Guest encapsulation in a water-soluble molecular capsule based on ionic interactions

被引:147
作者
Corbellini, F
Di Costanzo, L
Crego-Calama, M
Geremia, S
Reinhoudt, DN
机构
[1] Univ Twente, Res Inst, Lab Supremol Chem & Technol, NL-7500 AE Enschede, Netherlands
[2] Univ Trieste, Dipartimento Sci Chim, Ctr Eccellenza Biocristallog, I-34127 Trieste, Italy
关键词
D O I
10.1021/ja034535e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report on the synthesis and characterization of a water-soluble molecular capsule based on multiple ionic interactions. The assembly has been studied by means of 1H NMR, ESI-MS spectroscopy, and isothermal titration calorimetry (ITC), showing an association constant in water, Ka, of 3.3 × 104 M-1. The achieved water solubility of the system opens the possibility of using this supramolecular assembly for molecular recognition in pure water. Encapsulation studies have been performed and are reported in this Communication. Copyright © 2003 American Chemical Society.
引用
收藏
页码:9946 / 9947
页数:2
相关论文
共 27 条
[1]   Hydrogen-bonded molecular capsules are stable in polar media [J].
Atwood, JL ;
Barbour, LJ ;
Jerga, A .
CHEMICAL COMMUNICATIONS, 2001, (22) :2376-2377
[2]   Molecular recognition in methanol: The first example of hydrogen-bond-mediated self-association of a calix[4]arene in polar, protic solvent [J].
Brewster, RE ;
Shuker, SB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7902-7903
[3]   Self-assembling capsules [J].
Conn, MM ;
Rebek, J .
CHEMICAL REVIEWS, 1997, 97 (05) :1647-1668
[4]   Guest encapsulation and self-assembly of molecular capsules in polar solvents via multiple ionic interactions [J].
Corbellini, F ;
Fiammengo, R ;
Timmerman, P ;
Crego-Calama, M ;
Versluis, K ;
Heck, AJR ;
Luyten, I ;
Reinhoudt, DN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6569-6575
[5]  
Di Costanzo L, 2001, ANGEW CHEM INT EDIT, V40, P4245, DOI 10.1002/1521-3773(20011119)40:22<4245::AID-ANIE4245>3.0.CO
[6]  
2-#
[7]   Highly stable cage-like complexes by self-assembly of tetracationic Zn(II) porphyrinates and tetrasulfonatocalix[4]arenes in polar solvents [J].
Fiammengo, R ;
Timmerman, P ;
de Jong, F ;
Reinhoudt, DN .
CHEMICAL COMMUNICATIONS, 2000, (23) :2313-2314
[8]   Metal-assembled cobalt(II) resorc[4]arene-based cage molecules that reversibly capture organic molecules from water and act as NMR shift reagents [J].
Fox, OD ;
Leung, JFY ;
Hunter, JM ;
Dalley, NK ;
Harrison, RG .
INORGANIC CHEMISTRY, 2000, 39 (04) :783-790
[9]   A metal-assembled, pH-dependent, resorcinarene-based cage molecule [J].
Fox, OD ;
Dalley, NK ;
Harrison, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (28) :7111-7112
[10]   Molecular paneling via coordination [J].
Fujita, M ;
Umemoto, K ;
Yoshizawa, M ;
Fujita, N ;
Kusukawa, T ;
Biradha, K .
CHEMICAL COMMUNICATIONS, 2001, (06) :509-518