Crown-6-calix[4]arene-capped calix[4]pyrrole: An ion-pair receptor for solvent-separated CsF ions

被引：147

作者：

Sessler, Jonathan L. ^{[1
]}

Kim, Sung Kuk ^{[1
]}

Gross, Dustin E. ^{[1
]}

Lee, Chang-Hee ^{[2
]}

Kim, Jong Seung ^{[3
]}

Lynch, Vincent M. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

[2] Kangwon Natl Univ, Dept Chem, Chunchon 200701, South Korea

[3] Korea Univ, Dept Chem, Seoul 136701, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 39期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1021/ja804976f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An ion-pair receptor, 1, containing both cation- and anion-recognizing sites, has been synthesized and characterized. Single-crystal X-ray diffraction structural studies and H-1 NMR spectroscopic analyses confirmed that 1 forms stable 1:1 complexes with CsF in solution and in the solid state in spite of the large separation enforced between the receptor-bound anion and cation. In 9:1 CDCl3/CD3OD, binding of fluoride anion within the calix[4]pyrrole core of 1 was not observed in the absence of a cobound cesium cation; however, it was seen in this solvent mixture under conditions where a Cs+ cation was bound to the crown ether-strapped calix[4]arene subunit.

引用

页码：13162 / 13166

页数：5

共 40 条

[1]

Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO

[2]

2-G

[3] Facilitated transport of hydrophilic salts by mixtures of anion and cation carriers and by ditopic carriers [J].

Chrisstoffels, LAJ ;

de Jong, F ;

Reinhoudt, DN ;

Sivelli, S ;

Gazzola, L ;

Casnati, A ;

Ungaro, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10142-10151

[4] Calix[4]pyrrole: An old yet new ion-pair receptor [J].

Custelcean, R ;

Delmau, LH ;

Moyer, BA ;

Sessler, JL ;

Cho, WS ;

Gross, D ;

Bates, GW ;

Brooks, SJ ;

Light, ME ;

Gale, PA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (17) :2537-2542

[5] Development of synthetic membrane transporters for anions [J].

Davis, Anthony P. ;

Sheppard, David N. ;

Smith, Bradley D. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) :348-357

[6] A macrobicyclic receptor with versatile recognition properties: Simultaneous binding of an ion pair and selective complexation of dimethylsulfoxide [J].

Deetz, MJ ;

Shang, M ;

Smith, BD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) :6201-6207

[7] Calixpyrroles [J].

Gale, PA ;

Sessler, JL ;

Král, V .

CHEMICAL COMMUNICATIONS, 1998, (01) :1-8

[8] Calix[4]pyrroles: Old yet new anion-binding agents [J].

Gale, PA ;

Sessler, JL ;

Kral, V ;

Lynch, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5140-5141

[9] Anion and ion-pair receptor chemistry: highlights from 2000 and 2001 [J].

Gale, PA .

COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :191-221

[10] Crown ethers: Sensors for ions and molecular scaffolds for materials and biological models [J].

Gokel, GW ;

Leevy, WM ;

Weber, ME .

CHEMICAL REVIEWS, 2004, 104 (05) :2723-2750

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