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Issue 14, 2017
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Facile synthesis and chiral recognition of block and star copolymers containing stereoregular helical poly(phenyl isocyanide) and polyethylene glycol blocks

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Abstract

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 nanoparticles 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.

Graphical abstract: Facile synthesis and chiral recognition of block and star copolymers containing stereoregular helical poly(phenyl isocyanide) and polyethylene glycol blocks

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Publication details

The article was received on 06 Jan 2017, accepted on 08 Mar 2017 and first published on 09 Mar 2017


Article type: Paper
DOI: 10.1039/C7PY00028F
Citation: Polym. Chem., 2017,8, 2152-2163
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    Facile synthesis and chiral recognition of block and star copolymers containing stereoregular helical poly(phenyl isocyanide) and polyethylene glycol blocks

    N. Liu, C. Ma, R. Sun, J. Huang, C. Li and Z. Wu, Polym. Chem., 2017, 8, 2152
    DOI: 10.1039/C7PY00028F

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