Highly efficient cucurbit[8]uril-templated intramolecular photocycloaddition of 2-naphthalene-labeled poly(ethylene glycol) in aqueous solution

J Org Chem. 2008 Jan 18;73(2):491-4. doi: 10.1021/jo701998e. Epub 2007 Dec 23.

Abstract

The photodimerization of water-insoluble 2-naphthalene-labeled poly(ethyl glycol) (N-Pn-N) in cucurbit[8]uril (CB[8]) aqueous solution was investigated. UV-vis, fluorescence, and 1H NMR analysis reveal that CB[8] can encapsulate N-Pn-N to make a stable 1:1 inclusion complex N-Pn-N@CB[8] in aqueous solution. Irradiation of N-Pn-N in the CB[8] aqueous solution results in intramolecular photocycloaddition with remarkable selectivity and efficiency, whereas no photodimer could be detected in host-free solution.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged-Ring Compounds / chemistry
  • Bridged-Ring Compounds / radiation effects*
  • Cyclization
  • Dimerization
  • Imidazoles / chemistry
  • Imidazoles / radiation effects*
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / radiation effects*
  • Photochemistry
  • Polyethylene Glycols / chemistry
  • Polyethylene Glycols / radiation effects*
  • Solutions / chemistry
  • Solutions / radiation effects
  • Spectrometry, Fluorescence
  • Ultraviolet Rays*
  • Water / chemistry

Substances

  • Bridged-Ring Compounds
  • Imidazoles
  • Naphthalenes
  • Solutions
  • cucurbit(8)uril
  • Water
  • naphthalene
  • Polyethylene Glycols