Modelle für Amin-Aromaten-Exciplexe: [2](1,4)Anthraceno[2](2,6)pyridinophan-1,13-dien (Transanulare Wechselwirkung bei [m.n]Phanen ; 32)

Abstract

The [2](1,4)Anthraceno[2](2.6)pyridinophan-1,13-dien and the corresponding [2,2]phane were synthesized as models for exciplexes. The dithia[3,3]phanes and were prepared by cyclisation of the dithiols 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.