106319-03-3Relevant articles and documents
A facile one-pot synthesis and the crystal structure of a molecular clip derived from diphenylglycoluril
Wang, Zhi-Guo,Wang, Zi-Hua,Teng, Lei
, p. 949 - 952 (2008)
A facile procedure for the one-pot synthesis of a clip molecule via condensation of diphenylglycoluril, paraformaldehyde, and 4-dimethoxybenzene in the presence of methanesulfonic acid is described. The advantages of this method are mild conditions, single product formation and good yield. Especially, the procedure of the product purification is more simple and convenient. In addition, the clip molecule is characterized by X-ray crystal structure analysis, which shows different weak interactions forces compared to the structure reported previously.
Synthesis, Conformational Analysis, and Binding Properties of Molecular Clips with Two Different Side Walls
Reek, Joost N. H.,Elemans, Johannes A.A.W.,Nolte, Roeland J. M.
, p. 2234 - 2243 (2007/10/03)
A new general route toward the synthesis of diphenylglycoluril clips with two different side walls starting from the new precursor 6b and the known compound 2b is described. A variety of clips are accessible in this way, some of them containing metal binding ligand systems, viz. phenanthroline, pyridine, salophen, and porphyrin for future applications as supramolecular catalysts. The physical and binding properties of the new clips are presented and discussed.
Binding features of molecular clips derived from diphenylglycoluril
Sijbesma,Kentgens,Lutz,Van Der Maas,Nolte
, p. 8999 - 9005 (2007/10/02)
The structure and binding properties of a series of receptor molecules based on the building block diphenylglycoluril are described. These receptors bind dihydroxy-substituted aromatic guests in chloroform solution by means of hydrogen bonding and π-π stacking interactions. IR difference spectroscopy shows that the hydrogen bonds are formed between the OH groups of the guest molecule and the π-electrons of the urea carbonyl groups present in the receptor. The structure of the complexes was further investigated by comparing the complexation-induced shifts in the 1H NMR spectra with the calculated shifts for a number of geometries of the host-guest complexes. These data demonstrate that the guest molecules are clamped within the cavity of the receptor.
Synthesis of concave receptors derived from diphenylglycoluril
Sijbesma, R. P.,Nolte, R. J. M.
, p. 643 - 647 (2007/10/02)
Improved synthtic methods are described for the synthesis of concave receptor molecules.These receptors consist of a diphenylglycoluril unit, flanked by two aromatic moieties.The most versatile synthetic method consists of Lewis-acid-catalyzed reaction of
Binding of Dihydroxybenzenes in a Synthetic Molecular Clip. Effect of Hydrogen Bonding and ?-Stacking
Sijbesma, Rint P.,Kentgens, Arno P. M.,Nolte, Roeland J. M.
, p. 3199 - 3201 (2007/10/02)
A synthetic host, which can easily be assembled starting from urea and benzil, selectively binds resorcinol by hydrogen bonding and ?-stacking.
Synthesis and Binding Properties of Basked-Shaped Hosts
Smeets, Jan W. H.,Sijbesma, Rint P.,Dalen, Lydia van,Spek, Anthony L.,Smeets, Wilberth J. J.,Nolte, Roeland J. M.
, p. 3710 - 3717 (2007/10/02)
We described a novel, concave building block (4) for the synthesis of organic hosts.Compound 4 contains two fused 2-imidazolidone rings, which are flanked by two o-xylylene units.Basked-shaped hosts are constructed by attaching oxyethylene bridges to the
