Templating photodimerization of trans-cinnamic acid esters with a water-soluble Pd nanocage

S. Karthikeyan, V. Ramamurthy

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Abstract

A water-soluble octahedral Pd nanocage acting as a reaction vessel templates the photodimerization of substituted trans-cinnamic acid methyl esters in water. Irradiation of the host-guest complexes of trans-cinnamic acid methyl esters with the Pd nanocage resulted in selective formation of a syn head-head dimer in addition to the corresponding cis isomer. These results suggest that the guest molecules are preoriented in a selective fashion with the hydrophilic ester group facing water and the hydrophobic aryl group tucked within the cavity of the host. Such an orientation occurs at the hydrophobic-hydrophilic interface between the nanocage exterior and interior. Weak intermolecular C-H-π and π-π interactions between the host and the guest(s) are likely to be responsible for the lack of mobility of the reactant olefins during their short excited-state lifetime.

Original languageEnglish (US)
Pages (from-to)452-458
Number of pages7
JournalJournal of Organic Chemistry
Volume72
Issue number2
DOIs
StatePublished - Jan 19 2007

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ASJC Scopus subject areas

  • Organic Chemistry

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