Self-assembly of a silylated steroid-based organogelator and its use as template for the in situ sol-gel polymerization of tetraethyl orthosilicate

In this paper we report the synthesis of a new steroid-based low-molecular weight organogelator, the analysis of the self-assembled fibrilar network (SAFIN) and its use as template for the preparation of SiO2 nanotubes. This novel steroidal organogelator has a unique structure among the well known f...

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Autor principal: Edelsztein, V.C
Otros Autores: Burton, G., Di Chenna, P.H
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2010
Acceso en línea:Registro en Scopus
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024 7 |2 cas  |a silicate, 12627-13-3; silicon dioxide, 10279-57-9, 14464-46-1, 14808-60-7, 15468-32-3, 60676-86-0, 7631-86-9 
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100 1 |a Edelsztein, V.C. 
245 1 0 |a Self-assembly of a silylated steroid-based organogelator and its use as template for the in situ sol-gel polymerization of tetraethyl orthosilicate 
260 |c 2010 
270 1 0 |m Di Chenna, P.H.; Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon 2, C1428EGA Buenos Aires, Argentina; email: dichenna@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Dastidar, P., (2008) Chem. Soc. Rev., 37, p. 2699 
504 |a Llusar, M., Sanchez, C., (2008) Chem. Mater., 20, p. 782 
504 |a Fujita, N., Shinkai, S., (2006) Molecular Gels: Materials with Self-assembled Fibrillar Networks, pp. 553-575. , Weiss R.G., and Terech P. (Eds), Springer, The Netherlands Chapter 15 
504 |a Sugiyasu, K., Fujita, N., Shinkai, S., (2004) Angew. Chem., Int. Ed., 43, p. 1229 
504 |a Kawano, S., Fujita, N., Shinkai, S., (2003) Chem. Commun., p. 1352 
504 |a Huang, X., Weiss, R.G., (2007) Tetrahedron, 63, p. 7375 
504 |a Huang, P., Terech, P., Raghavan, S.R., Weiss, R.G., (2005) J. Am. Chem. Soc., 127, p. 4336 
504 |a Jiang, Q., Wang, Y., Weng, J., Liu, L., Zhou, Z., Zhang, Q., Chen, H., Yang, W., (2009) Curr. Nanosci., 5, p. 245 
504 |a Durán, F.J., Ghini, A.A., Coirini, H., Burton, G., (2006) Tetrahedron, 62, p. 4762 
504 |a Nicoletti, D., Ghini, A.A., Brachet-Cota, A.L., Burton, G., (1995) J. Chem. Soc., Perkin Trans. 1, p. 1089 
504 |a De Armas, P., Concepción, J.L., Francisco, C.G., Hernandez, R., Salazar, J.A., Suárez, E., (1989) J. Chem. Soc., Perkin Trans. 1, p. 405 
504 |a Hirst, A.R., Coates, I.A., Boucheteau, T.R., Miravet, J.F., Escuder, B., Castelletto, V., Hamley, I.W., Smith, D.K., (2008) J. Am. Chem. Soc., 130, p. 9113 
504 |a Xue, M., Gao, D., Liu, K., Peng, J., Fang, Y., (2009) Tetrahedron, 65, p. 3369 
504 |a Yoshikawa, I., Yanagi, S., Yamaji, Y., Araki, K., (2007) Tetrahedron, 63, p. 7474 
504 |a Joselevich, M., Ghini, A.A., Burton, G., (2003) Org. Biomol. Chem., p. 939 
520 3 |a In this paper we report the synthesis of a new steroid-based low-molecular weight organogelator, the analysis of the self-assembled fibrilar network (SAFIN) and its use as template for the preparation of SiO2 nanotubes. This novel steroidal organogelator has a unique structure among the well known family of steroid-based organogelators, the most important characteristic of this molecule is the presence of a silyl ether group at C-3 together with a 6β,19-oxo bridge. It was capable to gelate hydrocarbons and tetraethyl orthosilicate at very low concentrations (<1 wt %). An insight into the aggregation mechanism is provided revealing that complementary interaction between an α-oriented hydrogen bond donor and a β-oriented acceptor on the steroid skeleton is the driving force for the primary 1D self-assembly. The SAFIN was successfully used as template to grow silica nanotubes (external diameter: 40-60 nm, internal diameter: 7 nm and several micrometers length) through a catalyst-free in situ co-assembly polymerization process. Hydrogen bond or electrostatic interactions between the anionic silicate intermediate species and the SAFIN are proposed to be the driving force for templating. © 2010 Elsevier Ltd. All rights reserved.  |l eng 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT2006-765 
536 |a Detalles de la financiación: Universidad de Buenos Aires, X-614 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: This work was supported by grants from Universidad de Buenos Aires (X-614), CONICET (Argentina), and Agencia Nacional de Promoción Científica y Tecnológica (PICT2006-765). 
593 |a Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon 2, C1428EGA Buenos Aires, Argentina 
690 1 0 |a ORGANOGEL 
690 1 0 |a SILICA NANOTUBES 
690 1 0 |a STEROID 
690 1 0 |a TEMPLATE 
690 1 0 |a NANOTUBE 
690 1 0 |a SILANE DERIVATIVE 
690 1 0 |a SILICATE 
690 1 0 |a SILICON DIOXIDE 
690 1 0 |a STEROID 
690 1 0 |a TETRAETHOXYSILANE 
690 1 0 |a ARTICLE 
690 1 0 |a CHEMICAL ANALYSIS 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a HYDROGEN BOND 
690 1 0 |a POLYMERIZATION 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a SILYLATION 
690 1 0 |a SYNTHESIS 
700 1 |a Burton, G. 
700 1 |a Di Chenna, P.H. 
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