Abstract
Cucurbit[n]urils (Q[n]) are promising ligands for the coordination of metal ions, metal complexes or clusters, and form various Q[n]-based complexes. Among the Q[n] complexes, those formed by direct coordination between Q[n]s and metal ions are particularly important. The direct coordination of metal ions to cucurbit[n]urils leads to the formation of Q[n]-based molecular capsules, tubular polymers and molecular bracelets, which could have nanoscale applications in drug delivery, molecular devices and new materials.
Similar content being viewed by others
References
Green J E, Choi J W, Boukai A, et al. A 160-kilobit molecular electronic memory patterned at 1011 bits per square centimeter. Nature, 2007, 445: 414–417
Griffiths K E, Stoddart J F. Template-directed synthesis of donor/acceptor [2]catenanes and [2]rotaxanes. Pure Appl Chem, 2008, 80: 485–506
Passaniti P, Ceroni P, Balzani V, et al. Amide-based molecular knots as platforms for fluorescent switches. Chem Eur J, 2006, 12: 5685–5690
Philp D, Stoddart J F. Self-assembly in natural and unnatural systems. Angew Chem Int Ed, 1996, 35: 1154–1196
Ghadiri M R, Granja J R, Milligan R A, et al. Self-assembling organic nanotubes based on a cyclic peptide architecture. Nature, 1993, 366: 324–327
Iijima S. Helical microtubules of graphitic carbon. Nature, 1991, 354: 56–58
Sakai N, Mareda J, Matile S. Rigid-rod molecules in biomembrane models: From hydrogen-bonded chains to dynthetic multifunctional pores. Acc Chem Res, 2005, 38: 79–87
Abrahams B F, Hoskins B F, Michail D M, et al. Assembly of porphyrin building blocks into network structures with large channels. Nature, 1994, 369: 727–729
Subramanian S, Zaworotko M J. Porous solids by design: [Zn(4,4’-bpy)2(SiF6)]n·xDMF, a single framework octahedral coordination polymer with large square channels. Angew Chem Int Ed Engl, 1995, 34: 2127–2129
Yaghi O M, Li G, Li H. Selective binding and removal of guests in a microporous metal-organic framework. Nature, 1995, 378: 703–706
Yaghi O M, Davis C E, Li G, et al. Selective guest binding by tailored channels in a 3-D porous Zinc(II)-1,3,5-benzenetricarboxylate network. J Am Chem Soc, 1997, 119: 2861–2868
Li H, Davis C E, Groy T L, et al. Coordinatively unsaturated metal centers in the extended porous framework of Zn3(BDC)3·6CH3OH (BDC = 1,4-benzenedicarboxylate). J Am Chem Soc, 1998, 120: 2186–2187
Harada A, Li J, Kamachi M. The molecular necklace: A rotaxane containing many threaded α-cyclodextrins. Nature, 1992, 356: 325–327
Harada A, Li J, Kamachi M. Synthesis of a tubular polymer from threaded cyclodextrins. Nature, 1993, 364: 516–518
Sakai N, Brennan K C, Weiss L A, et al. Nucleophilic attack of hydroxide on a Mn(V) oxo Complex, a model of the O-O bond formation in the OEC of PS II. J Am Chem Soc, 1997, 119: 8726–8727
Weiss L A, Sakai N, Ghebremariam B, et al. Functional nonpeptide models for transmembrane proton channels. J Am Chem Soc, 1997, 119: 12142–12149
Sakai N, Majumdar N, Matile S. Self-assembled rigid-rod ionophores. J Am Chem Soc, 1999, 121: 4294–4295
Horner M J, Holman K T, Ward M D. Architectural diversity and elastic networks in hydrogen-bonded host frameworks: From molecular jaws to cylinders. J Am Chem Soc, 2007, 129: 14640–14660
Behrend R, Meyer E, Rusche F. Mittheilungen aus dem organischchemischen laboratorium der technischen hochschule zu hannover. Justus Liebigs Ann Chem, 1905, 339: 1–5
Freeman W A, Mock W L, Shih N Y. Cucurbituril. J Am Chem Soc, 1981, 103: 7367–7368
