High Affinity of Water-Soluble Cryptophanes for Cesium Cations

被引：43

作者：

Brotin, Thierry ^{[1
]}

Montserret, Roland ^{[3
]}

Bouchet, Aude ^{[2
]}

Cavagnat, Dominique ^{[2
]}

Linares, Mathieu ^{[4
]}

Buffeteau, Thierry ^{[2
]}

机构：

[1] Ecole Normale Super Lyon, Lab Chim ENS LYON, UMR CNRS 5182, F-69364 Lyon 07, France

[2] Univ Bordeaux 1, Inst Mol Sci, UMR CNRS 5255, F-33405 Talence, France

[3] Univ Lyon 1, BMSSI, Inst Biol & Chim Prot, UMR CNRS 5086, F-69367 Lyon, France

[4] Royal Inst Technol, Sch Biotechnol, Dept Theoret Chem, S-10691 Stockholm, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 02期

关键词：

VIBRATIONAL CIRCULAR-DICHROISM; ALKALI-METAL; XE-129; NMR; COMPLEXES; XENON; 1,3-ALTERNATE; ENCAPSULATION; C-1-SYMMETRY; RECOGNITION; LIGANDS;

D O I：

10.1021/jo202259r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Exceptionally high affinity for cesium cations was achieved in aqueous solution using two enantiopure cryptophanes. Complexation of cesium was evidenced by Cs-133 NMR spectroscopy and by electronic circular dichroism (ECD). Binding constants as high as 6 X 10(9) M-1 have been measured by isothermal titration calorimetry (ITC). Very strong complexation of rubidium cations (K similar to 10(6) M-1) has also been measured. Chiral hosts allowed the detection of the two cations at low concentrations (mu M) using ECD.

引用

页码：1198 / 1201

页数：4

共 32 条

[1] Closed and Open Clamlike Structures Formed by Hydrogen-Bonded Pairs of Cyclotricatechylene Anions that Contain Cationic "Meat" [J].

Abrahams, Brendan F. ;

FitzGerald, Nicholas J. ;

Hudson, Timothy A. ;

Robson, Richard ;

Waters, Tom .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (17) :3129-3132

[2] Syntheses of diethyleneoxy bridged cryptophanes and their complexing abilities with alkali metal and alkylammonium cations [J].

Akabori, S ;

Miura, M ;

Takeda, M ;

Yuzawa, S ;

Habata, Y ;

Ishii, T .

SUPRAMOLECULAR CHEMISTRY, 1996, 7 (03) :187-193

[3]

Arnaud-Neu F, 2001, CALIXARENES 2001, P642

[4] 129Xe and 1H NMR study of the reversible trapping of xenon by cryptophane-A in organic solution [J].

Bartik, K ;

Luhmer, M ;

Dutasta, JP ;

Collet, A ;

Reisse, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :784-791

[5] Influence of the Chemical Structure of Water-Soluble Cryptophanes on Their Overall Chiroptical and Binding Properties [J].

Bouchet, Aude ;

Brotin, Thierry ;

Linares, Mathieu ;

Cavagnat, Dominique ;

Buffeteau, Thierry .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) :7816-7825

[6] Conformational Effects Induced by Guest Encapsulation in an Enantiopure Water-Soluble Cryptophane [J].

Bouchet, Aude ;

Brotin, Thierry ;

Linares, Mathieu ;

Agren, Hans ;

Cavagnat, Dominique ;

Buffeteau, Thierry .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) :1372-1383

[7] Induced Chiroptical Changes of a Water-Soluble Cryptophane by Encapsulation of Guest Molecules and Counterion Effects [J].

Bouchet, Aude ;

Brotin, Thierry ;

Cavagnat, Dominique ;

Buffeteau, Thierry .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (15) :4507-4518

[8] Crown ethers: The search for selective ion ligating agents [J].

Bradshaw, JS ;

Izatt, RM .

ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (08) :338-345

[9]

Brotin T, 2003, EUR J ORG CHEM, V2003, P973

[10] 129Xe NMR spectroscopy of deuterium-labeled cryptophane-A xenon complexes:: Investigation of host-guest complexation dynamics [J].

Brotin, T ;

Lesage, A ;

Emsley, L ;

Collet, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) :1171-1174

← 1 2 3 4 →