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A Joint Theoretical and Experimental Insight into the Electronic Structure of Chromophores Derived from 6 H ,12 H ‐5,11‐Methanodibenzo[ b , f ][1,5]diazocine
Author(s) -
Lemaur Vincent,
Cornil Jérôme,
Didier Delphine,
Mujawase Aline,
Sergeyev Sergey
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790216
Subject(s) - chemistry , delocalized electron , chromophore , lone pair , quantum chemical , electronic structure , electrophile , stereochemistry , acceptor , reactivity (psychology) , crystallography , computational chemistry , molecule , photochemistry , organic chemistry , medicine , alternative medicine , pathology , catalysis , physics , condensed matter physics
We report on the synthesis and electronic spectra of the chiral, donor‐acceptor (push‐pull) chromophores (±)‐ 4 and (±)‐ 5 with a 6 H ,12 H ‐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 6 H ,12 H ‐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 delocalization of the lone pair of the bridge‐head N‐atoms in this heterocyclic system.