Double helix formation of poly(m-phenylene)s bearing achiral oligo(ethylene oxide) pendants and transformation into an excess of one-handed single helix through cholate binding in water

被引：24

作者：

Ben, Teng ^{[1
,2
]}

Furusho, Yoshio ^{[1
,3
]}

Goto, Hidetoshi ^{[1
]}

Miwa, Kazuhiro ^{[3
]}

Yashima, Eiji ^{[1
,3
]}

机构：

[1] Japan Sci & Technol Agcy, Yashima Super Struct Helix Project, Tokyo, Japan

[2] Jilin Univ, Alan G MacDiarmid Inst, Changchun 130012, Peoples R China

[3] Nagoya Univ, Dept Mol Design & Engn, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 12期

基金：

日本学术振兴会; 日本科学技术振兴机构; 中国国家自然科学基金;

关键词：

LINEAR STRUCTURE; AQUEOUS-SOLUTION; SIDE-CHAINS; POLYMERS; OLIGORESORCINOLS; RECOGNITION; CHIRALITY; PNA; SPECTROSCOPY; CHOLESTEROL;

D O I：

10.1039/b903546j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A water-soluble poly(m-phenylene) bearing an achiral oligo(ethylene oxide) chain at the 5-position was synthesized by the Ni(0)-mediated homo-coupling polycondensation of a 3,5-dibromophenol monomer. The poly(m-phenylene) adopted a single helical conformation in protic media and self-assembled into a double helix in water through aromatic interaction, while it took a random-coil conformation in chloroform. Upon the addition of sodium cholate in water, the double helical poly(m-phenylene) was transformed into single strands, which bound the cholate molecules to form an excess of one-handed single helix.

引用

页码：2509 / 2512

页数：4

共 66 条

[41] Solvophobically driven folding of nonbiological oligomers [J].

Nelson, JC ;

Saven, JG ;

Moore, JS ;

Wolynes, PG .

SCIENCE, 1997, 277 (5333) :1793-1796

[42] Peptide nucleic acid. A molecule with two identities [J].

Nielsen, PE .

ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (07) :624-630

[43] Design and synthesis of semiflexible substituted polyacetylenes with helical conformation [J].

Nomura, R ;

Nakako, H ;

Masuda, T .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 190 (1-2) :197-205

[44] A helical polyelectrolyte induced by specific interactions with biomolecules in water [J].

Onouchi, H ;

Maeda, K ;

Yashima, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7441-7442

[45] Control of dynamic helicity at the macro- and supramolecular level [J].

Pijper, Dirk ;

Feringa, Ben L. .

SOFT MATTER, 2008, 4 (07) :1349-1372

[46] Pulsed gradient spin-echo (PGSE) diffusion and 1H,19F heteronuclear overhauser spectroscopy (HOESY) NMR methods in inorganic and organometallic chemistry:: Something old and something new [J].

Pregosin, PS ;

Kumar, PGA ;

Fernández, I .

CHEMICAL REVIEWS, 2005, 105 (08) :2977-2998

[47] Cooperative conformational transitions in phenylene ethynylene oligomers: Chain-length dependence [J].

Prince, RB ;

Saven, JG ;

Wolynes, PG ;

Moore, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3114-3121

[48]

Prince RB, 2000, ANGEW CHEM INT EDIT, V39, P228, DOI 10.1002/(SICI)1521-3773(20000103)39:1<228::AID-ANIE228>3.0.CO

[49]

2-B

[50] Foldamer-based molecular recognition [J].

Prince, RB ;

Barnes, SA ;

Moore, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2758-2762

← 1 2 3 4 5 6 7 →