Sodium 3-azidopropyldialkoxysilanolate - A versatile route towards new functional 1,2,3–triazole based hyperbranched polyorganoalkoxysiloxanes

Migulin, Dmitry A.; Milenin, Sergey A.; Cherkaev, G. V.; Zezin, A. B.; Zezina, Elena A.; Музафаров, А. М.

doi:10.1016/j.reactfunctpolym.2020.104648

Cited by 12 publications

(18 citation statements)

References 34 publications

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“…Synthesis and characterization of hyperbranched 1,2,3-triazole based organoethoxysiloxane polymers Two types polymers, namely, water-soluble DMA-1,2,3-triazolesiloxane and water insoluble PY-1,2,3-triazole-siloxane functional polymers, were obtained in the CuAAC reaction between earlier reported hyperbranched 3-azidopropylethoxysiloxanes (N 3siloxane) 11 and 1,1-dimethylpropargylamine and 2-ethynylpyridine, respectively, in the presence of a catalytic amount of CuI (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

“…Hyperbranched poly-3-azidopropylethoxysiloxane was synthesized according to the procedure described previously. 11 1 H-NMR (300 MHz, CDCl 3 ) δ : 3.79 (m, 2H), 3.25 (m, 2H), 1.67 (m, 2H), 1.20 (m, 3H), 0.67 (m, 2H); 13 C NMR (75 MHz, CDCl 3 ) δ 58.24, 53.55, 22.50, 18.03, (10.31, 9.61, 9.45, 9.24, 9.19, 9.13, 9.07, 8.97, 8.44, 8.16); 29 Si-NMR (60 MHz, CDCl 3 ), δ : (−49.3)–(−51.6) (R-Si(OCH 2 CH 3 ) 2 O 0.5 ), (−52.1)–(54.4), (R-Si(O CH 2 CH 3 )O), (−65.4)–(−70.0) (R-SiO 1.5 ). GPC: M w = 1696 g mol −1 , M w / M n = 1.13.…”

Section: Methodsmentioning

confidence: 99%

“…Regarding these excellent properties, a number of research studies were specifically dedicated to that class of polymers. [7][8][9][10] In our previous work a versatile method towards the preparation of hyperbranched 3-azidopropylalkoxysiloxane polymers 11 capable of undergoing functional derivatization through a well-known copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) ''click-reaction'' process 12 while preserving its functional hyperbranched alkoxysiloxane molecular structure was developed.…”

Section: Introductionmentioning

confidence: 99%

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New types of hyperbranched 1,2,3-triazole-alkoxysiloxane functional polymers for metal embedded nanocomposite surface coatings

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New types of hyperbranched 1,2,3-triazole-alkoxysiloxane functional polymers for metal embedded nanocomposite surface coatings

et al. 2022

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“…Bretzle et al obtained PDMS with functional azido groups from epoxides preliminarily incorporated into the PDMS structure by the hydrosilylation reaction . It should also be noted that at the moment, work has been carried out on the synthesis of azidoalkylsiloxanes of nonlinear structure. − …”

Section: Results and Discussionmentioning

confidence: 99%

Acid-Catalyzed Rearrangement of Azidopropyl-Siloxane Monomers for the Synthesis of Azidopropyl-Polydimethylsiloxane and Their Carboxylic Acid Derivatives

