A Cucurbituril-Based Gyroscane: A New Supramolecular Form

Day, Anthony I.; Blanch, Rodney J.; Arnold, Arthur P.; Lorenzo, Susan; Lewis, Gareth R.; Dance, Ian G.

doi:10.1002/1521-3757(20020118)114:2<285::aid-ange285>3.0.co;2-6

Cited by 241 publications

(623 citation statements)

References 31 publications

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“…The structure of this remarkable complex was established by X-ray crystallography which demonstrated its resemblance to a gyroscope. 9 Despite the fact that it was not possible to isolate free CB [10] by removal of CB [5], chemical exchange between free and bound CB [5] was demonstrated through the use of 13 C labeled CB [5]. Such molecular gyroscopes and the related molecular ball bearing 116 (CB [7]•I-15) are potential components of future molecular machines.…”

Section: Cb[10]mentioning

confidence: 99%

Cucurbit[n]uril Analogues

2003

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Molecular recognition and self-assembly in aqueous solution have experienced rapid growth in recent years. The use of -, -, and -cyclodextrins, calixarenes, and cyclophanes have served as the platforms for molecular recognition in aqueous solution. Recently, the investigation of an alternative platform based on cucurbituril has become the focus of several research groups. The rigid structure and capability of forming complexes with molecules and ions through hydrophobic, iondipole and hydrogen-bonding interactions make cucurbituril an attractive candidate as a synthetic receptor as well as a building block for the construction of supramolecular architectures.However, before cucurbituril can be used to supplant the more common platforms as the molecule of choice for molecular recognition and self-assembly in aqueous solution, several advances must be made: 1) cucurbiturils must become available in a variety of sizes, 2) their solubility must be improved, and 3) synthetic procedures must be advanced to include the ability to selectively generate specific cucurbituril homologues, derivatives, and analogues. To help rationalize the high yields obtained in these macrocyclization reactions, we performed mechanistic studies of model methylene bridged glycoluril dimers.The molecular recognition properties of a water soluble cucurbit[6]uril analogue in aqueous buffer toward a variety of guests including alkanediamines, aromatics, amino acids, and nucleobases were studied by fluorescence spectroscopy.For the alkanediamines studied, as the length of the alkane is increased between the amines, the association constants also increase. The CB [6] analogue is capable of forming strong complexes with guests containing aromatic rings with association constants (K a ) ranging from 10 2 to 10 6 M -1 due to the favorable -interactions that occur between the host and the aromatic portion of the guest while encapsulated in its hydrophobic cavity. CUCURBIT[N]URIL ANALOGUES

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Section: Cb[10]mentioning

confidence: 99%

Cucurbit[n]uril Analogues

2003

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“…Figure 1) [14][15][16][17]. Recently some efforts have been made to introduce substitution in order to achieve ready solubility in both aqueous systems and common organic solvents, and a number of fully and partially substituted Q[n]s have been reported [18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

“…The novel structure and the capability of forming complexes with molecules and ions make the cucurbit[n]uril family attractive, not only as synthetic receptors but also as building blocks for supramolecular assemblies such as rotaxanes, catenanes, and molecular machines [24][25][26][27][28][29][30]. Nevertheless research on Q[n]s as receptors for anions is scarce [17,31].…”

Section: Introductionmentioning

confidence: 99%

Chlorine Anion Encapsulation by Molecular Capsules Based on Cucurbit[5]uril and Decamethylcucurbit[5]uril

et al. 2007

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“…As part of our ongoing investigation on aminoadamantane derivatives, we present ac ompound containing multiple functional groups that can develop strong intermolecular interactions with cucurbit[n]urils (CB[n]) [1][2][3][4].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of bis[1-adamantane-(1-phenyl)-2-propyleneammonium] tetrachlorozincate, [C19H26N]2[ZnCl4]

Xiao¹,

Wu²,

Zhang³

et al. 2008

Zeitschrift Für Kristallographie - New Crystal Structures

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C 38 H 52 Cl 4 N 2 Zn, monoclinic, P2 1 /n (no. 14), a =14.9150(6) Å, b =15.6147(6) Å, c =17.7489(8) Å, b =114.082(2)°, V =3773.9 Å 3 , Z =4,R gt (F) =0.042, wR ref (F 2 ) =0.104, T =293 K. Source of materialAs olution of 3-phenyl-2-propylene-1-aldehyde (1.36 g, 0.01 mol) in CH 3 OH (50 ml) was added to as tirred solution of 1-aminoadamantane (1.51 g, 0.01 mol) in CH 3 OH (150 ml) on an oil bath at 50°C for 5h ours. To the reaction mixture, NaBH 4 (0.95 g, 0.025 mol) was added in small portions on an ice bath for 8hours. The insoluble residue was removed by filtration and the filtrate was neutralized with HCl to pH of 6-7and filtered again. Excess HCl solution was added into the last filtrate, the solvent was removed, and the residue was added to astirred ethanol solution (300 ml) of ZnCl 2 (0.01 mol, 1.37 g). After stirring for about 2hours, the colorless solution was filtered, and the filtrate was left to stand still. Colorless block-shaped crystals of the complex were formed after slow evaporation of the solvent for three weeks. DiscussionAs part of our ongoing investigation on aminoadamantane derivatives, we present ac ompound containing multiple functional groups that can develop strong intermolecular interactions withThe crystal structure of the title compound consists of the anion complex (ZnCl 4 ) 2-and two 1-adamantane-(1-phenyl)-2-propylene-ammonium cations. The (ZnCl4) 2-anion is adistorted tetrahedron with bond angles ranging from 105.24(3)°to 112.53(4)°and with Zn-Cl bonds ranging from 2.242(1) Å to 2.3021(8) Å.T he dihedral angle between the phenyl ring ( C14®C19 )and the phenyl ring (C33 ®C38 )ofasecond molecule is 59.7(2)°. The N1-C11-C12-C13 and N2-C30-C31-C32 torsion angles are 94.2(5)°and 97.1(4)°, respectively. The intermolecular Hb onds are formed whereas the protonated N1 and N2 atoms act as hydrogen-bond donors and the Cl2 and Cl1 atoms act as hydrogen-bond acceptors, The distance of the N1-H1D···Cl2 i and the N2-H2A···Cl1 i hydrogen bonds are 3.259(3) Å and 3.242(2) Å,respectively (symmetry code i: -1/2+x,-1/2-y,-1/2+z). Layers are formed by cations packed in at ail-to-tail manner, such that the aminoadamantane units are far away from each other. The driving force for this self-assembled structure can be attributed to C-H···p interactions between the aromatic pyridyl rings and the aminoadamantane units. Thus, the crystal structure is built up through acombination of hydrogen bond and C-H···p interactions.

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A Cucurbituril-Based Gyroscane: A New Supramolecular Form

Cited by 241 publications

References 31 publications

Cucurbit[n]uril Analogues

Cucurbit[n]uril Analogues

Chlorine Anion Encapsulation by Molecular Capsules Based on Cucurbit[5]uril and Decamethylcucurbit[5]uril

Crystal structure of bis[1-adamantane-(1-phenyl)-2-propyleneammonium] tetrachlorozincate, [C19H26N]2[ZnCl4]

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