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Naphthoxazole‐Based Singlet Oxygen Fluorescent Probes
Author(s) -
RuizGonzález Rubén,
Zanocco Renzo,
Gidi Yasser,
Zanocco Antonio L.,
ll Santi,
Lemp Else
Publication year - 2013
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/php.12106
Subject(s) - photochemistry , moiety , singlet oxygen , fluorescence , photosensitizer , chemistry , bodipy , oxazole , singlet state , oxygen , excited state , stereochemistry , organic chemistry , optics , physics , nuclear physics
In this study, we report the synthesis and photochemical behavior of a new family of photoactive compounds to assess its potential as singlet oxygen ( 1 O 2 ) probes. The candidate dyads are composed by a 1 O 2 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 1 O 2 , 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 1 O 2 probes in terms of fluorescence enhancement maintaining the required specificity for 1 O 2 detection in solution.