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Abstract:

1,6-Diaminohexane and a 2-(S)-hydroxypentanedioic acid 5,2-lactone derivative (3) were polycondensed to afford an aregic polyamide 4. A chiral monomer (5) having a 2-fold axis of symmetry was chemoselectively constructed from 3, and upon polymerization with the diamine led to an AABB-type polyamide having a syndioregic orientation of the hydroxyl substituents. The analogous isoregic polyamide 11 was also prepared. The three polymers had the same basic structure, but they differ in their regio and stereoregularity. These polyamides, which displayed optical activity, were characterized by IR and 1H and 13C NMR, and their molecular weights were estimated by GPC, viscosimetry, and matrix-assited ultraviolet laser desorption/ionization time-of-flight mass spectrometry (UV-MALDI-TOF MS). This technique was particularly convenient to confirm the repeat units and to detect the functional groups at both ends of the chains. In accordance with their growth processes polyamides 11 and 12 showed the typical UV-MALDI-TOF spectrum for homopolymerization, and polyamides 4 and 6 showed those corresponding to growing by copolymerization. Besides, in agreement with their stereoregularity, polyamides 6 and 11 showed better crystalline properties than those of 4.

Registro:

Documento: Artículo
Título:Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity
Autor:Orgueira, H.A.; Erra-Balsells, R.; Nonami, H.; Varela, O.
Ciudad:Washington, DC, United States
Filiación:Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Plant Biophys./Biochem. Res. Lab., College of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama 790-8066, Japan
Palabras clave:Copolymerization; Crystal orientation; Crystal symmetry; Crystalline materials; Homopolymerization; Infrared spectroscopy; Mass spectrometry; Molecular weight; Monomers; Polycondensation; Synthesis (chemical); Viscosity measurement; Stereoregularity; Syndioregic orientations; Polyamides
Año:2001
Volumen:34
Número:4
Página de inicio:687
Página de fin:695
DOI: http://dx.doi.org/10.1021/ma000016+
Título revista:Macromolecules
Título revista abreviado:Macromolecules
ISSN:00249297
CODEN:MAMOB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00249297_v34_n4_p687_Orgueira

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Citas:

---------- APA ----------
Orgueira, H.A., Erra-Balsells, R., Nonami, H. & Varela, O. (2001) . Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity. Macromolecules, 34(4), 687-695.
http://dx.doi.org/10.1021/ma000016+
---------- CHICAGO ----------
Orgueira, H.A., Erra-Balsells, R., Nonami, H., Varela, O. "Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity" . Macromolecules 34, no. 4 (2001) : 687-695.
http://dx.doi.org/10.1021/ma000016+
---------- MLA ----------
Orgueira, H.A., Erra-Balsells, R., Nonami, H., Varela, O. "Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity" . Macromolecules, vol. 34, no. 4, 2001, pp. 687-695.
http://dx.doi.org/10.1021/ma000016+
---------- VANCOUVER ----------
Orgueira, H.A., Erra-Balsells, R., Nonami, H., Varela, O. Synthesis of chiral polyhydroxy polyamides having chains of defined regio and stereoregularity. Macromolecules. 2001;34(4):687-695.
http://dx.doi.org/10.1021/ma000016+