Chiral recognition in noncovalent bonding interactions between helicenes: right-handed helix favors right-handed helix over left-handed helix

被引：103

作者：

Amemiya, Ryo ^{[1
]}

Yamaguchi, Masahiko ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 980, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 01期

关键词：

D O I：

10.1039/b713700a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Our studies of helicenes are summarized in regard to chiral recognition phenomenon in noncovalent bonding interactions. The interactions between helical molecules show a tendency for pairs of the same configuration of the helicenes to form more stable complexes than pairs of enantiomeric helicenes. The observations are made in charge transfer complexation, crystallization, homocoupling reaction, layer structure formation, self-aggregation, and double helix formation. The interactions between a helicene and a right-handed helical polymer, double strand DNA, are also described.

引用

页码：26 / 35

页数：10

共 139 条

[1]

ABED RE, 2007, TETRAHEDRON LETT, V692, P1156

[2] HELICALLY CHIRAL THIA-QUINQUEPHENYLOPHANES AND DISELENA-QUINQUEPHENYLOPHANES [J].

AIROLA, K ;

BARTRAM, S ;

RISSANEN, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (07) :895-899

[3] Long-range effects of chirality in aromatic poly(isocyanide)s [J].

Amabilino, DB ;

Serrano, JL ;

Sierra, T ;

Veciana, J .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (10) :3161-3174

[4] DIASTEREOISOMERIC CHARGE-TRANSFER COMPLEXES - MEASUREMENT OF THERMODYNAMIC CONSTANTS BY H-1 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].

BALAN, A ;

GOTTLIEB, HE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (02) :350-352

[5] Dynamic chemical devices: Generation of reversible extension/contraction molecular motion by ion-triggered single/double helix interconversion [J].

Barboiu, M ;

Vaughan, G ;

Kyritsakas, N ;

Lehn, JM .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (03) :763-769

[6] TRIS(PHENANTHROLINE)RUTHENIUM(II) - STEREOSELECTIVITY IN BINDING TO DNA [J].

BARTON, JK ;

DANISHEFSKY, AT ;

GOLDBERG, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (07) :2172-2176

[7] SELF-ASSEMBLY OF A DOUBLE-HELICAL COMPLEX OF SODIUM [J].

BELL, TW ;

JOUSSELIN, H .

NATURE, 1994, 367 (6462) :441-444

[8]

Berl V, 2001, CHEM-EUR J, V7, P2810, DOI 10.1002/1521-3765(20010702)7:13<2810::AID-CHEM2810>3.0.CO

[9]

2-5

[10] Interconversion of single and double helices formed from synthetic molecular strands [J].

Berl, V ;

Huc, I ;

Khoury, RG ;

Krische, MJ ;

Lehn, JM .

NATURE, 2000, 407 (6805) :720-723

← 1 2 3 4 5 6 7 8 9 10 →