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Issue 8, 2014
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New highly electrodeficient cationic fluorescent tetrazines: a step toward the strongest purely organic photooxidants

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Abstract

Strongly fluorescent electrodeficient tetrazines substituted with cationic heterocycles have been prepared. These compounds can be reversibly reduced at a high potential and consequently they are strong oxidants in the excited state. As a result of their very strong photooxidant character, their fluorescence is quenched in the presence of toluene, m-xylene, styrene and sometimes even benzene, through a photoinduced electron transfer reaction via a dynamic quenching mechanism. Beyond their photooxidizing properties, these new molecules have potential towards the realization of new fluorescence sensors. As an example, tetrazine 3 has been dispersed on silica particles and we have demonstrated that its fluorescence is quenched upon exposure to benzene vapors.

Graphical abstract: New highly electrodeficient cationic fluorescent tetrazines: a step toward the strongest purely organic photooxidants

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Article information


Submitted
07 Feb 2014
Accepted
24 Mar 2014
First published
24 Mar 2014

New J. Chem., 2014,38, 3401-3407
Article type
Paper

New highly electrodeficient cationic fluorescent tetrazines: a step toward the strongest purely organic photooxidants

E. Jullien-Macchi, C. Allain, V. Alain-Rizzo, C. Dumas-Verdes, L. Galmiche, J. Audibert, M. Berhe Desta, R. B. Pansu and P. Audebert, New J. Chem., 2014, 38, 3401
DOI: 10.1039/C4NJ00192C

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