Synthesis of an azide–thiol linker for heterogeneous polymer functionalization via the “click” reaction

In this study, the synthesis of a telechelic linker bearing both azide and thiol functional groups was described. The reaction conditions were investigated to optimize the reaction yield. The product was analyzed using thin layer chromatography (TLC) and proton nuclear magnetic resonance (1 H NMR). | Journal of Science and Technology 55 (1B) (2017) 152–159 SYNTHESIS OF AN AZIDE–THIOL LINKER FOR HETEROGENEOUS POLYMER FUNCTIONALIZATION VIA THE “CLICK” REACTION Thuy Thu Truong1, Ha Tran Nguyen1, 2, * 1 Faculty of Materials Technology, HCMUT–VNUHCM 268 Ly Thuong Kiet Street, Ward 14, District 10, Ho Chi Minh City, Vietnam 2 Materials Technology Key Laboratory, HCMUT–VNUHCM 268 Ly Thuong Kiet Street, Ward 14, District 10, Ho Chi Minh City, Vietnam * Email: nguyentranha@ Received: 30 December 2016; Accepted for publication: 3 March 2017 ABSTRACT In this study, the synthesis of a telechelic linker bearing both azide and thiol functional groups was described. The reaction conditions were investigated to optimize the reaction yield. The product was analyzed using thin layer chromatography (TLC) and proton nuclear magnetic resonance (1H NMR). The employment of the obtained azide–thiol linker in heterogeneous polymer “click” functionalization was demonstrated for the first time, which was monitored by an online FT–IR method. The obtained telechelic azide–thiol linker is envisioned to be useful chemical tools to link macromolecular chains via orthogonal click reactions. Keywords: azide, thiol, “click” reaction, polymer functionalization. 1. INTRODUCTION Organic azides are well–known as an important and versatile class of chemical compounds. They are considered as powerful precursors for reactive species such as nitrenes, aziridines, triazoles, triazolines and many others, as well as can be easily transformed into amines, isocyanates and other functional groups [1]. Especially, they have received significantly increasing interest as valuable and versatile reagents within the concepts of “click” chemistry. In the “click” chemistry aspect, organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science [1]. Click chemistry has become the catchphrase whenever conjugation of different molecules to .

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