Hybrid organic-inorganic catalytic mesoporous materials with proton sponges as building blocks

dc.contributor.affiliationInstituto Universitario Mixto de Tecnología Química
dc.contributor.authorGianotti, Enricaes_ES
dc.contributor.authorDíaz, Urbano
dc.contributor.authorColuccia, Salvatorees_ES
dc.contributor.authorCorma Canós, Avelino
dc.contributor.funderEuropean Commission
dc.date.accessioned2016-06-20T10:13:03Z
dc.date.available2016-06-20T10:13:03Z
dc.date.issued2011
dc.description.abstract[EN] Non-ordered organic-inorganic mesoporous hybrid materials with basic sites have been synthesized following a fluoride-catalysed sol-gel process at neutral pH and low temperatures that avoids the use of structural directing agents (SDAs). Proton sponges have been used as the organic builder of the hybrids, while the inorganic part corresponds to silica tetrahedra. The proton sponges are diamines that exhibit very high basicity and, after functionalization, have been introduced as part of the walls of the mesoporous silica by one-pot synthesis. Several hybrids with different organic loadings have been synthesized and characterized by gas adsorption, thermogravimetric and elemental analysis, solid state MAS-NMR and FTIR spectroscopy. These hybrids show high activity as base catalysts and can be recycled.en_EN
dc.description.accrualMethodSes_ES
dc.description.bibliographicCitationGianotti, E.; Díaz Morales, UM.; Coluccia, S.; Corma Canós, A. (2011). Hybrid organic-inorganic catalytic mesoporous materials with proton sponges as building blocks. Physical Chemistry Chemical Physics. 13(24):11702-11709. https://doi.org/10.1039/c1cp20588aes_ES
dc.description.issue24es_ES
dc.description.referencesHoffmann, F., Cornelius, M., Morell, J., & Fröba, M. (2006). Silica-Based Mesoporous Organic–Inorganic Hybrid Materials. Angewandte Chemie International Edition, 45(20), 3216-3251. doi:10.1002/anie.200503075es_ES
dc.description.referencesSanchez, C., Rozes, L., Ribot, F., Laberty-Robert, C., Grosso, D., Sassoye, C., … Nicole, L. (2010). «Chimie douce»: A land of opportunities for the designed construction of functional inorganic and hybrid organic-inorganic nanomaterials. Comptes Rendus Chimie, 13(1-2), 3-39. doi:10.1016/j.crci.2009.06.001es_ES
dc.description.referencesSanchez, C., Julián, B., Belleville, P., & Popall, M. (2005). Applications of hybrid organic–inorganic nanocomposites. Journal of Materials Chemistry, 15(35-36), 3559. doi:10.1039/b509097kes_ES
dc.description.referencesWight, A. P., & Davis, M. E. (2002). Design and Preparation of Organic−Inorganic Hybrid Catalysts. Chemical Reviews, 102(10), 3589-3614. doi:10.1021/cr010334mes_ES
dc.description.referencesVallé, K., Belleville, P., Pereira, F., & Sanchez, C. (2006). Hierarchically structured transparent hybrid membranes by in situ growth of mesostructured organosilica in host polymer. Nature Materials, 5(2), 107-111. doi:10.1038/nmat1570es_ES
dc.description.referencesKapoor, M. P., & Inagaki, S. (2006). Highly Ordered Mesoporous Organosilica Hybrid Materials. Bulletin of the Chemical Society of Japan, 79(10), 1463-1475. doi:10.1246/bcsj.79.1463es_ES
dc.description.referencesDamrau, U., & Marsmann, H. C. (1994). The hydrolysis of oligomer intermediates in the sol-gel process. Journal of Non-Crystalline Solids, 168(1-2), 42-48. doi:10.1016/0022-3093(94)90118-xes_ES
