Catalytically active supramolecular porphyrin boxes

Acceleration of the methanolysis of phosphate triesters via a combination of increased local nucleophilicity and reactant encapsulation

Byungman Kang, Josh W. Kurutz, Kyoung Tae Youm, Ryan K. Totten, Joseph T Hupp, Sonbinh T. Nguyen

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Box-like tetrakis(metalloporphyrin) supramolecular assemblies possessing Zn and Al metal sites can catalyze the methanolysis of phosphate triesters with a high rate enhancement, up to 430 times faster than the uncatalyzed reaction. Mechanistic studies suggest that the observed rate enhancement can be attributed to a high local concentration of methoxide ion that operates in concert with a solvophobically driven encapsulation of substrates by the porphyrinic assembly.

Original languageEnglish
Pages (from-to)1938-1944
Number of pages7
JournalChemical Science
Volume3
Issue number6
DOIs
Publication statusPublished - Jun 2012

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Porphyrins
Encapsulation
Phosphates
Metalloporphyrins
Metals
Ions
Substrates

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Catalytically active supramolecular porphyrin boxes : Acceleration of the methanolysis of phosphate triesters via a combination of increased local nucleophilicity and reactant encapsulation. / Kang, Byungman; Kurutz, Josh W.; Youm, Kyoung Tae; Totten, Ryan K.; Hupp, Joseph T; Nguyen, Sonbinh T.

In: Chemical Science, Vol. 3, No. 6, 06.2012, p. 1938-1944.

Research output: Contribution to journalArticle

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