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

(2011) JOURNAL OF MATERIALS CHEMISTRY. 21(29). p.10990-10998
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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.
Keywords
ORGANIC GROUPS, ALLYLORGANOSILANE PRECURSORS, SILICA, HYBRIDS, FRAMEWORKS, CATALYST

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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.
@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},
}

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