Helix-Sense-Selective Radical Polymerization of N-(Triphenylmethyl)methacrylamides and Properties of the Polymers

被引：0
|
作者：
Naohiro Hoshikawa
Chiyo Yamamoto
Yuji Hotta
Yoshio Okamoto
机构：
[1] Graduate School of Engineering,Department of Applied Chemistry
[2] Nagoya University,undefined
[3] EcoTopia Science Institute,undefined
[4] Nagoya University,undefined
来源：
Polymer Journal | 2006年 / 38卷
关键词：
Methacrylamide; Helicity; Optically Active Polymer; Chiral Recognition; Isotactic Polymer;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
N-(Triphenylmethyl)methacrylamide (TrMAM) and N-[di(4-butylphenyl)-phenylmethyl]methacrylamide (DBuTrMAM) were polymerized using a radical initiator. The obtained poly(TrMAM) was insoluble in common organic solvents, but poly(DBuTrMAM) was soluble in chloroform and THF. Both polymers were dissolved in conc. H2SO4 accompanied by cleavage of the side groups to give poly(methacrylamide) (poly(MAM)). The 1H NMR of the polymers in D2SO4 indicated that the polymers obtained at low temperature were nearly 100% isotactic. The poly(MAM) with almost 100% isotacticity showed a crystallinity. The poly(DBuTrMAM) formed a lyotropic crystalline phase in chloroform. The radical polymerization of the monomers in the presence of various chiral additives produced optically active polymers having a prevailing helicity. The optically active poly(TrMAM) exhibited a low chiral recognition.
引用
收藏
页码：1258 / 1266
页数：8
相关论文
共 50 条
  • [41] Helix-sense-selective radical polymerization of (S)-6-acryloyl-2,2'-bisalkoxy-1,1'-binaphthyl
    Chen, Yehui
    Yang, Liwen
    Yang, Nianfa
    Yan, Jingyi
    Yang, Zhusheng
    POLYMER BULLETIN, 2015, 72 (12) : 3183 - 3190
  • [42] Assignment of helical sense for poly(phenylacetylene) bearing achiral galvinoxyl chromophore synthesized by helix-sense-selective polymerization
    Kaneko, T
    Umeda, Y
    Yamamoto, T
    Teraguchi, M
    Aoki, T
    MACROMOLECULES, 2005, 38 (23) : 9420 - 9426
  • [43] Helix-sense-selective anionic polymerization of a bulky methacrylamide using organozincates having sugar Residues
    Tsuji, Masashi
    Azam, A. K. M. Fakhrul
    Kamigaito, Masami
    Okamoto, Yoshio
    MACROMOLECULES, 2007, 40 (10) : 3518 - 3520
  • [44] HELIX-SENSE-SELECTIVE POLYMERIZATION OF DIPHENYL-2-PYRIDYLMETHYL METHACRYLATE WITH CHIRAL ANIONIC INITIATORS
    OKAMOTO, Y
    MOHRI, H
    NAKANO, T
    HATADA, K
    CHIRALITY, 1991, 3 (04) : 277 - 284
  • [45] Role of chiral amine cocatalysts in the helix-sense-selective polymerization of a phenylacetylene using a catalytic system
    Sato, T
    Aoki, T
    Teraguchi, M
    Kaneko, T
    Kim, SY
    POLYMER, 2004, 45 (24) : 8109 - 8114
  • [46] RADICAL POLYMERIZATION OF N-SUBSTITUTED METHACRYLAMIDES
    ULBRICH, K
    KOPECEK, J
    EUROPEAN POLYMER JOURNAL, 1976, 12 (03) : 183 - 187
  • [47] Fast Living Polymerization and Helix-Sense-Selective Polymerization of Diazoacetates Using Air-Stable Palladium(II) Catalysts
    Wu, Zong-Quan (zqwu@hfut.edu.cn), 1600, American Chemical Society (140):
  • [48] Helix-Sense-Selective Polymerization of 3,5-bis(hydroxymethyl)phenylacetylene Rigidly Bearing Galvinoxyl Residues and Their Chiroptical Properties
    Shi, Zhichun
    Wang, Jianjun
    Teraguchi, Masahiro
    Aoki, Toshiki
    Kaneko, Takashi
    POLYMERS, 2019, 11 (11)
  • [49] Helix-sense-selective polymerization of phenylacetylene having two hydroxy groups using a chiral catalytic system
    Aoki, T
    Kaneko, T
    Maruyama, N
    Sumi, A
    Takahashi, M
    Sato, T
    Teraguchi, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) : 6346 - 6347
  • [50] Pseudo helix-sense-selective polymerisation of achiral substituted acetylenes
    Zang, Yu
    Aoki, Toshiki
    Liu, Lijia
    Abe, Yunosuke
    Kakihana, Yuriko
    Teraguchi, Masahiro
    Kaneko, Takashi
    CHEMICAL COMMUNICATIONS, 2012, 48 (39) : 4761 - 4763
12345