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Formation and functionalization of surface Diels–Alder adducts on ethenylene-bridged periodic mesoporous organosilica

Dolores Esquivel, Els De Canck UGent, César Jiménez-Sanchidrián, Pascal Van Der Voort UGent and Francisco Romero-Salguero (2011) JOURNAL OF MATERIALS CHEMISTRY. 21(29). p.10990-10998
abstract
The Diels-Alder cycloaddition of two common dienes (cyclopentadiene and anthracene) to the double carbon-carbon bonds of an ethenylene-bridged periodic mesoporous organosilica was studied and compared to that of benzocyclobutene. The resulting materials were characterized by several techniques such as X-ray and thermal analyses, DRIFT, (13)C and (29)Si MAS NMR and porosimetry. They showed that the mesopores were decorated with the Diels-Alder adducts with negligible structural degradation and with the concomitant reduction of the surface area and pore size. The formation of surface adducts was even successful with a relatively hindered diene such as anthracene. The surface Diels-Alder adducts were stable and susceptible to further functionalization. Thus, after being sulfonated, the resulting solids were used as acid catalysts in the esterification of acetic acid with ethanol, a process in which they proved to be very active. In fact, each acid site of these hybrid materials was up to three times more active than a similar site in Amberlyst-15, a commercial acid resin.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
ORGANIC GROUPS, ALLYLORGANOSILANE PRECURSORS, SILICA, HYBRIDS, FRAMEWORKS, CATALYST
journal title
JOURNAL OF MATERIALS CHEMISTRY
J. Mater. Chem.
volume
21
issue
29
pages
10990 - 10998
Web of Science type
Article
Web of Science id
000292978600060
JCR category
MATERIALS SCIENCE, MULTIDISCIPLINARY
JCR impact factor
5.968 (2011)
JCR rank
17/229 (2011)
JCR quartile
1 (2011)
ISSN
0959-9428
DOI
10.1039/c1jm11315a
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1859583
handle
http://hdl.handle.net/1854/LU-1859583
date created
2011-07-14 16:39:17
date last changed
2018-01-29 12:12:59
@article{1859583,
  abstract     = {The Diels-Alder cycloaddition of two common dienes (cyclopentadiene and anthracene) to the double carbon-carbon bonds of an ethenylene-bridged periodic mesoporous organosilica was studied and compared to that of benzocyclobutene. The resulting materials were characterized by several techniques such as X-ray and thermal analyses, DRIFT, (13)C and (29)Si MAS NMR and porosimetry. They showed that the mesopores were decorated with the Diels-Alder adducts with negligible structural degradation and with the concomitant reduction of the surface area and pore size. The formation of surface adducts was even successful with a relatively hindered diene such as anthracene. The surface Diels-Alder adducts were stable and susceptible to further functionalization. Thus, after being sulfonated, the resulting solids were used as acid catalysts in the esterification of acetic acid with ethanol, a process in which they proved to be very active. In fact, each acid site of these hybrid materials was up to three times more active than a similar site in Amberlyst-15, a commercial acid resin.},
  author       = {Esquivel, Dolores and De Canck, Els and Jim{\'e}nez-Sanchidri{\'a}n, C{\'e}sar and Van Der Voort, Pascal and Romero-Salguero, Francisco},
  issn         = {0959-9428},
  journal      = {JOURNAL OF MATERIALS CHEMISTRY},
  keyword      = {ORGANIC GROUPS,ALLYLORGANOSILANE PRECURSORS,SILICA,HYBRIDS,FRAMEWORKS,CATALYST},
  language     = {eng},
  number       = {29},
  pages        = {10990--10998},
  title        = {Formation and functionalization of surface Diels--Alder adducts on ethenylene-bridged periodic mesoporous organosilica},
  url          = {http://dx.doi.org/10.1039/c1jm11315a},
  volume       = {21},
  year         = {2011},
}

Chicago
Esquivel, Dolores, Els De Canck, César Jiménez-Sanchidrián, Pascal Van Der Voort, and Francisco Romero-Salguero. 2011. “Formation and Functionalization of Surface Diels–Alder Adducts on Ethenylene-bridged Periodic Mesoporous Organosilica.” Journal of Materials Chemistry 21 (29): 10990–10998.
APA
Esquivel, D., De Canck, E., Jiménez-Sanchidrián, C., Van Der Voort, P., & Romero-Salguero, F. (2011). Formation and functionalization of surface Diels–Alder adducts on ethenylene-bridged periodic mesoporous organosilica. JOURNAL OF MATERIALS CHEMISTRY, 21(29), 10990–10998.
Vancouver
1.
Esquivel D, De Canck E, Jiménez-Sanchidrián C, Van Der Voort P, Romero-Salguero F. Formation and functionalization of surface Diels–Alder adducts on ethenylene-bridged periodic mesoporous organosilica. JOURNAL OF MATERIALS CHEMISTRY. 2011;21(29):10990–8.
MLA
Esquivel, Dolores, Els De Canck, César Jiménez-Sanchidrián, et al. “Formation and Functionalization of Surface Diels–Alder Adducts on Ethenylene-bridged Periodic Mesoporous Organosilica.” JOURNAL OF MATERIALS CHEMISTRY 21.29 (2011): 10990–10998. Print.