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[2.2]paracyclophane/dehydrobenzoannulene hybrids: transannular delocalization in open-circuited conjugated
A J Boydston1, L Bondarenko, I Dix
1Department of Chemistry University of Oregon Eugene, OR 97403-1253, USA, Fax: (+1) 541-346-0487.
Angewandte Chemie (International Ed. in English)
|August 31, 2002
Abstract:
Enhanced global delocalization throughout the "stepped" π-electron systems of the [2.2]paracyclophane/dehydrobenzoannulene (PC/DBA) hybrids 1 and 2 is strongly suggested by a comparison of their electronic absorption spectra with those of model compounds with complete and interrupted classical aromatic delocalization. A distinct bathochromic shift (for 1) and greater absorption intensity at higher wavelengths (for 1 and 2) is observed versus the corresponding model hydrocarbons.