Molecular Tweezers: Synthesis and Formation of Host-Guest Complexes

被引：27

作者：

Legouin, Beatrice ^{[1
]}

Gayral, Maud ^{[1
]}

Uriac, Philippe ^{[1
]}

Cupif, Jean-Francois ^{[1
]}

Levoin, Nicolas ^{[2
]}

Toupet, Loic ^{[3
]}

van de Weghe, Pierre ^{[1
]}

机构：

[1] Univ Rennes 1, Fac Sci Biol & Pharmaceut, EA Subst Lichen & Photoprotect, F-35043 Rennes, France

[2] Biopiojet Biotech, F-35762 St Gregoire, France

[3] Univ Rennes 1, CNRS, GM CM, UMR 6509, F-35042 Rennes, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 28期

关键词：

Supramolecular chemistry; Host-guest systems; Pi interactions; Molecular recognition; BIOLOGICAL INTEREST; NITRO-DERIVATIVES; RECOGNITION; CONSTANTS; SHIFT;

D O I：

10.1002/ejoc.201000729

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral molecular tweezer obtained from (+)-usnic acid placed in solution in the presence of various aromatic compounds afforded complexes with low association constants. Thus, the X-ray structure of assembly 3i is presented, where the guest is sandwiched between the two pincers of the tweezer. The association constants for various guests were determined through different methods. Finally, other tweezers with electron-rich aromatic aldehydes and ketones were prepared from (1R,2R)-1,2-diaminocyclohexane. The most interesting complexes were also confirmed through structural analysis, and the best results were obtained with 10-hydroxyphenanthrene-9-carbaldehyde (5i) as the aromatic moiety.

引用

页码：5503 / 5508

页数：6

共 25 条

[1] TAUTOMERISM OF REPRESENTATIVE AROMATIC ALPHA-HYDROXY CARBALDEHYDE ANILS AS STUDIED BY SPECTROSCOPIC METHODS AND AM1 CALCULATIONS - SYNTHESIS OF 10-HYDROXYPHENANTHRENE-9-CARBALDEHYDE [J].