dc.description.referencesRaman, N. K., Ward, T. L., Brinker, C. J., Sehgal, R., Smith, D. M., Duan, Z., … Headley, T. J. (1993). Catalyst dispersion on supported ultramicroporous inorganic membranes using derivatized silylation agents. Applied Catalysis A: General, 96(1), 65-82. doi:10.1016/0926-860x(93)80007-des_ES
dc.description.referencesBoury, B., & Corriu, R. J. P. (2002). Auto-organisation of hybrid organic–inorganic materials prepared by sol–gel chemistry. Chemical Communications, (8), 795-802. doi:10.1039/b109040mes_ES
dc.description.referencesMehdi, A., Reye, C., & Corriu, R. (2011). From molecular chemistry to hybrid nanomaterials. Design and functionalization. Chem. Soc. Rev., 40(2), 563-574. doi:10.1039/b920516kes_ES
dc.description.referencesPope, E. J. A., & Mackenzie, J. D. (1986). Sol-gel processing of silica. Journal of Non-Crystalline Solids, 87(1-2), 185-198. doi:10.1016/s0022-3093(86)80078-3es_ES
dc.description.referencesWinter, R., Chan, J.-B., Frattini, R., & Jonas, J. (1988). The effect of fluoride on the sol-gel process. Journal of Non-Crystalline Solids, 105(3), 214-222. doi:10.1016/0022-3093(88)90310-9es_ES
dc.description.referencesReale, E., Leyva, A., Corma, A., Martínez, C., García, H., & Rey, F. (2005). A fluoride-catalyzed sol–gel route to catalytically active non-ordered mesoporous silica materials in the absence of surfactants. Journal of Materials Chemistry, 15(17), 1742. doi:10.1039/b415066jes_ES
dc.description.referencesDíaz, U., García, T., Velty, A., & Corma, A. (2009). Hybrid organic–inorganic catalytic porous materials synthesized at neutral pH in absence of structural directing agents. Journal of Materials Chemistry, 19(33), 5970. doi:10.1039/b906821jes_ES
dc.description.referencesAlder, R. W. (1989). Strain effects on amine basicities. Chemical Reviews, 89(5), 1215-1223. doi:10.1021/cr00095a015es_ES
dc.description.referencesLlamas-Saiz, A. L., Foces-Foces, C., & Elguero, J. (1994). Proton sponges. Journal of Molecular Structure, 328, 297-323. doi:10.1016/0022-2860(94)08367-3es_ES
dc.description.referencesHoward, S. T. (2000). Relationship between Basicity, Strain, and Intramolecular Hydrogen-Bond Energy in Proton Sponges. Journal of the American Chemical Society, 122(34), 8238-8244. doi:10.1021/ja0010094es_ES
dc.description.referencesRodriguez, I., Sastre, G., Corma, A., & Iborra, S. (1999). Catalytic Activity of Proton Sponge: Application to Knoevenagel Condensation Reactions. Journal of Catalysis, 183(1), 14-23. doi:10.1006/jcat.1998.2380es_ES
dc.description.referencesCLIMENT, M., CORMA, A., DOMINGUEZ, I., IBORRA, S., SABATER, M., & SASTRE, G. (2007). Gem-diamines as highly active organocatalysts for carbon–carbon bond formation. Journal of Catalysis, 246(1), 136-146. doi:10.1016/j.jcat.2006.11.029es_ES
dc.description.referencesSing, K. S. W. (1985). Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Recommendations 1984). Pure and Applied Chemistry, 57(4), 603-619. doi:10.1351/pac198557040603es_ES
dc.description.referencesBarrett, E. P., Joyner, L. G., & Halenda, P. P. (1951). The Determination of Pore Volume and Area Distributions in Porous Substances. I. Computations from Nitrogen Isotherms. Journal of the American Chemical Society, 73(1), 373-380. doi:10.1021/ja01145a126es_ES
