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

Citation

Imran, Abu Bin; Ahmed, Md. Kausar; Kumer, Ajoy (2021), Facile fabrication of polymer network using click chemistry and their computational study , Dryad, Dataset, https://doi.org/10.5061/dryad.5x69p8d1v

Abstract

Click reaction is a very fast, high yield with no byproduct, 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.

Methods

Fourier transform infrared (FT-IR) spectrophotometer (FTIR-8400, Shimadzu, Japan)

400 MHz Bruker BPX-400, 1HNMR spectrometer

Thermogravimetry-Differential Scanning Calorimetry (STA/TG-DSC) of STA 449 F3 Jupiter®, NETZSCH-Gerätebau GmbH, Germany

The VAMP code of Material studio version 8.0 was employed for optimization and calculation based on DFT

Funding

Grant of Advanced Research in Education (GARE) from the Ministry of Education, the Peoples Republic of Bangladesh, Award: PS2016239

Grant of Advanced Research in Education (GARE) from the Ministry of Education, the Peoples Republic of Bangladesh, Award: PS2016239