Optically Active Porous Microspheres Consisting of Helical Substituted Polyacetylene Prepared by Precipitation Polymerization without Porogen and the Application in Enantioselective Crystallization

Chen, Chunni; Zhao, Biao; Deng, Jianping

doi:10.1021/acsmacrolett.5b00088

Cited by 18 publications

(23 citation statements)

References 54 publications

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“…Triton X‐100 (polyethylene glycol tert‐octylphenyl ether) and [(nbd)RhCl] 2 were purchased from Alfa Aesar and used as received without further purification. ACA and M1 were synthesized according to earlier reports. All the other reagents were used as received.…”

Section: Methodsmentioning

confidence: 99%

“…To develop novel chiral polymeric materials derived from CA, we recently began our efforts along this interesting research direction. In our previous study, chiral acetylenic monomer derived from cholic acid (ACA) was synthesized and then successfully underwent precipitation polymerization, thereby providing chirally helical polymer microspheres with intriguing porous structure . Given the fact of high cost and limited variety of chiral monomers, the copolymerization of ACA with achiral monomers for preparing optically active helical polymers is of significant research value.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Emulsion copolymerization of substituted acetylenes for constructing optically active helical polymer nanoparticles. Synergistic effects and helicity inversion

Zhao

Deng

Yang

2016

J. Polym. Sci. Part A: Polym. Chem.

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Copolymerizations of substituted acetylenes have been intensively studied in solution polymerization for constructing chirally helical polymers, while emulsion copolymerizations of the kind of monomers have been only scarcely reported. In the present study, chiral substituted acetylene monomer containing cholic acid group underwent emulsion copolymerizations with an achiral acetylenic monomer in the presence of rhodium catalyst, providing optically active helical copolymer nanoparticles. Synergistic effects were found in the resulting helical copolymers, enabling one certain copolymer to show the maximum CD signal intensity. Moreover, the helicity of the helical copolymers in nanoparticle state was opposite to that in solution state. This is the first demonstration that synergistic effects and helicity inversion simultaneously occurred in helical copolymers prepared by emulsion copolymerization process. To deepen the understanding of the unique phenomena, corresponding solution copolymerization and emulsification process were also investigated. Different from "Sergeant and Soldiers rule" approach, the present study provides a new strategy for preparing chirally helical polymer particles by making full use of achiral monomers.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Emulsion copolymerization of substituted acetylenes for constructing optically active helical polymer nanoparticles. Synergistic effects and helicity inversion

Zhao

Deng

Yang

2016

J. Polym. Sci. Part A: Polym. Chem.

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“…The same group further prepared CPPs with porous structure via precipitation polymerization. [30] As shown in Figure 3, the porous CPPs were prepared in precipitation polymerization using chiral acetylenic monomers derived from cholic acid (ACA) at 0 8C with [Rh(nbd)Cl] 2 as catalyst. For comparison, another acetylenic monomer under-went the same polymerization, but the obtained particles failed to form porous structure.…”

Section: Polymerization Of Chiral Monomersmentioning

confidence: 99%

“…It has proven that the CPPs consisting of chirally helical substituted polyacetylene can be used as chiral seeds for inducing enantioselective crystallization. [8b,27b,67] As a typical example, the porous CPPs prepared by Chen et al [30] were used as additive to induce enantioselective crystallization of racemic BOC-alanine. BOC-L-alanine was preferentially induced, forming rod-like crystals with ee of 69 %.…”

Section: Enantioselective Crystallizationmentioning

confidence: 99%

Preparation and Applications of Chiral Polymeric Particles

Zhang

Huang

Zhao

et al. 2018

Israel Journal of Chemistry

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Chiral polymeric particles (CPPs) have been gathering increasing interest as typical functional polymeric particles in recent decades. This article presents a review on the preparation and applications of CPPs. The methods for preparing CPPs are classified into two major groups: The first one is the direct polymerization of monomers and the other is the post-treatment of preformed polymers. CPPs have been explored as a unique type of chiral materials in various fields like asymmetric catalysis, enantioselective release, enantioselective crystallization, and enantioseparation. This review article is expected to accelerate the progress of scientific research dealing with CPPs and their applications in chirality-related fields.

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“…

enantio-selective crystallization, [12,13] etc. As typical synthetic helical polymers, substituted polyacetylenes have been investigated the most intensively.

…”

mentioning

confidence: 99%

A One‐Pot Polymerization for Concurrently Inducing Predominant Helicity in Optically Inactive Helical Polymer and Constructing Graphene‐Based Chiral Hybrid Foams

Song

et al. 2019

Macromol. Rapid Commun.

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Synthetic chiral helical polymers have achieved impressive progress in past few decades. Unfortunately, how to construct chiral helical polymer‐derived functional materials still remains highly challenging. The present contribution reports an unprecedented, one‐step strategy for judiciously combining chiral helical polymer with graphene to construct chiral hybrid foams. Graphene oxide (GO), ascorbic acid (L‐AA), Rh catalyst, and an achiral acetylenic monomer bearing phenylboronic acid group are mixed in an aqueous dispersion. Under mild conditions, the monomer underwent polymerization; meanwhile GO transforms into reduced graphene oxide (RGO) which in situ self‐assembles to construct a 3D porous structure. Herein, L‐AA simultaneously plays double roles: 1) working as a chiral source for the monomer to undergo helix‐sense‐selective polymerization or transferring its chirality to the polymer chains via forming borate structure; and 2) working as a reducing agent for reducing GO. The preparation strategy combines four processes into one single step: monomer polymerization, chirality transfer, reduction of GO, and RGO's self‐assembly. The eventually obtained chiral hybrid foams demonstrate advantages of porous structure, chirality, and reversible borate functional groups. The established preparation strategy promises a potent platform for conveniently constructing advanced chiral polymeric materials and even chiral hybrids starting from achiral monomers.

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Optically Active Porous Microspheres Consisting of Helical Substituted Polyacetylene Prepared by Precipitation Polymerization without Porogen and the Application in Enantioselective Crystallization

Cited by 18 publications

References 54 publications

Emulsion copolymerization of substituted acetylenes for constructing optically active helical polymer nanoparticles. Synergistic effects and helicity inversion

Emulsion copolymerization of substituted acetylenes for constructing optically active helical polymer nanoparticles. Synergistic effects and helicity inversion

Preparation and Applications of Chiral Polymeric Particles

A One‐Pot Polymerization for Concurrently Inducing Predominant Helicity in Optically Inactive Helical Polymer and Constructing Graphene‐Based Chiral Hybrid Foams

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