Issue 27, 2021

POSS-based starlike hybrid helical poly(phenyl isocyanide)s: their synthesis, self-assembly, and enantioselective crystallization ability

Abstract

Polyhedral oligomeric silsesquioxane (POSS) based starlike hybrid helical poly(phenyl isocyanide)s (PPIs) with well-defined structures were designed and prepared in this contribution. The POSS modified with Pd(II) complexes (POSS-Pd(II)) was firstly obtained. Then well-defined starlike hybrid helical PPIs with POSS cores were synthesized through the polymerization of phenyl isocyanide monomers using POSS-Pd(II) as the initiator. The polymerization proceeded in a living and controlled manner. Meanwhile, polymerization of chiral phenyl isocyanides with decyl chain modified pendant L- or D-alanine afforded optically active hybrid starlike helical PPIs with preferred handedness. What's more, amphiphilic starlike hybrid helical PPI block copolymers showing thermoresponses were easily obtained, and their self-assembly and thermo-responsive behaviours were studied. In addition, cross-linked hybrid helical PPIs were obtained via the transesterification reaction between pentafluorophenyl ester and cystamine. Benefitting from the essential chirality of the handed helical PPIs, the cross-linked hybrid PPIs showed excellent ability in the enantioselective crystallization of racemic compounds. The enantiomeric excess (ee) of the induced crystal of threonine could be up to 95%.

Graphical abstract: POSS-based starlike hybrid helical poly(phenyl isocyanide)s: their synthesis, self-assembly, and enantioselective crystallization ability

Supplementary files

Article information

Article type
Paper
Submitted
11 May 2021
Accepted
16 Jun 2021
First published
17 Jun 2021

Polym. Chem., 2021,12, 3917-3924

POSS-based starlike hybrid helical poly(phenyl isocyanide)s: their synthesis, self-assembly, and enantioselective crystallization ability

H. Zou, Q. Li, Q. Wu, W. Liang, X. Hou, L. Zhou, N. Liu and Z. Wu, Polym. Chem., 2021, 12, 3917 DOI: 10.1039/D1PY00639H

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