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

Jullien-Macchi, E; Allain, C; Alain-Rizzo, V; Dumas-Verdes, C; Galmiche, L; Audibert, JF; Desta, MB; Pansu, RB; Audebert, P NEW JOURNAL OF CHEMISTRY 2014, 38, 3401-3407.

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.

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Publication

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Paru le 24 mars 2014

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DOI: 10.1039/c4nj00192c