dc.description.referencesWoźniak, K. (1996). Proton sponges: solid-state NMR spectra of ionic complexes of 1,8-bis(dimethylamino)naphthalene. Journal of Molecular Structure, 374(1-3), 317-326. doi:10.1016/0022-2860(95)08947-0es_ES
dc.description.referencesPozharskii, A. F. (1998). Naphthalene «proton sponges». Russian Chemical Reviews, 67(1), 1-24. doi:10.1070/rc1998v067n01abeh000377es_ES
dc.description.referencesSeo, Y.-K., Park, S.-B., & Ho Park, D. (2006). Mesoporous hybrid organosilica containing urethane moieties. Journal of Solid State Chemistry, 179(4), 1285-1288. doi:10.1016/j.jssc.2006.01.021es_ES
dc.description.referencesKawahara, K., Hagiwara, Y., Shimojima, A., & Kuroda, K. (2008). Stepwise silylation of double-four-ring (D4R) silicate into a novel spherical siloxane with a defined architecture. Journal of Materials Chemistry, 18(27), 3193. doi:10.1039/b807533fes_ES
dc.description.referencesVan Meervelt, L., Platteborze, K., & Zeegers-Huyskens, T. (1994). X-Ray and Fourier-transform infrared studies of 1,8-bis(dimethylaminomethyl)naphthalene. Comparison with 1,8-bis(dimethylamino)naphthalene. Journal of the Chemical Society, Perkin Transactions 2, (5), 1087. doi:10.1039/p29940001087es_ES
dc.description.referencesBrzeziński, B., Schroeder, G., Grech, E., Malarski, Z., & Sobczyk, L. (1992). Basicity, IR spectra and protonation of some proton sponges in acetonitrile. Journal of Molecular Structure, 274, 75-82. doi:10.1016/0022-2860(92)80147-aes_ES
dc.description.referencesRodriguez, I., Iborra, S., Rey, F., & Corma, A. (2000). Heterogeneized Brönsted base catalysts for fine chemicals production: grafted quaternary organic ammonium hydroxides as catalyst for the production of chromenes and coumarins. Applied Catalysis A: General, 194-195, 241-252. doi:10.1016/s0926-860x(99)00371-3es_ES
dc.description.referencesCLIMENT, M. (2004). Increasing the basicity and catalytic activity of hydrotalcites by different synthesis procedures. Journal of Catalysis, 225(2), 316-326. doi:10.1016/j.jcat.2004.04.027es_ES
dc.description.referencesProut, F. S., Beaucaire, V. D., Dyrkacz, G. R., Koppes, W. M., Kuznicki, R. E., Marlewski, T. A., … Puda, J. M. (1973). Konevenagel Reaction. Kinetic study of the reaction of (+)-3-methyl-cyclohexanone with malononitrile. The Journal of Organic Chemistry, 38(8), 1512-1517. doi:10.1021/jo00948a015es_ES
dc.description.referencesGuyot, J., & Kergomard, A. (1983). Cinétique et mécanisme de la réaction de knoevenagel dans le benzène—1. Tetrahedron, 39(7), 1161-1166. doi:10.1016/s0040-4020(01)91879-4es_ES
dc.description.referencesMotokura, K., Tanaka, S., Tada, M., & Iwasawa, Y. (2009). Bifunctional Heterogeneous Catalysis of Silica-Alumina-Supported Tertiary Amines with Controlled Acid-Base Interactions for Efficient 1,4-Addition Reactions. Chemistry - A European Journal, 15(41), 10871-10879. doi:10.1002/chem.200901380es_ES
dc.description.sponsorshipThe authors thank financial support by Consolider-Ingenio (MULTICAT project) from Spanish Government. EG thanks Marie Curie Fellowship (FP7-PEOPLE-2009-IEF) for financial support.en_EN
dc.description.upvformatpfin11709es_ES
dc.description.upvformatpinicio11702es_ES
dc.description.volume13es_ES
dc.identifier.doi10.1039/c1cp20588a
dc.identifier.issn1463-9076
dc.identifier.urihttps://riunet.upv.es/handle/10251/66163
