Facile fabrication of polymer network using click chemistry and their computational study
| Autor: | Abu Bin Imran, Md. Kausar Ahmed, Ajoy Kumer |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
HOMO
LUMO Materials science Fabrication Triazole 02 engineering and technology 010402 general chemistry 01 natural sciences chemistry.chemical_compound azide acetylene lcsh:Science HOMO/LUMO Research Articles Multidisciplinary 021001 nanoscience & nanotechnology Combinatorial chemistry Cycloaddition 0104 chemical sciences Chemistry Acetylene chemistry Yield (chemistry) Click chemistry lcsh:Q Azide hydrogel click reaction 0210 nano-technology |
| Zdroj: | Royal Society Open Science Royal Society Open Science, Vol 8, Iss 3 (2021) |
| ISSN: | 2054-5703 |
| DOI: | 10.1098/rsos.202056 |
| Popis: | 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 N 2 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 1 H-NMR spectroscopy. The optimized structure of each precursor is determined, and their chemical and thermodynamic parameters are computationally studied in detail. |
| Databáze: | OpenAIRE |
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