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

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.