volume: 10
Pages range: 29385-29393
Publisher: Royal Society of Chemistry (RSC)
Publication country: United Kingdom
Publication language: English
DOI: https://doi.org/10.1039/d0ra04691d
Publication open access: Openly available
Publication channel open access: Open 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.
Keywords: fluorescence; aromatic compounds
Free keywords: fluorescence enhancement; protonation
Contributing organizations
Related projects
- Haloniumsupramolecular Chemistry: New Molecular Machines and Nanoreactors
- Rissanen, Kari
- Research Council of Finland
Ministry reporting: Yes
Reporting Year: 2020
JUFO rating: 1