Synthesis of Well-defined Poly(tetrahydrofuran)-b-Poly(a-amino acid)s via Cationic Ring-opening Polymerization (ROP) of Tetrahydrofuran and Nucleophilic ROP of N-thiocarboxyanhydrides
| Autor: | Jie Kong, Jun Ling, Peng Zhou, Xuan-Geng Dai |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
010407 polymers
Polymers and Plastics General Chemical Engineering Organic Chemistry Cationic polymerization 01 natural sciences Ring-opening polymerization Micelle 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophile Polymerization Polymer chemistry Copolymer Trifluoromethanesulfonate Tetrahydrofuran |
| Zdroj: | Chinese Journal of Polymer Science. |
| ISSN: | 1439-6203 0256-7679 |
| Popis: | The synthesis of block copolymers of poly(tetrahydrofuran)-b-poly(α-amino acid) (PTHF-b-PAA) is challenging since it is difficult to combine the two blocks produced via different/conflicting ring-opening polymerization (ROP) mechanisms. In this contribution, the cationic ROP of THF is catalyzed by rare-earth triflate [RE(OTf)3] and terminated by 2-(t-butyloxycarbonyl-amino) ethanol (BAE). After the deprotection of t-butyloxycarbonyl (Boc) group, the chain end of PTHF is quantitatively changed to amino group which thereafter initiates the nucleophilic ROP of α-amino acid N-thiocarboxyanhydrides (NTAs). Both polymerizations are well controlled, generating PTHF and PAA segments with designable molecular weights (MWs). PTHF-b-polylysine (PTHF-b-PLys) and PTHF-b-polysarcosine (PTHF-b-PSar) are obtained with MWs between 8.6 and 28.7 kg/mol. The above amphiphilic diblock copolymers form micelles in water. PTHF40-b-PSar32 acts as a surfactant to stabilize oil-in-water emulsions. Both segments of PTHF-b-PAA are biocompatible and promising in the biomedical application. |
| Databáze: | OpenAIRE |
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