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

Research output: Contribution to journalArticle

105 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 languageEnglish
Pages (from-to)919-925
Number of pages7
JournalJournal of the American Chemical Society
Volume137
Issue number2
DOIs
Publication statusPublished - Jan 21 2015

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Catalysis
Hydrogen
Hydrogen bonds
Metals
Derivatives
Catalyst activity
Friedel-Crafts reaction
Urea
Demonstrations
squaramide

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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 journalArticle

McGuirk, C. Michael ; Katz, Michael J. ; Stern, Charlotte L. ; Sarjeant, Amy A. ; Hupp, Joseph T ; Farha, Omar K. ; Mirkin, Chad A. / Turning on catalysis : Incorporation of a hydrogen-bond-donating squaramide moiety into a Zr metal-organic framework. In: Journal of the American Chemical Society. 2015 ; Vol. 137, No. 2. pp. 919-925.
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