Self-assembly via ionic interactions of calix[6]arene-based receptors displaying remarkable host-guest properties toward neutral guests

被引：29

作者：

Le Gac, Stephane ^{[2
]}

Luhmer, Michel ^{[3
]}

Reinaud, Olivia ^{[4
]}

Jabin, Ivan ^{[1
]}

机构：

[1] Univ Libre Bruxelles, Serv Chim Organ, B-1050 Brussels, Belgium

[2] Univ Havre, Fac Tech Sci, URCOM, F-76058 Le Havre, France

[3] Univ Libre Bruxelles, Lab Rseonance Magnet Nucl Haute Resolut, B-1050 Brussels, Belgium

[4] Univ Paris, CNRS 8601, Lab Chim Biochim Pharmacol Toxicol, UMR, F-75006 Paris, France

来源：

TETRAHEDRON | 2007年 / 63卷 / 44期

关键词：

D O I：

10.1016/j.tet.2007.06.122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The association of a C-3v-symmetrical calix[6]tris-amine with different concave tris-carboxylic acids of various degrees of flexibility has been explored by H-1 NMR spectroscopy. In all cases, self-assembled structures directed by the selective inclusion of a neutral guest molecule were obtained, the more preorganized being stable in protic solvents. With a rigid C-3-symmetrical cap, chiral guest recognition in the calixarene cavity resulted. A large tris-acidic partner gave a unique molecular ditopic receptor that is able to simultaneously accommodate two neutral molecules in two distinct hydrophobic cavities with different binding processes. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：10721 / 10730

页数：10

共 60 条

[1]

Arduini A, 2000, ANGEW CHEM INT EDIT, V39, P3453, DOI 10.1002/1521-3773(20001002)39:19<3453::AID-ANIE3453>3.0.CO

[2]

2-I

[3] Selective synthesis of two constitutionally isomeric oriented calix[6]arene-based rotaxanes [J].

Arduini, A ;

Ciesa, F ;

Fragassi, M ;

Pochini, A ;

Secchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) :278-281

[4] Self-assembled hydrogen-bonded molecular cages of calix[6]arenetricarboxylic acid derivatives [J].

Arduini, A ;

Domiano, L ;

Ogliosi, L ;

Pochini, A ;

Secchi, A ;

Ungaro, R .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7866-7868

[5]

ARDUINI A, 2002, J SUPRAMOL CHEM, V2, P85, DOI DOI 10.1016/S1472-7862(02)00082-5

[6]

Böhmer V, 2000, CALIXARENES IN ACTION, P203, DOI 10.1142/9781848160354_0009

[7] p-(1H-phenanthro[9,10-d]imidazol-2-yl)-substituted calix[4]arene, a deep cavity for guest inclusion [J].

Botana, E ;

Nättinen, K ;

Prados, P ;

Rissanen, K ;

de Mendoza, J .

ORGANIC LETTERS, 2004, 6 (07) :1091-1094

[8] Charged cyclodextrin derivatives as chiral selectors in capillary electrophoresis [J].

Chankvetadze, B ;

Endresz, G ;

Blaschke, G .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :141-&

[9] FLUORENACENES AND FLUORENAPHENES . INDENOFLUORENE SYNTHESES .13. PHENYL DERIVATIVES OF CIS-FLUORENACENE AND TRANS-FLUORENAPHENE [J].

CHARDONNENS, L ;

CHARDONN.H .

HELVETICA CHIMICA ACTA, 1968, 51 (08) :1998-+

[10] Bridged calix[6]arenes [J].

Chen, YY ;

Gong, SL .

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2003, 45 (3-4) :165-184

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