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Synthesis of Unimolecular Micelles with Incorporated Hyperbranched Boltorn H30 Polyester modified with Hyperbranched Helical Poly(phenyl isocyanide) Chains and their Enantioselective Crystallization Performance
Author(s) -
Zhang ZhiHuang,
Qiao ChenYang,
Zhang Jian,
Zhang WenMing,
Yin Jun,
Wu ZongQuan
Publication year - 2017
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201700315
Subject(s) - enantioselective synthesis , materials science , micelle , polymer chemistry , crystallization , chirality (physics) , monomer , polymerization , enantiomer , ring opening polymerization , polymer , chemistry , organic chemistry , catalysis , aqueous solution , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , composite material , quark
Here, the fabrication of unimolecular micelles functionalized with helical polymeric chains as a chiral nucleating agent in enantioselective crystallization is reported. Starting from a fractionated hyperbranched polyester (Boltorn H30), the ring‐opening polymerization of l ‐lactic acid (LLA) and subsequent terminal‐group modification affords the alkyne‐Pd(II)‐anchored hyperbranched macroinitiator (H30‐PLLA‐Pd). By taking advantage of a Pd(II)‐catalyzed living polymerization of chiral pendant modified l ‐ or d ‐phenyl isocyanide (PI) monomers, well‐defined chiral unimolecular micelles (H30‐PLLA‐PPI) grafted with radiating helical PPI coronas of one predominant screw sense are obtained. The resultant chiral materials demonstrate excellent application in the enantioselective crystallization of racemic threonine in water, and a 92% enantiomeric excess value of the residual solution is obtained. It is believed this present proof of concept and methodology are facile and powerful for preparing novel and versatile chiral materials with different topological structures, not only applicable to PPI but also to other types of polymers.