Hemicucurbit[6]uril, a selective ligand for the complexation of anions in aqueous solution

Buschmann, Hans‐Jürgen; Cleve, E.; Schollmeyer, Eckhard

doi:10.1016/j.inoche.2004.11.020

Cited by 42 publications

(8 citation statements)

References 19 publications

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“…It is noted that HemiQ [6] has been observed to bind weakly to particular metal cations and solubility tests of this macrocycle in water showed that its solubility is further increased in the presence of metal ions such as Co 2+ , Ni 2+ , and UO 2+ . 204,205 The host-guest chemistry was first studied by investigating the interactions of HemiQ [6] and HemiQ [12] with phenazine hydrochloride (PheH + ). The formation of a stoichiometric exclusion complex of PheH + with HemiQ [6] was observed, and both 1 : 1 and 2 : 1 complexes were detected.…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

Synthesis and separation of cucurbit[n]urils and their derivatives

et al. 2016

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Cucurbit[n]uril chemistry has become an important part of contemporary supramolecular chemistry since cucurbit[n]urils (Q[n]s) are not only able to encapsulate various guests, but are also capable of coordinating to a wide range of metal ions, leading to the establishment of Q[n]-based host-guest chemistry and coordination chemistry. Each of these impressive developments can be attributed to the growth of protocols for obtaining Q[n]s. In this review, we survey synthetic procedures for obtaining cucurbit[n]urils and their substituted derivatives together with the separation and purification of these remarkable compounds. The coverage is aimed at both existing workers in the field as well as at those requiring an "entry" into Q[n]-based research.

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Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

Synthesis and separation of cucurbit[n]urils and their derivatives

et al. 2016

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“…In hemicucurbiturils, on the other hand, monomers are linked together via one bridge, causing a zigzag orientation of the urea functionalities (16 -18). This structural change, compared with the normal cucurbiturils, drastically influences the electronic structure of macrocycles and allows complexation of anions inside the cavity (19,20). The zigzag orientation of the single-bridged glycoluril monomers in bambusurils (21) exhibits similar anion binding properties (22)(23)(24).…”

Section: Introductionmentioning

confidence: 99%

New homologues of chiral cyclohexylhemicucurbit[n]urils

Fomitšenko

Shmatova

Öeren

et al. 2014

Supramolecular Chemistry

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The existence of new 7-, 8-, 9-and 10-membered homologues of chiral cyclohexylhemicucurbituril is reported. The barrelshaped (all-R)-cyclohexylhemicucurbit[8]uril ((all-R)-cycHC[8]) was isolated and its complexes with anions were detected in negative ion mode MS. Here, 7-, 9-and 10-membered homologues were detected by HPLC -HRMS. Geometries of all reported macrocycles were calculated using quantum chemical methods, which showed that even-numbered homologues were barrel-shaped and odd-numbered homologues were asymmetrical barrel-shaped with unequal dimensions of the openings. The size of the ((all-R)-cycHC[8]) cavity was comparable to CB[8] and it probably can serve as a chiral host.

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“…Cucurbit[ n ]urils are constituted of repeated glycoluril units ( n = 5–8, 10) doubly bridged by methylene linkers which ensure the rigidity of the structure around the hydrophobic cavity. They are particularly suitable for the complexation of cations, neutral molecules and gases. ,,, Functionalized CB[ n ] were added to the family as well as hemicucurbit[n]urils (hmCU[ n ]) formed of n ( n = 6, 12) methylene-linked ethyleneurea fragments that have an alternate conformation in solution able to complex anions (Scheme ) …”

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confidence: 99%

Extension of the Bambus[n]uril Family: Microwave Synthesis and Reactivity of Allylbambus[n]urils

2013

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Microwave irradiations allow the preparation of unsaturated bambusurils in 85% yield compared to 20% yield under classical reaction conditions. Five new bambusurils were synthesized including unsaturated derivatives Allyl(8)BU[4] and Allyl(12)BU[6] bearing diallylglycoluril units. The reactivity of Allyl(8)BU[4] was tested in a variety of organic reactions showing that this macrocycle acts as a classical double bond-bearing product. The first monofunctionalized bambusuril Allyl(7)HepBU[4] prepared by a cross metathesis reaction is also reported.

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Hemicucurbit[6]uril, a selective ligand for the complexation of anions in aqueous solution

Cited by 42 publications

References 19 publications

Synthesis and separation of cucurbit[n]urils and their derivatives

Synthesis and separation of cucurbit[n]urils and their derivatives

New homologues of chiral cyclohexylhemicucurbit[n]urils

Extension of the Bambus[n]uril Family: Microwave Synthesis and Reactivity of Allylbambus[n]urils

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