Regioselective photodimerization of cinnamic acids in water: Templation with cucurbiturils

Mahesh Pattabiraman, Lakshmi S. Kaanumalle, Arunkumar Natarajan, V. Ramamurthy

Research output: Contribution to journalArticle

75 Scopus citations

Abstract

Cinnamic acids upon irradiation in solution undergo geometric isomerization while dimerizing to different dimers in the crystalline state. Controlling the nature of the dimer formed upon irradiation remains a challenging task. We have aligned a variety of cinnamic acid molecules in a head-head fashion employing cucurbit[8]uril, a weakly water soluble host as a template. The water solubility of cucurbit[8]uril is enhanced by inclusion of water soluble cinnamic acids and positions the olefins in an arrangement that favors the formation of syn head-head cyclobutanes in near quantitative yields. This methodology works in both solid state as well as in aqueous solution. Irradiation of cinnamic acid complexes with γ-cyclodextrin has been carried out as a comparison. We find that while cucurbit[8]uril functions well both in solid state and aqueous solution, cyclodextrin works best as solid complexes only. Consistent with the postulated requirement of large cavities for templating olefins to dimerization, irradiation of complexes of cinnamic acid with cucurbit[7]uril resulted in only the corresponding cis isomers.

Original languageEnglish (US)
Pages (from-to)7605-7609
Number of pages5
JournalLangmuir
Volume22
Issue number18
DOIs
StatePublished - Aug 29 2006

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

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