Selective Synthesis of Single-Handed Helical Polymers from Achiral Monomer and a Mechanism Study on Helix-Sense-Selective Polymerization

被引：54
|
作者：
Zhou, Li [1 ,2 ]
Xu, Xun-Hui [1 ,2 ]
Jiang, Zhi-Qiang [1 ,2 ]
Xu, Lei [1 ,2 ]
Chu, Ben-Fa [1 ,2 ]
Liu, Na [1 ,2 ]
Wu, Zong-Quan [1 ,2 ]
机构：
[1] Hefei Univ Technol, Sch Chem & Chem Engn, Dept Polymer Sci & Engn, 193 Tunxi Rd, Hefei 230009, Anhui, Peoples R China
[2] Hefei Univ Technol, Anhui Key Lab Catalyt Mat & React Engn, 193 Tunxi Rd, Hefei 230009, Anhui, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 02期
基金：
美国国家科学基金会;
关键词：
chiral polymers; helix; helix-sense-selective polymerization; living polymerization; polymers; CIRCULARLY-POLARIZED LIGHT; BULKY ARYL ISOCYANIDE; SCREW-SENSE; ASYMMETRIC POLYMERIZATION; LIVING POLYMERIZATION; MEDIATED POLYMERIZATION; BLOCK COPOLYMERIZATION; CHIRAL AMPLIFICATION; FACILE SYNTHESIS; MAIN-CHAIN;
D O I：
10.1002/anie.202011661
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Inspired by the exquisite helices in Nature, fabrication of helical materials with controlled handedness has attracted considerable attention. Herein, we report on precis synthesis of single left- and right-handed helical polyisocyanides through living polymerization of achiral monomers using chiral palladium catalysts under helix-sense-selective manner. Mechanism study revealed that the yielded helices with opposite handedness showed different activity of the living chain end. The helix with unfavored handedness was self-terminated, while the one with favored handedness showed high activity and could undergo chain propagation to form a high molecular weight polymer with maintained single-handed helicity.
引用
收藏
页码：806 / 812
页数：7
相关论文
共 50 条
  • [31] Catalytic helix-sense-selective polymerisation of achiral substituted acetylenes containing bulky π-conjugated planar substituents yielding soluble and statically stable one-handed helical polymers
    Zang, Y.
    Wang, X.
    Zhang, W.
    Aoki, T.
    Teraguchi, M.
    Kaneko, T.
    Ma, L.
    Jia, H.
    RSC ADVANCES, 2015, 5 (129) : 106819 - 106823
  • [32] Helix-Sense-Selective Polymerization of Phenylacetylenes Having a Porphyrin and a Zinc-Porphyrin Group: One-Handed Helical Arrangement of Porphyrin Pendants
    Teraguchi, Masahiro
    Nahata, Nobuyuki
    Nishimura, Takahiro
    Aoki, Toshiki
    Kaneko, Takashi
    POLYMERS, 2019, 11 (02)
  • [33] HELIX-SENSE-SELECTIVE POLYMERIZATION OF BULKY METHACRYLATES WITH RADICAL AND ANIONIC INITIATORS
    OKAMOTO, Y
    NAKANO, T
    SHIKISAI, Y
    MATSUDA, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 476 - POLY
  • [34] Helix-Sense-Selective Synthesis of Right- and Left-Handed Helical Luminescent Poly(diphenylacetylene)s with Memory of the Macromolecular Helicity and Their Helical Structures
    Maeda, Katsuhiro
    Nozaki, Mai
    Hashimoto, Kengo
    Shimomura, Kouhei
    Hirose, Daisuke
    Nishimura, Tatsuya
    Watanabe, Go
    Yashima, Eiji
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (16) : 7668 - 7682
  • [35] HELIX-SENSE-SELECTIVE POLYMERIZATION OF 1-PHENYLDIBENZOSUBERYL METHACRYLATE BY FREE-RADICAL MECHANISM
    NAKANO, T
    SHIKISAI, Y
    OKAMOTO, Y
    PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 1995, 71 (08): : 251 - 255
  • [36] Helix-sense selective polymerization of carbodiimides: Building permanently optically active polymers from achiral monomers
    Tian, GL
    Lu, YJ
    Novak, BM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) : 4082 - 4083
  • [37] Helix-Sense-Selective and Enantiomer-Selective Living Polymerization of Phenyl Isocyanide Induced by Reusable Chiral Lactide Using Achiral Palladium Initiator
    Chen, Jia-Li
    Yang, Li
    Wang, Qian
    Jiang, Zhi-Qiang
    Liu, Na
    Yin, Jun
    Ding, Yunsheng
    Wu, Zong-Quan
    MACROMOLECULES, 2015, 48 (21) : 7737 - 7746
  • [38] Helix-Sense Selective Polymerization of Carbodiimides: Building Permanently Optically Active Polymers from Achiral Monomers
    1600, American Chemical Society (126):
  • [39] Helix Sense-Selective Supramolecular Polymerization Seeded by a One-Handed Helical Polymeric Assembly
    Zhang, Wei
    Jin, Wusong
    Fukushima, Takanori
    Mori, Tadashi
    Aida, Takuzo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (43) : 13792 - 13795
  • [40] Helical polyguanidines prepared by helix-sense-selective polymerizations of achiral carbodiimides using enantiopure binaphthol-based titanium catalysts
    Tang, Hong-Zhi
    Garland, Eva R.
    Novak, Bruce M.
    He, Jiangtao
    Polavarapu, Prasad L.
    Sun, Frank Chen
    Sheiko, Sergei S.
    MACROMOLECULES, 2007, 40 (10) : 3575 - 3580
12345