Synthesis and macromolecular helicity induction of a stereoregular polyacetylene bearing a carboxy group with natural amino acids in water

被引:117
作者
Saito, MA
Maeda, K
Onouchi, H
Yashima, E [1 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Nagoya, Aichi 4648603, Japan
[2] JST, PRESTO, Nagoya, Aichi 4648603, Japan
关键词
D O I
10.1021/ma000484j
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A study is carried out to demonstrate that a stereoregular, cis-transoidal poly(4-carboxyphenyl)acatylene (poly-1-H) can be prepared directly by the homogeneous, stereospecific polymerization of (4-carboxyphenyl)acetylene (1-H) in water in the absence of surfactants and any organic solvents, using water-soluble rhodium complexes in the presence of bases. Furthermore, it is shown that the macromolecular helicity can be induced on the polymer in water as a result of noncovalent, electrostatic interactions with natural, free amino acids.
引用
收藏
页码:4616 / 4618
页数:3
相关论文
共 58 条
[51]   Coordination and coupling of OH-functionalized C-2 units at a single metal center: The synthesis of alkynyl(vinylidene), alkynyl(enyne), bis(alkynyl)hydrido, enynyl, and hexapentaene rhodium complexes from propargylic alcohols as precursors [J].
Werner, H ;
Wiedemann, R ;
Mahr, N ;
Steinert, P ;
Wolf, J .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (05) :561-569
[52]   DNA-LIKE DOUBLE HELIX FORMED BY PEPTIDE NUCLEIC-ACID [J].
WITTUNG, P ;
NIELSEN, PE ;
BUCHARDT, O ;
EGHOLM, M ;
NORDEN, B .
NATURE, 1994, 368 (6471) :561-563
[53]   POLY((4-CARBOXYPHENYL)ACETYLENE) AS A PROBE FOR CHIRALITY ASSIGNMENT OF AMINES BY CIRCULAR-DICHROISM [J].
YASHIMA, E ;
MATSUSHIMA, T ;
OKAMOTO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (46) :11596-11597
[54]   Chirality assignment of amines and amino alcohols based on circular dichroism induced by helix formation of a stereoregular poly((4-carboxyphenyl)acetylene) through acid-base complexation [J].
Yashima, E ;
Matsushima, T ;
Okamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) :6345-6359
[55]   Memory of macromolecular helicity assisted by interaction with achiral small molecules [J].
Yashima, E ;
Maeda, K ;
Okamoto, Y .
NATURE, 1999, 399 (6735) :449-451
[56]   Absolute configurations of N,N-dialkyl α-amino acids and β-amino alcohols from exciton-coupled circular dichroism spectra of Cu(II) complexes [J].
Zahn, S ;
Canary, JW .
ORGANIC LETTERS, 1999, 1 (06) :861-864
[57]   CHIRAL DISCRIMINATION IN THE STRUCTURES AND ENERGETICS OF ASSOCIATION OF STEREOISOMERIC SALTS OF MANDELIC-ACID WITH ALPHA-PHENETHYLAMINE, EPHEDRINE, AND PSEUDOEPHEDRINE [J].
ZINGG, SP ;
ARNETT, EM ;
MCPHAIL, AT ;
BOTHNERBY, AA ;
GILKERSON, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1565-1580
[58]  
1988, MOL CONFORMATION DYN, P53403