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

*Corresponding author for this work

Research output: Contribution to journalArticle

126 Scopus citations

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 (US)
Pages (from-to)919-925
Number of pages7
JournalJournal of the American Chemical Society
Volume137
Issue number2
DOIs
StatePublished - Jan 21 2015

ASJC Scopus subject areas

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

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