Thiol-benzoxazine chemistry as a novel Thiol-X reaction for the synthesis of block copolymers |
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Authors: | Abdulrahman Musa Baris Kiskan Yusuf Yagci |
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Affiliation: | 1. Istanbul Technical University, Department of Chemistry, 34469 Maslak, Istanbul, Turkey;2. King Abdulaziz University, Center of Excellence for Advanced Materials Research and Chemistry Department, Faculty of Science, 80203, Jeddah 21589, Saudi Arabia |
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Abstract: | A novel synthetic procedure is reported for the preparation of block copolymers by means of successive 1,3-benzoxazine-thiol and Husigen type azide-alkyne coupling methodologies in one-pot and sequential synthesis. The applied 1,3-benzoxazine-thiol process based on catalytic opening of the lateral benzoxazine rings by thiols is proposed as a new thiol-X chemistry. Azide functional poly(methyl acrylate) (PMA-N3), poly(ethylene glycol) (PEG-N3) and thiol functional polystyrene (PS-SH) were prepared. The obtained PMA-N3 or PEG-N3, PS-SH and propargyl benzoxazine as a click-linker were reacted in sequential or one-pot two step manner to yield desired PS-b-PMA and PS-b-PEG block copolymer. The described thiol-benzoxazine chemistry offers a facile and efficient route to exploring the many possibilities in macromolecular synthesis. |
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Keywords: | Thiol chemistry Benzoxazine Ring-opening reaction |
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