Kim J, Jung I S, Kim S Y, et al. New cucurbituril homologues: Syntheses, isolation, characterization, and X-ray crystal structures of cucurbit[n]uril (n = 5, 7, and 8). J Am Chem Soc, 2000, 122: 540–541
Day A I, Arnold A P. Method for synthesis cucurbiturils. WO 0068232, 2000. 8
Day A, Arnold A P, Blanch R J, et al. Controlling factors in the synthesis of cucurbituril and its homologues. J Org Chem, 2001, 66: 8094–8100
Day A I, Blanch R J, Arnold A P, et al. The first endoannular metal halide-cucurbituril: cis-SnCl4(OH2)2-cucurbit[7]uril. Angew Chem Int Ed, 2002, 41: 275–279
Wang W, Kaifer A E. Cucurbituril and cyclodextrin complexes of dendrimers. Adv Polym Sci, 2009, 222: 205–235
Yang H, Tan Y, Huang X, et al. Research progress of cucurbiturils. Prog Chem, 2009, 21: 164–173
Martini G, Ciani L. Electron spin resonance spectroscopy in drug delivery. Phys Chem Chem Phys, 2009, 11: 211–254
Nau W M, Hennig A, Koner A L. Squeezing fluorescent dyes into nanoscale containersem dash The supramolecular approach to radiative decay engineering. Springer Ser Fluorece, 2008, 4: 185–211
Ko Y H, Kim E, Hwang I, et al. Supramolecular assemblies built with host-stabilized charge-transfer interactions. Chem Commun, 2007: 1305–1315
Huang F, Gibson H W. Polypseudorotaxanes and polyrotaxanes. Prog Polym Sci, 2005, 30: 982–1018
Arunkumar E, Forbes C C, Mith B D. Improving the properties of organic dyes by molecular encapsulation. Eur J Org Chem, 2005: 4051–4059
Mukhopadhyay P, Wu A, Isaacs L. Social self-sorting in aqueous solution. J Org Chem, 2004, 69: 6157–6164
Kim K. Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies. Chem Soc Rev, 2002, 31: 96–107
Elemans J A A W, Rowan A E, Nolte R J M. Self-assembled architectures from glycoluril. Ind Eng Chem Res, 2000, 39: 3419–3428
Gerasko O A, Sokolov M N, Fedin V P. Mono- and polynuclear aqua complexes and cucurbit[6]uril: Versatile building blocks for supramolecular chemistry. Pure Appl Chem, 2004, 76: 1633–1646
Samsonenko D G, Gerasko O A, Virovets A V, et al. Synthesis and crystal structure of a supramolecular adduct of trinuclear molybdenum oxocluster with macrocyclic cavitand cucurbit[5]uril containing the included ionic associate Na+...Cl...Na+. Russ Chem Bull, 2005, 54: 1557–1562
Liu J X, Long L S, Huang R B, et al. Molecular capsules based on cucurbit[5]uril encapsulating “naked” anion chlorine. Cryst Growth Des, 2006, 6: 2611
Shao Y, Li Y Z, Shi J P, et al. [μ-Cucurbit[6]uril(2-)]bis [pentaaquacalcium(II)] bis[tetrachloridozincate(II)]heptahydrate. Acta Crys, 2007, E63: m1480
Kasuga N C, Umeda M, Kidokoro H, et al. Four novel solid-state supramolecular assemblies constructed from decavanadate salts and decamethylcucurbit[5]uril. Cryst Growth Des, 2009, 9: 1494–1498
Heo J, Kim J, Whang D, et al. Columnar one-dimensional coordination polymer formed with a metal ion and a host-guest complex as building blocks: Potassium ion complexed cucurbiturils. Inorg Chim Acta, 2000, 297: 307–312
Yan K, Huang Z X, Liu S M, et al. Synthesis and crystal structure of new supramolecular adducts of [PtCl6]2+ with cucurbit[7]uril: [(H3O)2(PtCl6)]3(C42H42N28O14)2·H2O. Wuhan Uni J Nat Sci, 2004, 9: 99–101
Mitkina T V, Naumov D Y, Gerasko O A, et al. Inclusion of nickel(II) and copper(II) complexes with aliphatic polyamines in cucurbit[8]uril. Russ Chem Bull, 2004, 53: 2519–2524
Liu J X, Dong C H, Long L S, et al. From 1D zigzag chain to 1D tubular structure, weak field ligand-dependent assembly of cucurbit[6] uril-based tubular coordination polymer. Dalton Trans, 2009: 7344–7346
