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 | |
| Publication status | Published - Jan 21 2015 |
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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 journal › Article
}
TY - JOUR
T1 - Turning on catalysis
T2 - Incorporation of a hydrogen-bond-donating squaramide moiety into a Zr metal-organic framework
AU - McGuirk, C. Michael
AU - Katz, Michael J.
AU - Stern, Charlotte L.
AU - Sarjeant, Amy A.
AU - Hupp, Joseph T
AU - Farha, Omar K.
AU - Mirkin, Chad A.
PY - 2015/1/21
Y1 - 2015/1/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84922854786&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84922854786&partnerID=8YFLogxK
U2 - 10.1021/ja511403t
DO - 10.1021/ja511403t
M3 - Article
AN - SCOPUS:84922854786
VL - 137
SP - 919
EP - 925
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 2
ER -