et al. 2021

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In this work, we were the first to show the possibility of synthesizing polydimethylsiloxanes (PDMSs) with azidopropyl-functional groups at the silicon atom by the classical methods for PDMS synthesis, that is, ring-opening polymerization (ROP) and catalytic rearrangement of siloxanes in the presence of a strong acid (CF3SO3H). The suggested method was used to obtain PDMSs containing azidopropyl-functional groups at both ends of the polymer chain (telechelics) as well as PDMSs with irregular structures containing different fractions (5–50%) of azidopropyl-functional groups in the main polymer chain. The suggested method also proved to be efficient for synthesizing PDMSs containing both azidopropyl- and hydridosilyl-functional groups simultaneously. As a result, PDMSs with different mutual arrangements of two types of functional groups along the PDMS chain were obtained. The method for the catalytic rearrangement of low-molecular-weight siloxanes that we used made it possible to obtain azidopropyl-functional PDMSs in a wide range of molecular weights from 2000 to 88,000 according to gel permeation chromatography (GPC) data. The possibility of further modification of the resulting azidopropyl-functional PDMS, as well as multifunctional PDMSs containing azidopropyl- and hydridosilyl-functional groups simultaneously, by azide-alkyne cycloaddition reactions was demonstrated. The polymers obtained were characterized by 1H and 29Si NMR spectroscopy and by GPC.

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“…The click reaction of azide–alkyne cycloaddition is one of the simplest ways in terms of implementation, tolerant to the presence of various functional groups and easily passing on most substrates. Originally it was discovered as the Huisgen reaction and then improved by the Meldal and Sharpless groups to metal-catalyzed 1,3-dipolar cycloaddition chemistry; this reaction has gained enormous importance in many areas of organic chemistry, including polymer chemistry. , Recently, more and more publications have appeared on the introduction of azide and ethynyl functional groups into the structure of polyorganosiloxanes and their postpolymerization modification according to the reaction mechanism of metal-catalyzed 1,3-dipolar cycloaddition chemistry. − However, at the present stage of development of this direction, the possibilities of functionalization of such polyorganosiloxanes are insufficiently developed, which may be due to the unavailability of a wide range of initial polymers with azide or ethynyl groups.…”

Section: Introductionmentioning

confidence: 99%

Environment Friendly Process toward Functional Polyorganosiloxanes with Different Chemical Structures through CuAAC Reaction

Bezlepkina

Ardabevskaia

Klokova

et al. 2022

ACS Appl. Polym. Mater.

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Despite the presence of many methods, which were created to date for the preparation, functionalization, and vulcanization of polysiloxanes, the development of materials based on silicones remains relevant and requires the introduction of new approaches that combine such modern strategies as atom-economical reactions, refusal to use harmful and dangerous organochlorosilanes, and using the principles of green chemistry and minimizing the use of solvents. In this work, we develop modern approaches to the preparation of both linear and branched polyorganosiloxanes containing azidopropyl functions at the silicon atom. In the first part of the work, it was shown that the proposed method for introducing these groups by catalytic rearrangement with the opening of cyclosiloxane is effective and makes it possible to obtain polysiloxanes with different contents of azidopropyl groups and different molecular weights. The second part of the work demonstrated the possibility of postpolymerization functionalization of such polymers by the mechanism of azide–alkyne cycloaddition under “green” conditions, without using solvents and amines. All of the most important functional fragments were introduced into the structures of organosilicon polymers by a single mechanism, under simple conditions, without the use of expensive catalysts, exposure to irradiation, and hazardous solvents. The combination of simplicity and versatility in the preparation of polysiloxanes with azidopropyl groups with the possibility of performing a click reaction makes it possible to directionally obtain the required materials based on universal raw materials and, as a result, can open up broad prospects for serious development and rethinking of the chemistry of silicones.

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Sodium 3-azidopropyldialkoxysilanolate - A versatile route towards new functional 1,2,3–triazole based hyperbranched polyorganoalkoxysiloxanes

Cited by 12 publications

References 34 publications

New types of hyperbranched 1,2,3-triazole-alkoxysiloxane functional polymers for metal embedded nanocomposite surface coatings

New types of hyperbranched 1,2,3-triazole-alkoxysiloxane functional polymers for metal embedded nanocomposite surface coatings

Acid-Catalyzed Rearrangement of Azidopropyl-Siloxane Monomers for the Synthesis of Azidopropyl-Polydimethylsiloxane and Their Carboxylic Acid Derivatives

Environment Friendly Process toward Functional Polyorganosiloxanes with Different Chemical Structures through CuAAC Reaction

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