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Facile synthesis of cooperative acid-base catalysts by clicking cysteine and cysteamine on an ethylene-bridged periodic mesoporous organosilica

Author
Organization
Project
FWO grant G006813N
Project
UGent GOA grant 01G00710
Project
Long Term Structural Methusalem Funding by the Flemish Government
Abstract
A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid-base catalysts. A straightforward, single-step procedure was devised to immobilize cysteine and cysteamine on the support material by means of a photoinitiated thiol-ene click reaction. Likewise, PMO materials capped with hexamethyldisilazane (HMDS) were used to support both compounds. This resulted in different materials in which the amine site was promoted by carboxylic acid groups, surface silanol groups, or both. The catalysts were tested in the aldol reaction of 4-nitrobenzaldehyde and acetone. It was found that silanol groups have a stronger promoting effect on the amine than the carboxylic acid group. The highest turnover frequency (TOF) was obtained for an amine-functionalized material that contained only silanol promoting sites. The loading of the active sites also had a significant effect on the activity of the catalysts, which was rationalized on the basis of a computational study.
Keywords
Click chemistry, Heterogeneous catalysis, Amino acids, Aldol reactions, Mesoporous materials

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Citation

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MLA
Ouwehand, Judith et al. “Facile Synthesis of Cooperative Acid-base Catalysts by Clicking Cysteine and Cysteamine on an Ethylene-bridged Periodic Mesoporous Organosilica.” EUROPEAN JOURNAL OF INORGANIC CHEMISTRY 13-14 (2016): 2144–2151. Print.
APA
Ouwehand, J., Lauwaert, J., Esquivel Merino, M. D., Hendrickx, K., Van Speybroeck, V., Thybaut, J., & Van Der Voort, P. (2016). Facile synthesis of cooperative acid-base catalysts by clicking cysteine and cysteamine on an ethylene-bridged periodic mesoporous organosilica. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, (13-14), 2144–2151.
Chicago author-date
Ouwehand, Judith, Jeroen Lauwaert, Maria Dolores Esquivel Merino, Kevin Hendrickx, Veronique Van Speybroeck, Joris Thybaut, and Pascal Van Der Voort. 2016. “Facile Synthesis of Cooperative Acid-base Catalysts by Clicking Cysteine and Cysteamine on an Ethylene-bridged Periodic Mesoporous Organosilica.” European Journal of Inorganic Chemistry (13-14): 2144–2151.
Chicago author-date (all authors)
Ouwehand, Judith, Jeroen Lauwaert, Maria Dolores Esquivel Merino, Kevin Hendrickx, Veronique Van Speybroeck, Joris Thybaut, and Pascal Van Der Voort. 2016. “Facile Synthesis of Cooperative Acid-base Catalysts by Clicking Cysteine and Cysteamine on an Ethylene-bridged Periodic Mesoporous Organosilica.” European Journal of Inorganic Chemistry (13-14): 2144–2151.
Vancouver
1.
Ouwehand J, Lauwaert J, Esquivel Merino MD, Hendrickx K, Van Speybroeck V, Thybaut J, et al. Facile synthesis of cooperative acid-base catalysts by clicking cysteine and cysteamine on an ethylene-bridged periodic mesoporous organosilica. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY. 2016;(13-14):2144–51.
IEEE
[1]
J. Ouwehand et al., “Facile synthesis of cooperative acid-base catalysts by clicking cysteine and cysteamine on an ethylene-bridged periodic mesoporous organosilica,” EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, no. 13–14, pp. 2144–2151, 2016.
@article{7247855,
  abstract     = {A periodic mesoporous organosilica (PMO) that contains ethylene bridges was functionalized to obtain a series of cooperative acid-base catalysts. A straightforward, single-step procedure was devised to immobilize cysteine and cysteamine on the support material by means of a photoinitiated thiol-ene click reaction. Likewise, PMO materials capped with hexamethyldisilazane (HMDS) were used to support both compounds. This resulted in different materials in which the amine site was promoted by carboxylic acid groups, surface silanol groups, or both. The catalysts were tested in the aldol reaction of 4-nitrobenzaldehyde and acetone. It was found that silanol groups have a stronger promoting effect on the amine than the carboxylic acid group. The highest turnover frequency (TOF) was obtained for an amine-functionalized material that contained only silanol promoting sites. The loading of the active sites also had a significant effect on the activity of the catalysts, which was rationalized on the basis of a computational study.},
  author       = {Ouwehand, Judith and Lauwaert, Jeroen and Esquivel Merino, Maria Dolores and Hendrickx, Kevin and Van Speybroeck, Veronique and Thybaut, Joris and Van Der Voort, Pascal},
  issn         = {1434-1948},
  journal      = {EUROPEAN JOURNAL OF INORGANIC CHEMISTRY},
  keywords     = {Click chemistry,Heterogeneous catalysis,Amino acids,Aldol reactions,Mesoporous materials},
  language     = {eng},
  number       = {13-14},
  pages        = {2144--2151},
  title        = {Facile synthesis of cooperative acid-base catalysts by clicking cysteine and cysteamine on an ethylene-bridged periodic mesoporous organosilica},
  url          = {http://dx.doi.org/10.1002/ejic.201501179},
  year         = {2016},
}

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