Navegar

Colección

Datos Estadísticas

Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The Cu(I)-catalyzed, microwave-assisted click polymerization of bio-based α-azide-ω-alkyne monomers afforded, with high regioselectivity, stereoregular poly(amide-triazole)s. The monomers were prepared starting from d-glucono-1,5-lactone as a renewable resource. The synthetic route involves the selective protection of this sugar lactone with formaldehyde to give a gluconic acid derivative, which was subjected to amidation of the carboxylic acid function with alkynylamines (2-propynyl, 3-butynyl, and 4-pentynylamines) and substitution of the primary hydroxyl group by azide. The regioselective click polymerization of these AB-type alkyne/azide monomers led to a series of linear biosourced poly(amide-triazole)s containing mostly (>95%) 1,4-disubstituted triazole linkages. In contrast, the thermal, metal-free click polymerization led to random distribution of 1,4- and 1,5-disubstituted triazoles in the polymer backbone. The length of the methylene chain linked to the amide of the monomer and the cycloaddition regioselectivity strongly affected the properties of the materials, mainly the Tg values, which were unexpectedly high. © 2014 Elsevier Ltd.

Registro:

Documento: Artículo
Título:Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers
Autor:Fidalgo, D.M.; Kolender, A.A.; Varela, O.
Filiación:CIHIDECAR-CONICET-UBA, Dpto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
Palabras clave:Biomaterials; Carbohydrate; Click polymerization; Polytriazole; Amides; Biomaterials; Carbohydrates; Copper compounds; Hydrocarbons; Polymerization; Regioselectivity; Bio-based monomers; Microwave assisted; Polymer backbones; Polytriazole; Random distribution; Renewable resource; Selective protection; Triazole linkages; Monomers
Año:2015
Volumen:2
Página de inicio:e70
Página de fin:e83
DOI: http://dx.doi.org/10.1016/j.mtcomm.2014.12.001
Título revista:Materials Today Communications
Título revista abreviado:Mater. Today Commun.
ISSN:23524928
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23524928_v2_n_pe70_Fidalgo

Referencias:

  • Kolb, H.C., Finn, M.G., Sharpless, K.B., (2001) Angew. Chem. Int. Ed., 40, pp. 2004-2021
  • Rostovtsev, V.V., Green, L.G., Fokin, V.V., Sharpless, K.B., (2002) Angew. Chem. Int. Ed., 41, pp. 2596-2599
  • Tornøe, C.W., Christensen, C., Meldal, M., (2002) J. Org. Chem., 67, pp. 3057-3064
  • Zeng, D., Zeglis, B., Lewis, J.S., Anderson, C.J., (2013) J. Nucl. Med., 54, pp. 829-832
  • Durmaz, H., Sanyal, A., Hizal, G., Tunca, U., (2012) Polym. Chem., 3, pp. 825-835
  • Lallana, E., Sousa-Herves, A., Fernández-Trillo, F., Riguera, R., Fernández-Megia, E., (2012) Pharm. Res., 29, pp. 1-34
  • He, H., Gao, C., (2011) Curr. Org. Chem., 15, pp. 3667-3691
  • Campidelli, S., (2011) Curr. Org. Chem., 15, pp. 1151-1159
  • Yu, H., Wang, X., (2013) Curr. Org. Chem., 17, pp. 594-609
  • Tunca, U., (2014) J. Polym. Sci. A: Polym. Chem., 52, pp. 3147-3165
  • Binder, W.H., Sachsenhofer, R., (2008) Macromol. Rapid Commun., 29, pp. 952-981
  • Binder, W.H., Sachsenhofer, R., (2007) Macromol. Rapid Commun., 28, pp. 15-54
  • Binder, W.H., Kluger, C., (2006) Curr. Org. Chem., 10, pp. 1791-1815
  • El Brahmi, N., El Kazzouli, S., Mignani, S., Bousmina, M., Majoral, J.P., (2013) Tetrahedron, 69, pp. 3103-3133
  • Pasini, D., (2013) Molecules, 18, pp. 9512-9530
  • Qin, A., Lam, J.W.Y., Tang, B.Z., (2010) Chem. Soc. Rev., 39, pp. 2522-2544
  • Aragão-Leonetti, V., Campo, V.L., Gomes, A.S., Field, R.A., Carvalho, I., (2010) Tetrahedron, 66, pp. 9475-9492
  • Besset, C., Binauld, S., Ibert, M., Fuertes, P., Pascault, J.-P., Fleury, E., Bernard, J., Drockenmuller, E., (2010) Macromolecules, 43, pp. 17-19
  • Raytchev, P.D., Besset, C., Fleury, E., Pascault, J.-P., Bernard, J., Drockenmuller, E., (2013) Pure Appl. Chem., 85, pp. 511-520
  • Besset, C., Bernard, J., Fleury, E., Pascault, J.-P., Cassagnau, P., Drockenmuller, E., Williams, R., (2010) Macromolecules, 43, pp. 5672-5678
  • Bueno, M., Molina, I., Galbis, J., (2012) Polym. Degrad. Stabil., 97, pp. 1662-1670
  • Molina-Pinilla, I., Bueno-Martínez, M., Hakkou, K., Galbis, J.A., (2014) J. Polym. Sci. A: Polym. Chem., 52, pp. 629-638
  • Kolb, H.C., Sharpless, K.B., (2003) Drug Discov. Today, 8, pp. 1128-1137
  • Angelo, N.G., Arora, P.S., (2005) J. Am. Chem. Soc., 127, pp. 17134-17135
  • Marín, R., Muñoz Guerra, S., (2009) J. Appl. Polym. Sci., 114, pp. 3723-3736
  • Salzberg, P.L., Supniewski, J.V., (1941) Org. Synth. Coll., 1, p. 119. , 7 (1927) 8
  • Osby, J.O., Martin, M.G., Ganem, B., (1984) Tetrahedron Lett., 25, pp. 2093-2096
  • (2005) APHA Standard Methods for the Examination of Water and Wastewater, , Method 3500-Cr B
  • König, W., Geiger, R., (1970) Chem. Ber., 103, pp. 788-798
  • Fuchs, M., Goessler, W., Pilger, C., Kappe, C.O., (2010) Adv. Synth. Catal., 352, pp. 323-328
  • Hartwig, S., Hecht, S., (2010) Macromolecules, 43, pp. 242-248
  • Nagao, Y., Takasu, A., (2010) J. Polym. Sci. A: Polym. Chem., 48, pp. 4207-4218
  • Al-Daraji, A.H.R., Tomi, I.H.R., (2012) Polym. Plast. Technol. Eng., 51, pp. 1327-1333

Citas:

---------- APA ----------
Fidalgo, D.M., Kolender, A.A. & Varela, O. (2015) . Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers. Materials Today Communications, 2, e70-e83.
http://dx.doi.org/10.1016/j.mtcomm.2014.12.001
---------- CHICAGO ----------
Fidalgo, D.M., Kolender, A.A., Varela, O. "Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers" . Materials Today Communications 2 (2015) : e70-e83.
http://dx.doi.org/10.1016/j.mtcomm.2014.12.001
---------- MLA ----------
Fidalgo, D.M., Kolender, A.A., Varela, O. "Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers" . Materials Today Communications, vol. 2, 2015, pp. e70-e83.
http://dx.doi.org/10.1016/j.mtcomm.2014.12.001
---------- VANCOUVER ----------
Fidalgo, D.M., Kolender, A.A., Varela, O. Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers. Mater. Today Commun. 2015;2:e70-e83.
http://dx.doi.org/10.1016/j.mtcomm.2014.12.001