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Audebert P, Miomandre F, Clavier G, et al. Synthesis and properties of new tetrazines substituted by heteroatoms: towards the world's smallest organic fluorophores. Chemistry. 2005;11(19):5667-73doi: 10.1002/chem.200401252.
Audebert, P., Miomandre, F., Clavier, G., Vernières, M. C., Badré, S., & Méallet-Renault, R. (2005). Synthesis and properties of new tetrazines substituted by heteroatoms: towards the world's smallest organic fluorophores. Chemistry (Weinheim an der Bergstrasse, Germany), 11(19), 5667-73. https://doi.org/10.1002/chem.200401252
Audebert, Pierre, et al. "Synthesis and properties of new tetrazines substituted by heteroatoms: towards the world's smallest organic fluorophores." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 11,19 (2005): 5667-73. doi: https://doi.org/10.1002/chem.200401252
Audebert P, Miomandre F, Clavier G, Vernières MC, Badré S, Méallet-Renault R. Synthesis and properties of new tetrazines substituted by heteroatoms: towards the world's smallest organic fluorophores. Chemistry. 2005 Sep 19;11(19):5667-73. doi: 10.1002/chem.200401252. PMID: 16021645.
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Chemistry. 2005 Sep 19;11(19):5667-73. doi: 10.1002/chem.200401252.

Synthesis and properties of new tetrazines substituted by heteroatoms: towards the world's smallest organic fluorophores.

Chemistry (Weinheim an der Bergstrasse, Germany)

Pierre Audebert, Fabien Miomandre, Gilles Clavier, Marie-Claude Vernières, Sophie Badré, Rachel Méallet-Renault

Affiliations

  1. Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires, UMR 8531, Ecole Normale Supérieure de Cachan, 61 Av. du Pt Wilson, 94235 Cachan, France. [email protected]

PMID: 16021645 DOI: 10.1002/chem.200401252

Abstract

New tetrazines substituted by heteroatoms have been synthesized and their electrochemical and photochemical properties investigated. All compounds are reversibly electroactive with standard potentials shifting cathodically according to the donor character of the substituent. The tetrazine derivatives are also fluorescent with maximum emission wavelengths in the range 550-575 nm. Some of them show very long fluorescence lifetimes (several tens of ns) and remain fluorescent in the solid state without major changes in the spectral features. The fluorescence of one of the derivatives can be efficiently quenched by the presence of electron-rich compounds such as triphenylamines, phenol or anisole, which make them very promising compounds for sensor applications.

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