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

119 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

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ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Cite this

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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10.1021/ja511403t