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BODIPY‐Tetrazine Multichromophoric Derivatives
Author(s) -
DumasVerdes Cécile,
Miomandre Fabien,
Lépicier Eve,
Galangau Olivier,
Vu Thanh Truc,
Clavier Gilles,
MéalletRenault Rachel,
Audebert Pierre
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900874
Subject(s) - tetrazine , bodipy , chemistry , photochemistry , moiety , fluorescence , absorption (acoustics) , fluorophore , electrochemistry , electron transfer , organic chemistry , materials science , electrode , physics , quantum mechanics , composite material
New dyes based on BODIPY and tetrazine fluorophores connected through a phenyl spacer have been synthesized and their absorption, emission and electrochemical properties characterized. BODIPY can be reversibly oxidized into a stable cation radical whereas tetrazine can be reduced to a stable anion radical. The electrochemical and absorption studies demonstrate that both fluorophores behave independently. The bichromophoric compounds show an expected very weak emission by the BODIPY core that is quenched by the phenoxytetrazine mainly through energy transfer. DFT calculations and spectroelectrochemistry experiments demonstrate that photoinduced electron transfer and energy transfer remain possible when the tetrazine moiety is reduced electrochemically, which prevents switching on of the fluorescence of the BODIPY unit.