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Facile Synthesis of Optically Active and Magnetic Nanoparticles Carrying Helical Poly(phenyl isocyanide) Arms and Their Application in Enantioselective Crystallization
Author(s) -
Lin YaLan,
Chu JiaHong,
Lu HaoJun,
Liu Na,
Wu ZongQuan
Publication year - 2018
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.201700685
Subject(s) - enantioselective synthesis , nanoparticle , materials science , crystallization , enantiopure drug , magnetic nanoparticles , enantiomer , grafting , enantiomeric excess , combinatorial chemistry , chemical engineering , polymer chemistry , polymer , nanotechnology , organic chemistry , chemistry , catalysis , composite material , engineering
In this paper, the facile synthesis of hybrid Fe 3 O 4 magnetic nanoparticles carrying helical poly(phenyl isocyanide) (PPI) arms via both “grafting from” and “grafting onto” strategies is reported. First, alkyne‐Pd(II) catalysts are anchored onto the surface of the Fe 3 O 4 magnetic nanoparticle, which promote the polymerization of enantiopure phenyl isocyanide, affording the expected hybrid magnetic nanoparticle with Fe 3 O 4 in core and helical PPI as arms. The nanoparticle also exhibits highly optical activity due to the excess of one‐handed helicity of the PPI arms. Moreover, the hybrid magnetic nanoparticle can be alternatively synthesized via “grafting onto” strategy. A triethoxysilanyl‐terminated single handed helical PPI bearing l ‐alanine ester pendants is prepared and grafted onto the surface of Fe 3 O 4 nanoparticle. The generated hybrid magnetic nanoparticles show both magnetic character and optical activity. Taking advantage of these properties, they can be used in enantioselective crystallization of racemic threonine. The enantiomeric excess ( ee ) of the induced crystals is up to 93%. Moreover, the nanoparticles can be facilely recovered and recycle used for at least four times in enantioselective crystallization without significantly loss of its enantioselectivity.