Turning on catalysis: Incorporation of a hydrogen-bond-donating squaramide moiety into a Zr metal-organic framework

C. Michael McGuirk; Michael J. Katz; Charlotte L. Stern; Amy A. Sarjeant; Joseph T. Hupp; Omar K. Farha; Chad A. Mirkin

doi:10.1021/ja511403t

Turning on catalysis: Incorporation of a hydrogen-bond-donating squaramide moiety into a Zr metal-organic framework

C. Michael McGuirk, Michael J. Katz, Charlotte L. Stern, Amy A. Sarjeant, Joseph T. Hupp, Omar K. Farha, Chad A. Mirkin

Northwestern University

Research output: Contribution to journal › Article

125 Citations (Scopus)

Abstract

Herein, we demonstrate that the incorporation of an acidic hydrogen-bond-donating squaramide moiety into a porous UiO-67 metal-organic framework (MOF) derivative leads to dramatic acceleration of the biorelevant Friedel-Crafts reaction between indole and β-nitrostyrene. In comparison, it is shown that free squaramide derivatives, not incorporated into MOF architectures, have no catalytic activity. Additionally, using the UiO-67 template, we were able to perform a direct comparison of catalytic activity with that of the less acidic urea-based analogue. This is the first demonstration of the functionalization of a heterogeneous framework with an acidic squaramide derivative.

Original language	English
Pages (from-to)	919-925
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	137
Issue number	2
DOIs	https://doi.org/10.1021/ja511403t
Publication status	Published - Jan 21 2015

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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McGuirk, C. M., Katz, M. J., Stern, C. L., Sarjeant, A. A., Hupp, J. T., Farha, O. K., & Mirkin, C. A. (2015). Turning on catalysis: Incorporation of a hydrogen-bond-donating squaramide moiety into a Zr metal-organic framework. Journal of the American Chemical Society, 137(2), 919-925. https://doi.org/10.1021/ja511403t

Turning on catalysis : Incorporation of a hydrogen-bond-donating squaramide moiety into a Zr metal-organic framework. / McGuirk, C. Michael; Katz, Michael J.; Stern, Charlotte L.; Sarjeant, Amy A.; Hupp, Joseph T.; Farha, Omar K.; Mirkin, Chad A.

In: Journal of the American Chemical Society, Vol. 137, No. 2, 21.01.2015, p. 919-925.

Research output: Contribution to journal › Article

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