Host-guest chemistry aids and abets a stereospecific photodimerization in the solid state

Dafni G. Amirsakis, Miguel A. Garcia-Garibay, Stuart J. Rowan, J. Fraser Stoddart, Andrew J P White, David J. Williams

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Abstract

A bis(dialkylammonium ion)-substituted stilbene derivative cocrystallizes with bisparaphenylene[34]crown-10 to form, in the solid state, a 2:2 host-guest complex wherein the stilbene double bonds are aligned with a relative geometry suitable for a stereospecific photochemical [2+2] cycloaddition. When irradiated with white light, this crystalline complex forms a single diastereoisomer of the corresponding cyclobutane derivative (see schematic presentation), the stereo-chemistry of which has been determined unambiguously in the solid state by X-ray crystallography to be syn-anti-syn.

Original languageEnglish
Pages (from-to)4256-4261
Number of pages6
JournalAngewandte Chemie - International Edition
Volume40
Issue number22
DOIs
Publication statusPublished - 2001 Nov 19
Externally publishedYes

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Keywords

  • Photochemistry
  • Pseudorotaxanes
  • Self-assembly
  • Solid-state reactions
  • Template synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Amirsakis, D. G., Garcia-Garibay, M. A., Rowan, S. J., Fraser Stoddart, J., White, A. J. P., & Williams, D. J. (2001). Host-guest chemistry aids and abets a stereospecific photodimerization in the solid state. Angewandte Chemie - International Edition, 40(22), 4256-4261. https://doi.org/10.1002/1521-3773(20011119)40:22<4256::AID-ANIE4256>3.0.CO;2-S