期刊
POLYMER CHEMISTRY
卷 8, 期 14, 页码 2152-2163出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7py00028f
关键词
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资金
- National Natural Scientific Foundation of China [21574036, 51673057, 21622402]
- 1000plan Program for Young Talents of China
- Open Project of State Key Laboratory of Supramolecular Structure and Materials [sklssm201624]
A new Pd(II) initiator bearing an alkyne headgroup was designed and synthesized. Living polymerization of phenyl isocyanide using this Pd(II) initiator afforded well-defined alkyne-terminated helical poly(phenyl isocyanide) (PPI) with controlled molecular weights (Mns) and narrow molecular weight distributions (Mw/Mns). The alkyne end group of PPI coupled with azide-terminated random-coil poly(ethylene glycol) (PEG) via copper-catalyzed alkyne-azide cycloaddition (CuAAC) click chemistry formed a novel class of helix-coil block copolymer PPI-b-PEG. The alkyne-terminated PPI coupled with a PEG bearing azides on both the two chain ends afforded a helix-coil-helix triblock copolymer PPI-b-PEG-b-PPI. When optically active alkyne-terminated PPIs bearing L-or D-menthol ester pendants were used in the coupling reaction, optically active di-and triblock copolymers were facilely achieved, which exhibited an intense Cotton effect on circular dichroism (CD) spectra due to the one-handed helical conformation of the PPI segments. Moreover, a Pd(II) complex bearing two alkyne headgroups was designed and synthesized, which initiated the living polymerization of phenyl isocyanide that lead to the formation of well-defined PPI with two alkyne groups on the same chain end. Coupling this helical polymer with azide-terminated PEG via CuAAC click chemistry formed a helix-(coil)(2) miktoarm star copolymer containing two random-coil PEG segments and one helical PPI block. The amphiphilic block and star polymers containing hydrophobic PPI and hydrophilic PEG segments were found to self-assemble into well-defined spherical nano-particles in water. Interestingly, these supramolecular architectures showed excellent chiral recognition to dansyl modified L-and D-phenylalanine (L-or D-Phe-DNSP) in high enantiomeric selectivity.
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