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A joint theoretical and experimental insight into the electronic structure of chromophores derived from 6H,12H-5,11-methano-dibenzo[b,f][1,5]diazocine

par Lemaur, Vincent;Cornil, Jérôme ;Didier, Delphine ;Mujawase, Aline;Sergueev, Serguei
Référence Helvetica chimica acta, 90, 11, page (2087-2095)
Publication Publié, 2007

Article révisé par les pairs

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Résumé :

We report on the synthesis and electronic spectra of the chiral, donor-acceptor (push-pull) chromophores (±)-4 and (±)-5 with a 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine scaffold (Scheme 1 and Fig. 2). The electronic structures of these compounds were investigated at a quantum-chemical level (Figs. 2 and 3). The chemical reactivity of 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine ((±)-11) towards aromatic electrophilic substitution (Scheme 2 and Table) provided additional information about its electronic structure and confirmed nonnegligible derealization of the lone pair of the bridge-head N-atoms in this heterocyclic system. © 2007 Verlag Helvetica Chimica Acta AG.