High CT-Fluorophore Featuring a Basic Moiety into D-A Chain as a p Probe.

J Org Chem

Grupo de Química Orgánica Medicinal, Instituto de Química Biológica, Facultad de Ciencias, Universidad de la República, Iguá 4225, 11400 Montevideo, Uruguay.

Published: June 2022

AI Article Synopsis

  • The study addresses the difficulty in measuring acidity using fluorometry, as traditional methods often overestimate acidity due to excitation effects.
  • The researchers developed a novel p probe, -aryl-7-methoxy-2-(trifluoromethyl)benzo[][1,8]naphthyridin-4(1)-one, which provides a linear log p correlation by selectively responding to different Brønsted acids.
  • Key features of the probe include a weak basic component that enhances quenching related to acidity and a broad p range (19.5p) for accurate measurements, paving the way for more effective fluorescent p probes in the future.

Article Abstract

The determination of acidity represents a significant challenge within fluorometry, and no effective strategy has been developed successfully yet. It is attributed to the fact that acidity tends to be enhanced upon excitation, giving, in general, an overestimation of the ionization constant, p. Herein, we developed a strategy for p estimation of Brønsted acids in solution through fluorometry by using a convenient p probe, -aryl-7-methoxy-2-(trifluoromethyl)benzo[][1,8]naphthyridin-4(1)-one. It allowed us to obtain a linear log p correlation derived from the selective quenching response of the probe by an interaction with different Brønsted acids. The key points of -aryl-7-methoxy-2-(trifluoromethyl)benzo[][1,8]naphthyridin-4(1)-one as a p probe were (i) the location of a weak basic moiety in the donor-acceptor chain of the fluorophore, which favors a selective quenching of the intramolecular charge-transfer process according to the acidity of acid, and (ii) the high CT character upon excitation that promotes higher quenching magnitudes and favors a wider p range (19.5p) for the log p correlation. Other key principles were to delimit the study to pure proton transfer and nonfluorescent acids, which allowed restricting the quenching response to a process dependent mainly on the acid-base equilibrium. All these findings open a new perspective as a proof of concept to design effective fluorescent p probes.

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http://dx.doi.org/10.1021/acs.joc.1c03104DOI Listing

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