Synthesis of Well-defined Poly(tetrahydrofuran)-<italic style="font-style: italic">b</italic>-Poly(<italic style="font-style: italic">α</italic>-amino acid)s <italic style="font-style: italic">via</italic> Cationic Ring-opening Polymerization (ROP) of Tetrahydrofuran and Nucleophilic ROP of <italic style="font-style: italic">N</italic>-thiocarboxyanhydrides

Peng Zhou; Xuan-Geng Dai; Jie Kong; Jun Ling

doi:10.1007/s10118-021-2539-6

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Synthesis of Well-defined Poly(tetrahydrofuran)-b-Poly(α-amino acid)s via Cationic Ring-opening Polymerization (ROP) of Tetrahydrofuran and Nucleophilic ROP of N-thiocarboxyanhydrides

ARTICLE | Updated：2021-01-05

- Synthesis of Well-defined Poly(tetrahydrofuran)-b-Poly(α-amino acid)s via Cationic Ring-opening Polymerization (ROP) of Tetrahydrofuran and Nucleophilic ROP of N-thiocarboxyanhydrides
- Chinese Journal of Polymer Science Vol. 39, Issue 6, Pages: 702-708(2021)
- Affiliations：
  
  a.Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
  b.Shaanxi Key Laboratory of Macromolecular Science and Technology, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an 710072, China
- Author bio：
  
  kongjie@nwpu.edu.cn (J.K.)
  lingjun@zju.edu.cn (J.L.)
- Funds：
- DOI：10.1007/s10118-021-2539-6
  CLC：
- Received：02 November 2020，
  
  Revised：2020-11-30，
  
  Accepted：07 December 2020，
  
  Online First：05 January 2021，
  
  Published：15 April 2021
- Accepted：
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Zhou, P.; Dai, X. G.; Kong, J.; Ling, J. Synthesis of well-defined poly(tetrahydrofuran)-, b,-poly(, α,-amino acid)s , via, cationic ring-opening polymerization (ROP) of tetrahydrofuran and nucleophilic ROP of , N,-thiocarboxyanhydrides. Chinese J. Polym. Sci. 2021, 39, 702–708

Peng Zhou, Xuan-Geng Dai, Jie Kong, et al. Synthesis of Well-defined Poly(tetrahydrofuran)-b-Poly(α-amino acid)s via Cationic Ring-opening Polymerization (ROP) of Tetrahydrofuran and Nucleophilic ROP of N-thiocarboxyanhydrides[J]. Chinese Journal of Polymer Science, 2021, 39(6): 702-708. DOI: 10.1007/s10118-021-2539-6.
Zhou, P.; Dai, X. G.; Kong, J.; Ling, J. Synthesis of well-defined poly(tetrahydrofuran)-, b,-poly(, α,-amino acid)s , via, cationic ring-opening polymerization (ROP) of tetrahydrofuran and nucleophilic ROP of , N,-thiocarboxyanhydrides. Chinese J. Polym. Sci. 2021, 39, 702–708 DOI： 10.1007/s10118-021-2539-6.

Peng Zhou, Xuan-Geng Dai, Jie Kong, et al. Synthesis of Well-defined Poly(tetrahydrofuran)-b-Poly(α-amino acid)s via Cationic Ring-opening Polymerization (ROP) of Tetrahydrofuran and Nucleophilic ROP of N-thiocarboxyanhydrides[J]. Chinese Journal of Polymer Science, 2021, 39(6): 702-708. DOI: 10.1007/s10118-021-2539-6. DOI：

摘要

Abstract

The synthesis of block copolymers of poly(tetrahydrofuran)-

-poly(

-amino acid) (PTHF-

-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)

] and terminated by 2-(

-butyloxycarbonyl-amino) ethanol (BAE). After the deprotection of

-butyloxycarbonyl (Boc) group

the chain end of PTHF is quantitatively changed to amino group which thereafter initiates the nucleophilic ROP of

-amino acid

-thiocarboxyanhydrides (NTAs). Both polymerizations are well controlled

generating PTHF and PAA segments with designable molecular weights (MWs). PTHF-

-polylysine (PTHF-

-PLys) and PTHF-

-polysarcosine (PTHF-

-PSar) are obtained with MWs between 8.6 and 28.7 kg/mol. The above amphiphilic diblock copolymers form micelles in water. PTHF

-PSar

acts as a surfactant to stabilize oil-in-water emulsions. Both segments of PTHF-

-PAA are biocompatible and promising in the biomedical application.

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Synthesis of Well-defined Poly(tetrahydrofuran)-b-Poly(α-amino acid)s via Cationic Ring-opening Polymerization (ROP) of Tetrahydrofuran and Nucleophilic ROP of N-thiocarboxyanhydrides

DOI：10.1007/s10118-021-2539-6

摘要

Abstract

关键词

Keywords

references