Tripolskaya A A, Mainicheva E A, Mitkina T V, et al. Sc(III), Eu(III), and Gd(III) complexes with macrocyclic cavitand cucurbit[6]uril: Synthesis and crystal structures. Russ J Coord Chem, 2005, 31: 768–774
Mainicheva E A, Tripolskaya A A, Gerasko O A, et al. Synthesis and crystal structures of PrIII and NdIII complexes with the macrocyclic cavitand cucurbit[6]uril. Russ Chem Bull, 2006, 55: 1566–1573
Tripol’skaya A A, Mainicheva E A, Geras’ko O A, et al. Synthesis and crystal structure of a supramolecular adduct of the aqua nitrato complex of gadolinium [Gd(NO3)(H2O)7]2+ with macrocyclic cavitand cucurbit[6]uril. J Struct Chem, 2007, 48: 547–551
Gerasko O A, Mainicheva E A, Naumova M I, et al. Tetranuclear lanthanide aqua hydroxo complexes with macrocyclic ligand cucurbit[6]uril. Eur J Inorg Chem, 2008: 416–424
Thuéry P. Uranyl ion complexes with cucurbit[n]urils (n = 6, 7, and 8): A new family of uranyl-organic frameworks. Cryst Growth Des, 2008, 8: 4132–4143
Gerasko O A, Mainicheva E A, Naumova M I, et al. Sandwich-type tetranuclear lanthanide complexes with cucurbit[6]uril: From molecular compounds to coordination polymers. Inorg Chem, 2008, 47: 8869–8880
Thuery P. Uranyl-lanthanide heterometallic complexes with cucurbit[6]uril and perrhenate ligands. Inorg Chem, 2009, 48: 825–827
Thuery P. Lanthanide complexes with cucurbit[n]urils (n = 5, 6, 7) and perrhenate ligands: New examples of encapsulation of perrhenate anions. Inorg Chem, 2009, 48: 4497–4513
Hernandez-Molina R, Sokolov M N, Sykes A G. Behavioral patterns of heterometallic cuboidal derivatives of [M3Q4(H2O)9]4+ (M) Mo, W; Q) S, Se). Acc Chem Res, 2001, 34: 223–230
Hernandez-Molina R, Sokolov M, Esparza P, et al. Aqueous solution chemistry of [Mo3CuSe4]n + (n = 4, 5) and [W3CuQ4]5+ (Q = S, Se) clusters. Dalton Trans, 2004: 847–851
Fedin V P. New lines of research in chemistry of chalcogenide complexes from culusters to supramolecular compounds. Russ J Coord Chem, 2004, 30: 151–158
Hernandez-Molina R, Sokolov M N, Clausen M, et al. Synthesis and structure of Nickel-containing cuboidal clusters derived from [W3Se4(H2O)9]4+: Site-differentiated substitution at the Nickel site in the series [W3NiQ4(H2O)10]4+ (Q = S, Se). Inorg Chem, 2006, 45: 10567
Chubarova E V, Sokolov M N, Samsonenko D G, et al. Supramolecular compounds of chloroaquacomplexes [Mo3Q4-(H2O)9−x Clx](4−x)+ (Q = S, Se; x = 2, 3, 5) with cucurbit[n]urils. J Struct Chem, 2006, 47: 939–945
Hernandez-Molina R, Kalinina I, Sokolov M, et al. Synthesis, structure and reactivity of cuboidal-type cluster aqua complexes with W3PdS4 4+ core. Dalton Trans, 2007: 550–557
Abramov P A, Sokolov M N, Virovets A V, et al. Synthesis and crystal structure of cucurbit[6]uril adduct of hydrogen-bonded cluster complex [Mo3(μ3-Se)(μ2-O)3(H2O)6Cl3]+. J Clust Sci, 2007, 18: 597–605
Hernandez-Molina R, Kalinina I V, Sokolov M N, et al. Studies on Iron-containing chalcogenide clusters with core M3FeQ4 (M = Mo, W; Q=S, Se). Synth React Inorg M, 2007, 37: 765–770
Algarra A G, Sokolov M N, Gonzalez-Platas J, et al. Synthesis, reactivity, and kinetics of substitution in W3PdSe4 cuboidal clusters: A reexamination of the kinetics of substitution of the related W3S4 cluster with thiocyanate. Inorg Chem, 2009, 48: 3639–3649
Gushchin A L, Ooi B, Harris P, et al. Synthesis and characterization of mixed chalcogen triangular complexes with new Mo3(μ3-S)(μ2-Se2)3 4+ and M3(μ3-S)(μ2-Se)3 4+ (M = Mo, W) cluster cores. Inorg Chem, 2009, 48: 3832–3839
