[2.2]paracyclophane/dehydrobenzoannulene hybrids: transannular delocalization in open-circuited conjugated macrocycles.
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.
Boydston
A J
AJ
Department of Chemistry University of Oregon Eugene, OR 97403-1253, USA, Fax: (+1) 541-346-0487.
Bondarenko
L
L
Dix
I
I
Weakley
T J
TJ
Hopf
H
H
Haley
M M
MM
alkynes; annulenes; aromaticity; cyclophanes; macrocycles