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Facile fabrication of polymer network using click chemistry and their computational study.

ABSTRACT: Click reaction is a very fast, high yield with no by-product, biocompatible, tolerant to surrounded medium, and very specific cycloaddition reaction between azides and alkynes to form triazole. They are widely being employed in the synthesis of various polymeric materials. Here, the design, fabrication and characterization of hydrogel prepared using click reaction have been reported. At first, telechelic acetylene precursor for click reaction is prepared from diisocyanatohexane and propargyl alcohol in the presence of triethylamine. The azide derivatives of poly(hydroxyethylmethacrylate), i.e. poly(HEMA), are successfully prepared following two different routes. In route 1, esterification of bromopropionic acid is performed with HEMA monomer using N,N'-dicyclohexylcarbodiimide/4-dimethylaminopyridine (DCC/DMAP) as a catalyst followed by replacing bromide by azide moiety. Free radical polymerization of the fabricated monomer is then performed under N₂ atmosphere using azobisisobutyronitrile (AIBN) as an initiator. In route 2, polymerization of HEMA has been carried out first, then modification of the polymer with azide group via successive steps to obtain azide derivative polymer for click reaction. The hydrogel is prepared by a very fast, highly specific, and simple click reaction between azide derivative polymer and telechelic acetylene precursor using copper as a catalyst. The structures of derivatives of azide-functionalized HEMA, acetylene precursors and hydrogels are confirmed by FTIR and ¹H-NMR spectroscopy. The optimized structure of each precursor is determined, and their chemical and thermodynamic parameters are computationally studied in detail.

SUBMITTER: Ahmed MK

PROVIDER: S-EPMC8074938 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:How to maximize the number of desirable active sites on the surface of the catalyst and minimize the number of sites promoting undesirable side reactions is currently an important research topic. In this study, a new way based on the synergism to achieve the successful fabrication of an ordered heterobimetallic self-assembled monolayer (denoted as BMSAM) with a controlled composition and an excellent orientation of metals in the monolayer was developed. BMSAM consisting of phenanthroline and Schiff-base groups was prepared, and its novel heterobimetallic (Cu and Pd) self-assembled monolayer anchored in silicon (denoted as Si-Fmp-Cu-Pd BMSAM) with a controlled composition and a fixed position was fabricated and characterized by UV, cyclic voltammetry, Raman, X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), X-ray diffraction (XRD), inductively coupled plasma atomic emission spectroscopy (ICP-AES), and water-drop contact angle (WDCA) analyses. The effects of Si-Fmp-Cu-Pd BMSAM on its catalytic properties were also systematically investigated using "click" reaction as a template by WDCA, XPS, SEM, XRD, ICP-AES and in situ Fourier transform infrared analyses in a heterogeneous system. The results showed that the excellent catalytic characteristic could be attributed to the partial (ordered or proper distance) isolation of active sites displaying high densities of specific atomic ensembles. The catalytic reaction mechanism of the click reaction interpreted that the catalytic process mainly occurred on the surface of the monolayer, internal active site (Pd) and rationalized that the Cu(I) species and Pd(0) reduced from the Cu(II) and Pd(II) catalyst were active species, which had a proper distance between two different metals. The cuprate-triazole intermediate and the palladium intermediate, whose production is the key step, should lie in a proper position between the copper and active palladium sites, with which the reaction rate of transmetalation would be improved to increase the amount of the undesired Sonogashira coupling product.

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Facile fabrication of polymer network using click chemistry and their computational study.

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