Citation: LI Maosheng, CHEN Jinlong, TAO Youhua. Regio- and Stereoselective Ring-Opening Metathesis Polymerization of Amino Acid Functionalized Cyclooctenes[J]. Chinese Journal of Applied Chemistry, ;2020, 37(3): 280-292. doi: 10.11944/j.issn.1000-0518.2020.03.190253 shu

Regio- and Stereoselective Ring-Opening Metathesis Polymerization of Amino Acid Functionalized Cyclooctenes

a.
Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.
University of the Chinese Academy of Sciences, Beijing 100039, China

Corresponding author: TAO Youhua, youhua.tao@ciac.ac.cn
Received Date: 25 September 2019
Revised Date: 11 October 2019
Accepted Date: 7 November 2019

Fund Project: the National Natural Science Foundation of China 21805272the Jilin Science and Technology Bureau 20180201070GXSupported by the National Natural Science Foundation of China(No.21805272), and the Jilin Science and Technology Bureau(No.20180201070GX)

Figures(9)

Synthesis of side-chain amino acid-bearing polymers with controllable primary structures is still a long-term challenge in polymer chemistry compared to biomacromolecules (such as proteins and DNA) with completely precise microstructures. Here, we describe the synthesis of high trans-stereoregular (>99%) and high head-to-tail regioregularity (>99%) leucine-based homopolymers and block copolymers with relatively low polydispersities ranging from 1.3 to 1.6, using two designed monomers, namely (cyclooct-2-ene-1-carbonyl)-L-leucine methyl ester (1) and (cyclooct-2-ene-1-carbonyl)-L-leucine (2), via Grubbs 2nd catalyst at mild conditions. Importantly, the block copolymer of monomers1 and2 with molar ratio n(1):n(2)=50:50 is soluble in acetone to form reverse micelles with radius around 30 nm, which is composed of a hydrophilic core of poly(2) and a hydrophobic shell of poly(1). However, the random copolymers with the same proportion was partially insoluble in the solvent. These amino acid-bearing polymers with well-defined regio-/stereoregular structures provide the basis for relevant applications in biomimetic materials.
- amino acid-bearing polymers,
- ring-opening metathesis polymerization,
- regio- and stereoselectivity,
- block copolymers,
- reverse micelles
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