dc.languageIngléses_ES
dc.publisherRoyal Society of Chemistryes_ES
dc.relation.ispartofPhysical Chemistry Chemical Physicses_ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/FP7/252367/EU/Decomposition of Structured Tensors, Algorithms and Characterization./
dc.relation.publisherversionhttp://dx.doi.org/10.1039/c1cp20588aes_ES
dc.relation.references10.1002/anie.200503075es_ES
dc.relation.references10.1016/j.crci.2009.06.001es_ES
dc.relation.references10.1039/b509097kes_ES
dc.relation.references10.1021/cr010334mes_ES
dc.relation.references10.1038/nmat1570es_ES
dc.relation.references10.1246/bcsj.79.1463es_ES
dc.relation.references10.1016/0022-3093(94)90118-Xes_ES
dc.relation.references10.1016/0926-860X(93)80007-Des_ES
dc.relation.references10.1039/b109040mes_ES
dc.relation.references10.1039/B920516Kes_ES
dc.relation.references10.1016/S0022-3093(86)80078-3es_ES
dc.relation.references10.1016/0022-3093(88)90310-9es_ES
dc.relation.references10.1039/b415066jes_ES
dc.relation.references10.1039/b906821jes_ES
dc.relation.references10.1021/cr00095a015es_ES
dc.relation.references10.1016/0022-2860(94)08367-3es_ES
dc.relation.references10.1021/ja0010094es_ES
dc.relation.references10.1006/jcat.1998.2380es_ES
dc.relation.references10.1016/j.jcat.2006.11.029es_ES
dc.relation.references10.1351/pac198557040603es_ES
dc.relation.references10.1021/ja01145a126es_ES
dc.relation.references10.1016/0022-2860(95)08947-0es_ES
dc.relation.references10.1070/RC1998v067n01ABEH000377es_ES
dc.relation.references10.1016/j.jssc.2006.01.021es_ES
dc.relation.references10.1039/b807533fes_ES
dc.relation.references10.1039/p29940001087es_ES
dc.relation.references10.1016/0022-2860(92)80147-Aes_ES
dc.relation.references10.1016/S0926-860X(99)00371-3es_ES
dc.relation.references10.1016/j.jcat.2004.04.027es_ES
dc.relation.references10.1021/jo00948a015es_ES
dc.relation.references10.1016/S0040-4020(01)91879-4es_ES
dc.relation.references10.1002/chem.200901380es_ES
dc.relation.senia209014es_ES
dc.rightsReserva de todos los derechoses_ES
dc.rights.accessRightsAbiertoes_ES
dc.subject.classificationQUIMICA ORGANICAes_ES
dc.titleHybrid organic-inorganic catalytic mesoporous materials with proton sponges as building blockses_ES
dc.typeArtículoes_ES
dc.type.versioninfo:eu-repo/semantics/publishedVersiones_ES
dspace.entity.typePublication
person.identifier180432
person.identifier180535
person.identifier.orcid0000-0003-1472-8724
person.identifier.orcid0000-0002-2232-3527
relation.isAuthorOfPublication5dd76f1e-de72-413d-b900-5ab52e5bb6b1
relation.isAuthorOfPublication6613f49c-4788-4ac7-b485-26926d2a99ca
relation.isAuthorOfPublication.latestForDiscovery5dd76f1e-de72-413d-b900-5ab52e5bb6b1
relation.isOrgUnitOfPublicationb97c2806-5147-442a-a1a8-a2c75cc2a941
relation.isOrgUnitOfPublication.latestForDiscoveryb97c2806-5147-442a-a1a8-a2c75cc2a941
upv.uuid369b1c49-f293-4d14-a579-4a18320687b1es_ES

Archivos

Bloque original

Mostrando 1 - 2 de 2
Cargando...
Miniatura
Nombre:
Gianotti, E. et al. - Organic-inorganic mesoporous....pdf
Tamaño:
695.97 KB
Formato:
Adobe Portable Document Format
Descripción:
Versión del Autor.
Cargando...
Miniatura
Nombre:
Corma;DÍAZ;GIANOTTI - Hybrid organic-inorganic catalytic mesoporous materials with proton sponges....pdf
Tamaño:
978.34 KB
Formato:
Adobe Portable Document Format
Descripción:
Versión editorial