Naphthoxazole-based singlet oxygen fluorescent probes

Rubén Ruiz-González, Renzo Zanocco, Yasser Gidi, Antonio L. Zanocco, Santi Nonell, Else Lemp

Research output: Indexed journal article Articlepeer-review

29 Citations (Scopus)

Abstract

In this study, we report the synthesis and photochemical behavior of a new family of photoactive compounds to assess its potential as singlet oxygen ( 1O2) probes. The candidate dyads are composed by a 1O2 trap plus a naphthoxazole moiety linked directly or through an unsaturated bond to the oxazole ring. In the native state, the inherent great fluorescence of the naphthoxazole moiety is quenched; but in the presence of 1O2, generated by the addition and appropriate irradiation of an external photosensitizer, a photooxidation reaction occurs leading to the formation of a new chemical entity whose fluorescence is two orders of magnitude higher than that of the initial compound, at the optimal selected wavelength. The presented dyads outperform the commonly used indirect fluorescent 1O2 probes in terms of fluorescence enhancement maintaining the required specificity for 1O2 detection in solution.

Original languageEnglish
Pages (from-to)1427-1432
Number of pages6
JournalPhotochemistry and Photobiology
Volume89
Issue number6
DOIs
Publication statusPublished - Nov 2013

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