Sequential formation of a ternary complex among dihexylammonium, cucurbit[6]uril, and cyclodextrin with positive cooperativity.

A unique ternary 1:1:1 cucurbit[6]uril (CB[6])-cyclodextrin (CD)-dihexylammonium (DHA) complex was designed and noncovalently synthesized in stepwise fashion: first, CB[6] interacts strongly with DHA to form a 1:1 complex; second, addition of CD into the solution of the 1:1 complex leads to the exclusive formation of the 1:1:1 ternary complex. The ternary complex was characterized by various experimental techniques including ITC, NMR, and ESI-MS.

[1]  Y. Inoue,et al.  Complexation Thermodynamics of Cyclodextrins. , 1998, Chemical reviews.

[2]  L. Mutihac,et al.  Complex Formation of Crown Ethers with the Cucurbit[6]uril–Spermidine and Cucurbit[6]uril–Spermine Complex in Aqueous Solution , 2005 .

[3]  Lyle Isaacs,et al.  Die Cucurbit[n]uril‐Familie , 2005 .

[4]  Eunsung Lee,et al.  New Cucurbituril Homologues: Syntheses, Isolation, Characterization, and X-ray Crystal Structures of Cucurbit[n]uril (n = 5, 7, and 8) , 2000 .

[5]  Y. Ko,et al.  Inclusion of methylviologen in cucurbit[7]uril , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[6]  Kumar Biradha,et al.  Molecular paneling via coordination , 2001 .

[7]  Robert N. Goldberg,et al.  Thermodynamic and Nuclear Magnetic Resonance Study of the Reactions of α- and β-Cyclodextrin with Acids, Aliphatic Amines, and Cyclic Alcohols , 1997 .

[8]  Mario Ruben,et al.  Grid-type metal ion architectures: functional metallosupramolecular arrays. , 2004, Angewandte Chemie.

[9]  F. Schmidtchen.  The anatomy of the energetics of molecular recognition by calorimetry: chiral discrimination of camphor by alpha-cyclodextrin. , 2002, Chemistry.

[10]  A. Kaifer,et al.  Cucurbit[7]uril: a very effective host for viologens and their cation radicals. , 2002, Organic letters.

[11]  Jae Wook Lee,et al.  Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. , 2003, Accounts of chemical research.

[12]  A. Kaifer,et al.  Binding selectivity of cucurbit[7]uril: bis(pyridinium)-1,4-xylylene versus 4,4'-bipyridinium guest sites. , 2004, Organic letters.

[13]  Barry B Snushall,et al.  Controlling factors in the synthesis of cucurbituril and its homologues. , 2001, The Journal of organic chemistry.

[14]  Kimoon Kim,et al.  Control of the stoichiometry in host-guest complexation by redox chemistry of guests: inclusion of methylviologen in cucurbit[8]uril. , 2002, Chemical communications.

[15]  M. Borkovec,et al.  A simple thermodynamic model for quantitatively addressing cooperativity in multicomponent self-assembly processes--part 1: Theoretical concepts and application to monometallic coordination complexes and bimetallic helicates possessing identical binding sites. , 2005, Chemistry.

[16]  A. Wego,et al.  The determination of complex stabilities between different cyclodextrins and dibenzo-18-crown-6, cucurbit[6]uril, decamethylcucurbit[5]uril, cucurbit[5]uril, p-tert-butylcalix[4]arene and p-tert-butylcalix[6]arene in aqueous solutions using a spectrophotometric method , 2001 .

[17]  F. Raymo,et al.  Tight inclusion complexation of 2,7-dimethyldiazapyrenium in cucurbit[7]uril , 2005 .

[18]  M. Stödeman,et al.  Structure and dynamic stability of cyclodextrin inclusion complexes with 1,4-disubstituted bicyclo[2.2.2]octanes , 1996 .

[19]  A. Kaifer,et al.  Modes of binding interaction between viologen guests and the cucurbit[7]uril host. , 2004, Organic Letters.