Yang H, Tan Y, Huang X, et al. Research progress of cucurbiturils. Prog Chem, 2009, 21: 164–173
Lagona J, Mukhopadhyay P, Chakrabarti S, et al. The cucurbit[n]uril family. Angew Chem Int Ed, 2005, 44: 4844–4870
Gerasko O A, Samsonenko D G, Fedin V P. Supramolecular chemistry of cucurbiturils. Russ Chem Rev, 2002, 71: 741–760
Han B H, Liu Y. Molecular recognition and assembly of cucurbiturils. Chin J Org Chem, 2003, 23: 139–149
Cram D J. Molecular container compounds. Nature, 1992, 356: 26–29
Jeon Y M, Kim J, Whang D, et al. Molecular container assembly capable of controlling binding and release of its guest molecules: Reversible encapsulation of organic molecules in sodium ion complexed cucurbiturils. J Am Chem Soc, 1996, 118: 9790–9791
Whang D, Heo J, Park J H, et al. A molecular bowl with metal ion as bottom: Reversible inclusion of organic molecules in cesium ion complexed cucurbiturils. Angew Chem Int Ed, 1998, 37: 78–80
Beer P D, Gale P A. Anion recognition and sensing: The state of the art and future perspectives. Angew Chem Int Ed, 2001, 40: 486–516
Bondy C R, Gale P A, Loeb S J. Metal-organic anion receptors: Arranging urea hydrogen-bond donors to encapsulate sulfate ions. J Am Chem Soc, 2004, 126: 5030–5031
Dolomanov O V, Blake A J, Champness N R, et al. A novel synthetic strategy for hexanuclear supramolecular architectures. Chem Com mun, 2003: 682–683
Zhou F G, Wu L H, Lu X J, et al. Molecular capsules based on methyl-substituted cucurbit[5]urils and strontium-capped. J Mol Struct, 2009, 927: 14–20
Zhao Y J, Xue S F, Zhu Q J, et al. Synthesis of a symmetrical tetrasubstituted cucurbit[6]uril and its host-guest inclusion complex with 2,2′-bipyridine. Chinese Sci Bull, 2004, 49: 1111–1116
Thuery P, Masci B. Uranyl ion complexation by cucurbiturils in the presence of perrhenic, phosphoric, or polycarboxylic acids: Novel mixed-ligand Uranyl-organic frameworks. Cryst Growth Des, 2010, 10: 716–725
Heo J, Kim S Y, Whang D, et al. Shape-induced, hexagonal, open frameworks: Rubidium ion complexed cucurbiturils. Angew Chem Int Ed, 1999, 38: 641–643
Zhang F, Yajima T, Li Y Z, et al. Iodine-assisted assembly of helical coordination polymers of cucurbituril and asymmetric copper(ii) complexes. Angew Chem Int Ed, 2005, 44: 3402–3407
Samsonenko D G, Gerasko O A, Lipkowski J, et al. Synthesis and crystal structure of the nanosized supramolecular SmIII complex with macrocyclic cavitand cucurbituril {[Sm(H2O)4]2(C36H36N24O12)3}Br6· 44H2O. Russ Chem Bull, 2002, 51: 1915–1918
Choudhury S D, Mohanty J, Pal H. Cooperative metal ion binding to a cucurbit[7]uril-thioflavin T complex: Demonstration of a stimulus-responsive fluorescent supramolecular capsule. J Am Chem Soc, 2010, 132: 1395–1401
Ko Y H, Kim K, Kang J K, et al. Designed self-assembly of molecular necklaces using host-stabilized charge-transfer interactions. J Am Chem Soc, 2004, 126: 1932–1933
Ni X L, Lin J X, Zheng Y Y, et al. Supramolecular bracelets and interlocking rings elaborated through the interrelationship of neighboring chemical environments of alkyl-substitution on cucurbit[5]uril. Cryst Growth Des, 2008, 8: 3446–3450
Lee E, Heo J, Kim K. A three-dimensional polyrotaxane network. Angew Chem Int Ed, 2000, 39: 2699–2701
Author information
Authors and Affiliations
Corresponding authors
About this article
Cite this article
Cong, H., Zhu, Q., Xue, S. et al. Direct coordination of metal ions to cucurbit[n]urils. Chin. Sci. Bull. 55, 3633–3640 (2010). https://doi.org/10.1007/s11434-010-4146-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11434-010-4146-8