Issue 6, 2012
From the journal:

Chemical Science

Catalytically active supramolecular porphyrin boxes: acceleration of the methanolysis of phosphate triesters via a combination of increased local nucleophilicity and reactant encapsulation†

Byungman Kang,a   Josh W. Kurutz,a   Kyoung-Tae Youm,‡a   Ryan K. Totten,a   Joseph T. Hupp*a  and  SonBinh T. Nguyen*a  

* Corresponding authors

a Department of Chemistry and International Institute for Nanotechnology, Northwestern University, 2145 Sheridan Road, Evanston, IL, USA
E-mail: j-hupp@northwestern.edu, stn@northwestern.edu
Fax: +1 847 491-7713
Tel: +1 847-467-3347

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.

Graphical abstract: Catalytically active supramolecular porphyrin boxes: acceleration of the methanolysis of phosphate triesters via a combination of increased local nucleophilicity and reactant encapsulation

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Article information

DOI
https://doi.org/10.1039/C2SC00950A
Article type
Edge Article
Submitted
21 Nov 2011
Accepted
25 Jan 2012
First published
26 Jan 2012

Chem. Sci., 2012,3, 1938-1944

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Catalytically active supramolecular porphyrin boxes: acceleration of the methanolysis of phosphate triesters via a combination of increased local nucleophilicity and reactant encapsulation

B. Kang, J. W. Kurutz, K. Youm, R. K. Totten, J. T. Hupp and S. T. Nguyen, Chem. Sci., 2012, 3, 1938 DOI: 10.1039/C2SC00950A

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