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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
Chinese Journal of Polymer Science ( IF 4.1 ) Pub Date : 2021-01-05 , DOI: 10.1007/s10118-021-2539-6
Peng Zhou , Xuan-Geng Dai , Jie Kong , Jun Ling

The synthesis of block copolymers of poly(tetrahydrofuran)-b-poly(a-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 a-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.



中文翻译:

通过四氢呋喃的阳离子开环聚合(ROP)和N-硫代羧酸酐的亲核ROP合成定义明确的聚四氢呋喃b-聚a氨基酸

聚的嵌段共聚物的合成(四氢呋喃) - b -聚(一个氨基酸)(PTHF- b -PAA)是具有挑战性的,因为它是难以生产的两个块合并通过不同/冲突的开环聚合(ROP)机制。在这种贡献中,THF的阳离子ROP被稀土三氟甲磺酸盐[RE(OTf)3 ]催化,并被2-(丁氧羰基氨基)乙醇(BAE)终止。的脱保护后丁氧基羰(Boc)基团,PTHF的链端定量改变为氨基其中此后发起的亲核ROP一个α-氨基酸Ñ-硫代羧酸酐(NTA)。两种聚合均受到良好控制,生成具有可设计分子量(MWs)的PTHF和PAA链段。获得MW为8.6至28.7kg / mol的PTHF- b-聚赖氨酸(PTHF- b- PLys)和PTHF- b-聚肌氨酸(PTHF- b- PSar)。上述两亲性二嵌段共聚物在水中形成胶束。PTHF 40 - b -PSar 32用作表面活性剂以稳定水包油乳液。PTHF- b- PAA的两个片段都是生物相容的,在生物医学应用中很有前途。

更新日期:2021-01-08
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