Diastereospecific photochemical dimerization of a stilbene-containing daisy chain monomer in solution as well as in the solid state

Dafni G. Amirsakis, Arkadij M. Elizarov, Miguel A. Garcia-Garibay*, Peter T. Glink, J. Fraser Stoddart, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

74 Scopus citations

Abstract

A crown ether/dialkylammonium ion hybrid containing a stilbene group self-assembles into a [c2]daisy chain-like pseudorotaxane, the solid-state superstructure of which was confirmed by X-ray crystallography. Upon irradiation, the pseudorotaxane undergoes an efficient photochemical [2+2] dimerization, both in solution as well as in the solid state, to yield one cyclobutane diastereoisomer with syn-anti-syn stereochemistry and head-to-tail regiochemistry (see scheme).

Original languageEnglish (US)
Pages (from-to)1126-1132
Number of pages7
JournalAngewandte Chemie - International Edition
Volume42
Issue number10
DOIs
StatePublished - Mar 10 2003

Keywords

  • Dimerization
  • Photochemistry
  • Pseudorotaxane solid-state reactions
  • Structure-directed synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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