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The [2](1,4)Anthraceno[2](2,6)pyridinophan-1,13-dien (5) and the corresponding [2.2]phane (7) were synthesized as models for exciplexes. The dithia[3.3]phanes(9) and (11) were prepared by cyclisation of the dithiols 13 and 16 with the dibromide 19. Oxidation of 9 to the disulfone 10 and vapour phase pyrolysis led to 7. Ring contraction of 9 by S-analogous Wittig ether rearrangement led to 20 which was converted to the diene 5 via oxidation to the disulfoxide 21 and pyrolytic elimination of methane sulfenic acid. Attempts to prepare 6 and 8 via similar routes from 11 failed. Electron absorption spectra and fluorescence spectra of 5 and 7 are discussed in terms of n-π interaction in 5 and π-π interaction in 7.

zeitschrift für naturforschung b

Transanulare Wechselwirkung bei [m.n]Phanen, 32 [1]: Modelle für Amin-Aromaten-Exciplexe: [2](1,4)Anthraceno[2](2,6)pyridinophan-1,13-dien/Transanular Interaction in [m .n]Phanes, 32 [1]: Models for Amine-Arene-Exciplexes: [2](1,4)Anthraceno[2](2,6)pyridinophan-1,13-dien