Asymmetric photoreaction under high pressure - Pressure control of product chirality

Masayuki Kaneda, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalReview articlepeer-review

Abstract

Pressure effects upon asymmetric photochemical reactions are discussed in the context of entropy control of these reactions. In the enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) to chiral (E)-isomer (1E) sensitized by chiral aromatic esters (2-7), the 1E/1Z ratio and the enantiomeric excess (ee) of 1E are critical functions of the applied pressure, accompanying an unprecedented switching of the product chirality. Furthermore, the differential activation parameters (ΔΔΙ, δδΙ and ΔΔV†) obtained by changing pressure and temperature clearly indicate that these variants act as independent factors in the enantiodifferentiating process. This opens a new channel to the multidimensional control of not only asymmetric photochemical but also conventional thermo/photo/biochemical reactions in which weak interactions are the principal driving force or determining factor.

Original languageEnglish
Pages (from-to)227-233
Number of pages7
JournalReview of High Pressure Science and Technology/Koatsuryoku No Kagaku To Gijutsu
Volume11
Issue number3
DOIs
Publication statusPublished - 2001
Externally publishedYes

Keywords

  • Asymmetric photochemistry
  • Enantiodifferentiation
  • Exciplex
  • Multidimensional control
  • Photosensitization
  • Pressure effect
  • Temperature effect

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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