Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry.

The supramolecular chemistry of cucurbituril, a synthetic receptor, is fascinating because of the remarkable guest binding behavior of the host. Studies in the field, however, have met with limitations, since the only species known was the hexameric macrocyclic compound, cucurbit[6]uril. Recently we synthesized its homologues, cucurbit[n]uril (n = 5, 7, 8), and derivatives. These new members of the cucurbituril family have expanded the scope further, and interest in them has grown enormously. This Account is a compilation of recent literature covering the syntheses of the homologues and derivatives, and their supramolecular chemistry.

[1]  H. Holdt,et al.  Cucurbit[5]uril, Decamethylcucurbit[5]uril and Cucurbit[6]uril. Synthesis, Solubility and Amine Complex Formation , 2001 .

[2]  I. Dance,et al.  A cucurbituril-based gyroscane: a new supramolecular form. , 2002, Angewandte Chemie.

[3]  Kimoon Kim,et al.  A kinetically controlled molecular switch based on bistable [2]rotaxane , 2001 .

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

[5]  J. Anderson,et al.  Encapsulation of N(2), O(2), methanol, or acetonitrile by decamethylcucurbit[5]uril(NH(4)(+))(2) complexes in the gas phase: influence of the guest on "lid" tightness. , 2001, Journal of the American Chemical Society.

[6]  A. Day,et al.  The Effects of Alkali Metal Cations on Product Distributions in Cucurbit[n]uril Synthesis , 2002 .

[7]  Kimoon Kim,et al.  Transition metal ion directed supramolecular assembly of one- and two-dimensional polyrotaxanes incorporating cucurbituril. , 2002, Chemistry.

[8]  Kimoon Kim,et al.  Cucurbit[n]uril Derivatives Soluble in Water and Organic Solvents. , 2001, Angewandte Chemie.

[9]  Kimoon Kim,et al.  Molecular Container Assembly Capable of Controlling Binding and Release of Its Guest Molecules: Reversible Encapsulation of Organic Molecules in Sodium Ion Complexed Cucurbituril , 1996 .

[10]  R. Behrend,et al.  I. Ueber Condensationsproducte aus Glycoluril und Formaldehyd , 1905 .

[11]  David J. Williams,et al.  Decamethylcucurbit[5]uril† , 1992 .

[12]  Y. Miyahara,et al.  "Molecular" molecular sieves: lid-free decamethylcucurbit[5]uril absorbs and desorbs gases selectively. , 2002, Angewandte Chemie.

[13]  Kimoon Kim,et al.  Ternary Complexes Between DNA, Polyamine, and Cucurbituril: A Modular Approach to DNA-Binding Molecules. , 2000, Angewandte Chemie.

[14]  Y. Ko,et al.  Novel Pseudorotaxane-Terminated Dendrimers: Supramolecular Modification of Dendrimer Periphery We gratefully acknowledge the Korean Ministry of Science and Technology (Creative Research Initiative Program) for support of this work, and Professor P. K. Bharadwaj for reading the manuscript. , 2001, Angewandte Chemie.

[15]  Eunsung Lee,et al.  A Three‐Dimensional Polyrotaxane Network , 2000 .

[16]  P. Ashton,et al.  Molecular Necklace: Quantitative Self-Assembly of a Cyclic Oligorotaxane from Nine Molecules , 1998 .

[17]  W. Nau,et al.  Polarizabilities Inside Molecular Containers This work was supported by the Swiss National Science Foundation (projects 620-58000.99 and 4047-057552) within the program NFP 47 "Supramolecular Functional Materials". , 2001, Angewandte Chemie.

[18]  W. L. Mock,et al.  Catalysis by cucurbituril. The significance of bound-substrate destabilization for induced triazole formation , 1989 .

[19]  Y. Lim,et al.  Self-assembled ternary complex of cationic dendrimer, cucurbituril, and DNA: noncovalent strategy in developing a gene delivery carrier. , 2002, Bioconjugate chemistry.

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

[21]  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 .

[22]  P. K. Bharadwaj,et al.  Supramolecular amphiphiles: spontaneous formation of vesicles triggered by formation of a charge-transfer complex in a host. , 2002, Angewandte Chemie.

[23]  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.

[24]  A. Wego,et al.  Complex Formation between Cucurbit[n]urils and Alkali, Alkaline Earth and Ammonium Ions in Aqueous Solution , 2001 .

[25]  Kentaro Yamaguchi,et al.  Rotaxane-based molecular switch with fluorescence signaling , 2000 .

[26]  T. White,et al.  Cucurbit[7]uril ando-Carborane Self-Assemble to Form a Molecular Ball Bearing , 2002 .

[27]  M. Jekel,et al.  Cucurbituril for water treatment. Part I: Solubility of cucurbituril and sorption of reactive dyes. , 2001, Water research.

[28]  E. Nakamura,et al.  Synthesis of disubstituted cucurbit[6]uril and its rotaxane derivative. , 2002, Organic letters.

[29]  J. Fettinger,et al.  Diastereoselective formation of glycoluril dimers: isomerization mechanism and implications for cucurbit[n]uril synthesis. , 2002, Journal of the American Chemical Society.

[30]  I. Dance,et al.  A Cucurbituril-Based Gyroscane: A New Supramolecular Form This research was supported by the Australian Research Council and the University of New South Wales. G.R.L. acknowledges the award of a Royal Society Fellowship tenable in Australia. , 2002 .

[31]  Kimoon Kim,et al.  Self-assembly of a polyrotaxane containing a cyclic ''bead'' in every structural unit in the solid state: Cucurbituril molecules threaded on a one-dimensional coordination polymer , 1996 .

[32]  I. Dance,et al.  The first endoannular metal halide–cucurbituril: cis-SnCl4(OH2)2@cucurbit[7]uril , 2001 .

[33]  R. M. Izatt,et al.  A highly selective compound for lead : Complexation studies of decamethylcucurbit[5]uril with metal ions , 2000 .

[34]  Angel E. Kaifer,et al.  Reactive Pseudorotaxanes: Inclusion Complexation of Reduced Viologens by the Hosts β-Cyclodextrin and Heptakis(2,6-di-o-Methyl)-β-Cyclodextrin , 1997 .

[35]  Kimoon Kim,et al.  Selective Inclusion of a Hetero-Guest Pair in a Molecular Host: Formation of Stable Charge-Transfer Complexes in Cucurbit[8]uril. , 2001, Angewandte Chemie.

[36]  Kimoon Kim,et al.  Rotaxane dendrimers. , 2003, Topics in current chemistry.

[37]  Stoddart,et al.  Artificial Molecular Machines. , 2000, Angewandte Chemie.

[38]  Kimoon Kim,et al.  Macrocycles within Macrocycles: Cyclen, Cyclam, and Their Transition Metal Complexes Encapsulated in Cucurbit[8]uril. , 2001, Angewandte Chemie.

[39]  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.

[40]  Kimoon Kim,et al.  Polycatenated Two-Dimensional Polyrotaxane Net , 1997 .

[41]  Kimoon Kim,et al.  Synthesis of a Five-Membered Molecular Necklace: A 2+2 Approach. , 1999, Angewandte Chemie.

[42]  Kimoon Kim,et al.  Designed self-assembly of molecular necklaces. , 2002, Journal of the American Chemical Society.