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

S. Karthikeyan, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

52 Citations (Scopus)

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

Fingerprint

Esters
Water
Alkenes
Excited states
Isomers
Dimers
Irradiation
Molecules
cinnamic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Templating photodimerization of trans-cinnamic acid esters with a water-soluble Pd nanocage. / Karthikeyan, S.; Ramamurthy, Vaidhyanathan.

In: Journal of Organic Chemistry, Vol. 72, No. 2, 19.01.2007, p. 452-458.

Research output: Contribution to journalArticle

@article{c4abfcc21b834dbaa5c8810355f494c9,
title = "Templating photodimerization of trans-cinnamic acid esters with a water-soluble Pd nanocage",
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.",
author = "S. Karthikeyan and Vaidhyanathan Ramamurthy",
year = "2007",
month = "1",
day = "19",
doi = "10.1021/jo0617722",
language = "English",
volume = "72",
pages = "452--458",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "2",

}

TY - JOUR

T1 - Templating photodimerization of trans-cinnamic acid esters with a water-soluble Pd nanocage

AU - Karthikeyan, S.

AU - Ramamurthy, Vaidhyanathan

PY - 2007/1/19

Y1 - 2007/1/19

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=33846189436&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33846189436&partnerID=8YFLogxK

U2 - 10.1021/jo0617722

DO - 10.1021/jo0617722

M3 - Article

C2 - 17221961

AN - SCOPUS:33846189436

VL - 72

SP - 452

EP - 458

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 2

ER -