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J. Phys. Chem. A 110 (2006) 12971-12975
Donor-Acceptor-Donor Tetrazines Containing a Ferrocene Unit: Synthesis, Electrochemical and Spectroscopic Properties
Izabela Janowska 1, Fabien Miomandre 2, Gilles Clavier 2, Pierre Audebert 2, Janusz Zakrzewski 1, Khuyen Hoang Thi 3, Isabelle Ledoux-Rak 3
(2006)

Donor-acceptor-donor tetrazines containing ferrocene moieties and phenyl unit as a ð-bridge have been synthesized and characterized. UV-vis spectroscopic and cyclic voltamperometric results indicate sizable intramolecular charge transfer interactions in the ground state when the ferrocene is directly bound to the tetrazine. On the other hand, the results show reduction of the electron-donor strength of ferrocene moieties when there is a phenyl linkage. Both tetrazines display a high reduction potential. The role of ferrocenyl groups appear to be detrimental to maximize the cubic hyperpolarizability ç of tetrazines, as compared to purely organic groups such as thiophene. A possible explanation for this behavior may originate from metalto- ligand charge transfer processes.
1 :  Department of Organic Chemistry
University of Lodz
2 :  Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM)
CNRS : UMR8531 – École normale supérieure de Cachan - ENS Cachan
3 :  Laboratoire de Photonique Quantique et Moléculaire (LPQM)
CNRS : UMR8537 – École normale supérieure de Cachan - ENS Cachan
Physique/Physique/Chimie-Physique