Bis(imidazolium)-Calix[4]arene Receptors for Anion Binding

被引：44

作者：

Dinares, Immaculada ^{[1
]}

de Miguel, Cristina Garcia ^{[1
]}

Mesquida, Neus ^{[1
]}

Alcalde, Ermitas ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 01期

关键词：

IMIDAZOLIUM RECEPTORS; N-ARYLATION; RECOGNITION; COMPLEXATION; COORDINATION; FRAMEWORKS; SOLVENT; LIGAND;

D O I：

10.1021/jo8023285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient access to the bis(imidazolyl)calixarene 2 and dicationic bis(imidazolium) salts la,b center dot 2X directly bonded to the upper rim of calixarene structure has been reported. Anion binding properties of the new receptors were Studied by H-1 NMR spectroscopic methods. Bis(N-butylimidazolium) dication la exhibited the best recognition properties toward carboxylate anions with a 1:1 receptor-anion binding stoichiometry, whereas the presence of a bulky group such as isopropyl (1b) increased the difficulty of both imidazolium moieties to be able to support the association with the same single anion.

引用

页码：482 / 485

页数：4

共 37 条

[1] Synthetic approaches to sterically hindered N-arylimidazoles through copper-catalyzed coupling reactions [J].

Alcalde, E ;

Dinarès, I ;

Rodríguez, S ;

de Miguel, CG .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1637-1643

[2] Hydrogen bonded driven anion binding by dicationic [14]imidazoliophanes [J].

Alcalde, E ;

Alvarez-Rúa, C ;

García-Granda, S ;

García-Rodriguez, E ;

Mesquida, N ;

Pérez-García, L .

CHEMICAL COMMUNICATIONS, 1999, (03) :295-296

[3] Imidazolium-based dicationic cyclophanes.: Solid-state aggregates with unconventional (C-H)+•••Cl- hydrogen bonding revealed by X-ray diffraction [J].

Alcalde, Ermitas ;

Mesquida, Neus ;

Vilaseca, Marta ;

Alvarez-Rua, Carmen ;

Garcia-Granda, Santiago .

SUPRAMOLECULAR CHEMISTRY, 2007, 19 (07) :501-509

[4] Imidazolium-based [14]heterophanes as models for anion recognition [J].

Alcalde, Ermitas ;

Mesquida, Neus ;

Perez-Garcia, Lluisa .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (17) :3988-3996

[5] Copper-catalyzed N-arylation of imidazoles and benzimidazoles [J].

Altman, Ryan A. ;

Koval, Erica D. ;

Buchwald, Stephen L. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6190-6199

[6] Calixarene-based multivalent ligands [J].

Baldini, L. ;

Casnati, A. ;

Sansone, F. ;

Ungaro, R. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) :254-266

[7] Molecular recognition of oxoanions based on guanidinium receptors [J].

Blondeau, Pascal ;

Segura, Margarita ;

Perez-Fernandez, Ruth ;

de Mendoza, Javier .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) :198-210

[8] Novel chiral calix[4]arenes by direct asymmetric epoxidation reaction [J].

Bonini, Carlo ;

Chiummiento, Lucia ;

Funicello, Maria ;

Lopardo, Maria Teresa ;

Lupattelli, Paolo ;

Laurita, Alessandro ;

Cornia, Andrea .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (11) :4233-4236

[9] Buried solvent determines both anion-binding selectivity and binding stoichiometry with hydrogen-bonding receptors [J].

Burns, DH ;

Calderon-Kawasaki, K ;

Kularatne, S .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2803-2807

[10] Bis(amido)calix[4]arenes in the pinched cone conformation as tuneable hydrogen-bonding anion receptors [J].

Cameron, BR ;

Loeb, SJ .

CHEMICAL COMMUNICATIONS, 1997, (06) :573-574

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