Cyclophanes Containing Bowl-Shaped Aromatic Chromophores: Three Isomers of anti-[2.2](1,4)Subphthalocyaninophane

Quan Liu, Soji Shimizu, Nagao Kobayashi

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The connection of bowl-shaped aromatic boron subphthalocyanines with anti-[2.2]paracyclophane resulted in the first observation of electronic communication between convex and concave surfaces. Three isomers of anti-[2.2](1,4)subphthalocyaninophane, described as concave - concave (CC), convex - concave (CV), and convex - convex (VV) according to the orientation of the subphthalocyanine units, were synthesized and characterized by various spectroscopic techniques, including 1H NMR, electronic absorption, fluorescence, and magnetic circular dichroism spectroscopy and X-ray crystallography, together with molecular-orbital calculations. On going from the CC system to CV and further to VV, the Q band broadened and finally split as a result of through-space expansion of the conjugated systems, which were also reproduced theoretically.

Original languageEnglish
Pages (from-to)5187-5191
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number17
DOIs
Publication statusPublished - 2015 Apr 20

Keywords

  • cyclophanes
  • ring-current effects
  • subphthalocyanines
  • transannular interactions
  • π conjugation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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