Helix-sense-selective polymerization of phenylacetylene having two hydroxy groups using a chiral catalytic system

被引:295
作者
Aoki, T [1 ]
Kaneko, T [1 ]
Maruyama, N [1 ]
Sumi, A [1 ]
Takahashi, M [1 ]
Sato, T [1 ]
Teraguchi, M [1 ]
机构
[1] Niigata Univ, Fac Engn, Dept Chem & Chem Engn, Niigata 9502181, Japan
关键词
D O I
10.1021/ja021233o
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have found a simple and novel synthetic method for obtaining a chiral polymer from an achiral monomer by using a chiral catalytic system. The chirality of the polymer was caused only by a one-handed helical backbone, and the polymer had no other chiral structures in the side groups. In addition, the helical conformation was stable in solution by itself. This is the first example of helix-sense-selective polymerization of a substituted acetylene. The stability of the helicity was found to be caused by intramolecular hydrogen bonds. Copyright © 2003 American Chemical Society.
引用
收藏
页码:6346 / 6347
页数:2
相关论文
共 27 条
[1]   Helical polyacetylene synthesized with a chiral nematic reaction field [J].
Akagi, K ;
Piao, G ;
Kaneko, S ;
Sakamaki, K ;
Shirakawa, H ;
Kyotani, M .
SCIENCE, 1998, 282 (5394) :1683-1686
[2]   CHIRAL HELICAL CONFORMATION OF THE POLYPHENYLACETYLENE HAVING OPTICALLY-ACTIVE BULKY SUBSTITUENT [J].
AOKI, T ;
KOKAI, M ;
SHINOHARA, K ;
OIKAWA, E .
CHEMISTRY LETTERS, 1993, (12) :2009-2012
[3]   Synthesis and properties of polymers from disubstituted acetylenes with chiral pinanyl groups [J].
Aoki, T ;
Kobayashi, Y ;
Kaneko, T ;
Oikawa, E ;
Yamamura, Y ;
Fujita, Y ;
Teraguchi, M ;
Nomura, R ;
Masuda, T .
MACROMOLECULES, 1999, 32 (01) :79-85
[4]   Supramolecular polymers [J].
Brunsveld, L ;
Folmer, BJB ;
Meijer, EW ;
Sijbesma, RP .
CHEMICAL REVIEWS, 2001, 101 (12) :4071-4097
[5]   ENANTIOSELECTIVE POLYMERIZATIONS OF ACHIRAL ISOCYANIDES - PREPARATION OF OPTICALLY-ACTIVE HELICAL POLYMERS USING CHIRAL NICKEL-CATALYSTS [J].
DEMING, TJ ;
NOVAK, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7926-7927
[6]   IDEAL EXCITON SPECTRA IN SINGLE-SCREW AND DOUBLE-SCREW SENSE HELICAL POLYSILANES [J].
FUJIKI, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6017-6018
[7]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180
[8]  
Green MM, 1999, ANGEW CHEM INT EDIT, V38, P3139
[9]   Highly screw-sense selective polymerization of 1,2-diisocyano-3,6-di-p-tolylbenzene initiated by optically active binaphthylpalladium(II) complexes [J].
Ito, Y ;
Ohara, T ;
Shima, R ;
Suginome, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9188-9189
[10]   SCREW SENSE SELECTIVE POLYMERIZATION OF ACHIRAL ISOCYANIDES CATALYZED BY OPTICALLY-ACTIVE NICKEL(II) COMPLEXES [J].
KAMER, PCJ ;
NOLTE, RJM ;
DRENTH, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6818-6825