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Synthesis of Thiol-functional telechelic Polycaprolactone via Thiol-michael reaction

Functional polycaprolactones (PCL) have great potential for opening a new frontier in material design. We report here a method for preparing a thiol end-functionalized telechelic polycaprolactone using a straightforward and highly efficient process via the thiol-acrylate Micheal click addition reaction. Firstly, we esterified PCL diol with excess amount of acryloyl chloride resulting acrylate- end capped polycaprolactone (PCL-diacrylate). Then, thiol-end capped polycaprolactone (PCL-dithiol) was prepared by the reaction between 2,2′- (ethylenedioxy)diethanethiol and PCL-diacrylate in the present of base catalyst (Thiol-ene reaction). Both steps were carried out in the mild condition with high yield. The obtained product was structural analyzed using 1H NMR spectroscopy. | Synthesis of Thiol-functional telechelic Polycaprolactone via Thiol-michael reaction