Molecular clips and cages derived from glycoluril

Sijbesma, RP Rint; Nolte, Roeland J. M.

doi:10.1007/3-540-58800-0_17

Cited by 40 publications

(10 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Further contributions and examples representing the different types of such molecules with open cavities were published by the groups of Vögtle [495], Rebek [496], Nolte [497], Harmata [498–499 518], Chen [500], Klärner [486,501–503] and Schrader (see the discussed example, Fig. 112).…”

Section: Reviewmentioning

confidence: 99%

“…Cations and some alkyl or a variety of aromatic guests, especially electron deficient aromatic systems [501,504–507] can be co-ordinated by dispersive forces such as π–π, CH–π- and cation–π-interaction. The introduction of polar functionality enables the binding of guests by additional interactions, for example, 1,3-dihydroxybenzene [497] by H-bonding or nucleosides [508–512] by ionic interactions. Similarly, ammonium ions, diamines [513–514] or chiral guests [515] can be recognized by appropriate functional groups arranged on these scaffolds.…”

Section: Reviewmentioning

confidence: 99%

See 1 more Smart Citation

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

215

130

View full text Add to dashboard Cite

SummaryAmmonium ions are ubiquitous in chemistry and molecular biology. Considerable efforts have been undertaken to develop synthetic receptors for their selective molecular recognition. The type of host compounds for organic ammonium ion binding span a wide range from crown ethers to calixarenes to metal complexes. Typical intermolecular interactions are hydrogen bonds, electrostatic and cation–π interactions, hydrophobic interactions or reversible covalent bond formation. In this review we discuss the different classes of synthetic receptors for organic ammonium ion recognition and illustrate the scope and limitations of each class with selected examples from the recent literature. The molecular recognition of ammonium ions in amino acids is included and the enantioselective binding of chiral ammonium ions by synthetic receptors is also covered. In our conclusion we compare the strengths and weaknesses of the different types of ammonium ion receptors which may help to select the best approach for specific applications.

show abstract

Section: Reviewmentioning

confidence: 99%

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

215

130

View full text Add to dashboard Cite

show abstract

“…As an interesting research objective, glycoluril units are widely used to design interesting supramolecular structures due to their concave skeletons. 9–12 These versatile molecules are designed as host molecules with cavities such as molecular capsules, 13,14 the cucurbit[n]uril family of macrocycles 15–17 and analogues, 18 or with semi-cavities such as molecular clips. 19,20 Among them, clip-shaped glycoluril derivatives have attracted much interest due to their ability to function as excellent receptors.…”

Section: Introductionmentioning

confidence: 99%

X-ray structure of an unusual glycoluril derivative conformation: Structural analysis and influencing factors

Wang

Yang

Zou

et al. 2020

Journal of Chemical Research

View full text Add to dashboard Cite

The synthesis and X-ray structure of a novel glycoluril derivative are described. The crystal of the glycoluril derivative is obtained by slow evaporation in a refrigerator at about 5 °C. X-ray crystallographic analysis revealed that the compound crystallized in an unusual as conformation instead of the usual clip-shaped aa conformation. Structural analysis shows that the solvation effect, hydrogen bonding, and space-occupying effect influenced the crystallization conformation of the derivative. The X-ray crystallographic analysis in this work provides additional crystallographic evidence of the as conformation of the 3U glycoluril derivative and shows the effect of solvent water on the conformational behavior.

show abstract

“…1,3,4,6-tetrachloro-3a,6a-diphenylglycoluril [12], [13] and 1,3,4,6-tetrachloro-3a,6a-dimethylglycoluril [13], [14] were therefore published and patented. Further application of glycoluriles was found as whitening agents [15][16][17] as well as rigid structural units in supramolecular chemistry [18][19][20][21][22]. In our short communication [1], we wrote about criss-cross cycloadditions to some 1,4-disubstituted 1,4-diazabuta-1,3-dienes (1) as an easy and cheap way to obtain mixed 1,4-disubstituted 5-thioxoperhydroimidazo [4,5-d]imidazole-2-ones (3) (monothioglycoluriles).…”

Section: Introductionmentioning

confidence: 99%