[2.2]Paracyclophane/Dehydrobenzoannulene Hybrids: Transannular Delocalization in Open-Circuited Conjugated Macrocycles

✍ Scribed by A. J. Boydston; Lidija Bondarenko; Ina Dix; Timothy J. R. Weakley; Henning Hopf; Michael M. Haley

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 110 KB
• Volume: 40
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/1521-3773(20010817)40:16<2986::aid-anie2986>3.0.co;2-i

✦ Synopsis

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.