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通过苯乙炔的活性聚合合成由螺旋状聚（苯乙炔）链组成的光学活性星形聚合物及其手性光学性质。

Synthesis of optically active star polymers consisting of helical poly(phenylacetylene) chains by the living polymerization of phenylacetylenes and their chiroptical properties.

作者信息

Inaba Ayato, Nishimura Tatsuya, Yamamoto Masato, Das Sandip, Yurtsever Ayhan, Miyata Kazuki, Fukuma Takeshi, Kawaguchi Seigo, Kikuchi Moriya, Taniguchi Tsuyoshi, Maeda Katsuhiro

机构信息

Graduate School of Natural Science and Technology, Kanazawa University Kakuma-machi Kanazawa 920-1192 Japan

Nano Life Science Institute (WPI-NanoLSI), Kanazawa University Kakuma-machi Kanazawa 920-1192 Japan.

出版信息

RSC Adv. 2023 Oct 23;13(44):30978-30984. doi: 10.1039/d3ra05971e. eCollection 2023 Oct 18.

DOI:10.1039/d3ra05971e
PMID:37876657
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10591293/
Abstract

Star polymers consisting of three helical poly(phenylacetylene) chains with a precisely controlled molecular weight (molar mass dispersity < 1.03) were successfully synthesized by the living polymerization of phenylacetylene derivatives with a Rh-based multicomponent catalyst system comprising trifunctional initiators, which have three phenylboronates centered on a benzene ring, the Rh complex [Rh(nbd)Cl], diphenylacetylene, triphenylphosphine, and a base. The analysis of chiroptical properties of the optically active star polymers obtained by the living polymerization of optically active phenylacetylene derivatives revealed that the star polymers exhibited chiral amplification properties owing to their unique topology compared with the corresponding linear polymers.

摘要

通过苯乙炔衍生物与基于铑的多组分催化剂体系进行活性聚合，成功合成了由三条具有精确控制分子量（摩尔质量分散度<1.03）的螺旋状聚（苯乙炔）链组成的星形聚合物。该催化剂体系包括三官能引发剂，其具有以苯环为中心的三个苯基硼酸酯、铑配合物[Rh(nbd)Cl]、二苯乙炔、三苯基膦和一种碱。对通过光学活性苯乙炔衍生物的活性聚合得到的光学活性星形聚合物的手性光学性质分析表明，与相应的线性聚合物相比，星形聚合物由于其独特的拓扑结构而表现出手性放大性质。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/6f9e76d39047/d3ra05971e-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/66fe6f331fe6/d3ra05971e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/0631ba376d13/d3ra05971e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/71d5734a9335/d3ra05971e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/abcfcff31dcf/d3ra05971e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/65c17fbd9dff/d3ra05971e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/5bbd7ffbf8a6/d3ra05971e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/6f520039f34c/d3ra05971e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/5eadb375d241/d3ra05971e-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/0c73889d6418/d3ra05971e-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/6f9e76d39047/d3ra05971e-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/66fe6f331fe6/d3ra05971e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/0631ba376d13/d3ra05971e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/71d5734a9335/d3ra05971e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/abcfcff31dcf/d3ra05971e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/65c17fbd9dff/d3ra05971e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/5bbd7ffbf8a6/d3ra05971e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/6f520039f34c/d3ra05971e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/5eadb375d241/d3ra05971e-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/0c73889d6418/d3ra05971e-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2df/10591293/6f9e76d39047/d3ra05971e-f6.jpg

相似文献

[1]
Synthesis of optically active star polymers consisting of helical poly(phenylacetylene) chains by the living polymerization of phenylacetylenes and their chiroptical properties.

RSC Adv. 2023-10-23

[2]
Well-Controlled Living Polymerization of Phenylacetylenes in Water: Synthesis of Water-Soluble Stereoregular Telechelic Poly(phenylacetylene)s.

Angew Chem Int Ed Engl. 2022-6-27

[3]
Facile and Versatile Synthesis of End-Functionalized Poly(phenylacetylene)s: A Multicomponent Catalytic System for Well-Controlled Living Polymerization of Phenylacetylenes.

Angew Chem Int Ed Engl. 2020-3-19

[4]
Alkyne-Palladium(II)-Catalyzed Living Polymerization of Isocyanides: An Exploration of Diverse Structures and Functions.

Acc Chem Res. 2021-10-19

[5]
[Rh(L-alaninate)(1,5-Cyclooctadiene)] Catalyzed Helix-Sense-Selective Polymerizations of Achiral Phenylacetylenes.

Polymers (Basel). 2018-11-3

[6]
Helix-Sense-Selective Polymerization of 3,5-bis(hydroxymethyl)phenylacetylene Rigidly Bearing Galvinoxyl Residues and Their Chiroptical Properties.

Polymers (Basel). 2019-11-13

[7]
Helix-Sense-Selective Polymerization of Achiral Phenylacetylenes with Two -Alkylamide Groups to Generate the One-Handed Helical Polymers Stabilized by Intramolecular Hydrogen Bonds.

ACS Macro Lett. 2012-11-20

[8]
Temperature dependence of helical structures of poly(phenylacetylene) derivatives bearing an optically active substituent.

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[9]
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[10]
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本文引用的文献

[1]
Well-Controlled Living Polymerization of Phenylacetylenes in Water: Synthesis of Water-Soluble Stereoregular Telechelic Poly(phenylacetylene)s.

Angew Chem Int Ed Engl. 2022-6-27

[2]
Alkyne-Palladium(II)-Catalyzed Living Polymerization of Isocyanides: An Exploration of Diverse Structures and Functions.

Acc Chem Res. 2021-10-19

[3]
Rhodium(I) Complexes Bearing an Aryl-Substituted 1,3,5-Hexatriene Chain: Catalysts for Living Polymerization of Phenylacetylene and Potential Helical Chirality of 1,3,5-Hexatrienes.

Angew Chem Int Ed Engl. 2021-10-4

[4]
Synthesis of Stereoregular Telechelic Poly(phenylacetylene)s: Facile Terminal Chain-End Functionalization of Poly(phenylacetylene)s by Terminative Coupling with Acrylates and Acrylamides in Rhodium-Catalyzed Living Polymerization of Phenylacetylenes.

J Am Chem Soc. 2021-3-10

[5]
Facile and Versatile Synthesis of End-Functionalized Poly(phenylacetylene)s: A Multicomponent Catalytic System for Well-Controlled Living Polymerization of Phenylacetylenes.

Angew Chem Int Ed Engl. 2020-3-19

[6]
Structure-property relationship of a model network containing solvent.

Sci Technol Adv Mater. 2019-6-11

[7]
Nano-Star-Shaped Polymers for Drug Delivery Applications.

Macromol Rapid Commun. 2017-9-12

[8]
Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions.

Chem Rev. 2016-10-18

[9]
Star Polymers.

Chem Rev. 2016-6-14

[10]
Chirality induction using circularly polarized light into a branched oligofluorene derivative in the presence of an achiral aid molecule.

Chem Commun (Camb). 2016-1-31

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