Linear poly(amide triazole)s derived from d -glucose

Abstract

The click reaction between azides and alkynes is been increasingly employed in the preparation of polymers. In this article, we describe the synthesis and click polyaddition reaction of a new A‐B‐type amide monomer—prepared from d‐glucose as renewable resource—containing the alkyne and azide functions. Both Cu(I)‐catalyzed and metal‐free click polymerization methods were used to prepare glucose‐derived poly(amide triazole)s. The resulting polymers had weight‐average molecular weights in the 45,000–129,000 range and were characterized by GPC, IR, and NMR spectroscopies. Thermal and X‐ray diffraction studies revealed them to be amorphous. Their qualitative solubilities in various solvents and their water sorption have been studied. The poly(amide triazole)s having the alcohol functions protected as methyl ether were water‐soluble. The presence of the amide functions along the polymer chain made these polytriazoles degradable in the presence of sodium deuteroxide. The degradation was monitored by NMR analysis, and the degradation product was characterized by HRMS. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 629–638

Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers

“…However, as the poly(amide-triazole)s obtained by CuAAC polyaddition were highly insoluble in water, they were washed with an aqueous ammonium hydroxide solution, which produced an efficient removal of the metal ions, as revealed by elemental analysis and by the copper released (<0.10 ppm), determined by atomic absorption, after prolonged extraction of the polymer with water. Additionally, It has been reported that residual amounts of copper induced widening of the proton of the triazole ring and low resolution of the other signals [16]. In contrast, in our case, the 1 H NMR spectra of purified CuAAC and thermal click polymers exhibited sharp signals, with a similar width and resolution to those of monomer 7 (Fig.…”

“…Linear poly(amide-triazole)s have also been prepared http://dx.doi.org/10.1016/j.mtcomm.2014.12.001 2352-4928/© 2014 Elsevier Ltd. All rights reserved. by click polyaddition of AB-type amide monomer prepared from d-glucose [16].…”

Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose

“…S13 in ESI †) were assigned to polymer chains modied by trans-esterication with the solvent. This side-reaction on the terminal propargyl ester would prevent further polymerization, and methanolysis of the ester groups included in the backbone (Scheme 3) led to splitting of the main chain in two segments, one containing the methyl ester (11) and the other with a terminal hydroxymethylene group linked to the 1,4-disubstituted triazole (12), which accounted for the resonances at 7.73 and 4.81 ppm. The signals of polymer 6 and the terminal triazole-CH in the ester by-products indicated an approximately 1 : 1 molar ratio, revealing a high degree of transesterication in rather short-length oligomers.…”

“…The hydrophilicity endowed by the free hydroxyl groups present in native carbohydrates could be modulated by the use of protecting groups. Carbohydrate-derived linear AB polytriazoles, 9 A 2 B 2 polytriazoles, 10 AB poly(amide-triazole)s, 11,12 and A 2 B 2 poly(estertriazole)s 13,14 were mainly reported by the groups of Drockenmuller and Galbis. In a previous work, we have reported the synthesis and characterization of carbohydrate-derived poly(amide-triazole)s with the secondary hydroxyl groups protected as their methylidene acetal derivatives.…”

Degradable poly(ester triazole)s based on renewable resources

“…[17][18][19][20][21][22] However, in the case of the synthesis of linear triazole-linked polymers it has been more limited. In this respect, polyaddition of small bis-azide and bis-alkyne monomers has been used for the preparation of different polytriazoles by us [23][24][25] and others. [26][27][28][29][30][31][32][33][34] We are particularly interested in degradable materials, such as poIy(ester triazole)s. Polyesters constitute one of the largest classes of biodegradable materials, with very well-known examples, such as polylactide and polycaprolactone.…”