Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (3): 280-292.DOI: 10.11944/j.issn.1000-0518.2020.03.190253

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

LI Maoshengab,CHEN Jinlonga,TAO Youhuaa*()   

  1. 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
  • Accepted:2019-11-07 Online:2020-03-01 Published:2020-03-10
  • Contact: TAO Youhua
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.21805272), and the Jilin Science and Technology Bureau(No.20180201070GX)

Abstract:

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 monomers 1 and 2 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.

Key words: amino acid-bearing polymers, ring-opening metathesis polymerization, regio- and stereoselectivity, block copolymers, reverse micelles