Beilstein J. Org. Chem.2019,15, 1268–1274, doi:10.3762/bjoc.15.124
product. Two disastereomers of the macrocycle were separated and characterized by means of NMR spectroscopy and X-ray crystallography. Conformational changes of these diastereomers were investigated using DFT models and variable-temperature NMR.
Keywords: bambusurils; conformers; glycolurils; macrocycles
urea groups can participate in intermolecular hydrogen bonding resulting in the formation of tubular [5][6][7] or gel-like [8] structures. Ureas lacking of N–H hydrogen atoms such as ethyleneureas, glycolurils, and biotin are also important building blocks of macrocyclic receptors such as cucurbiturils
induced any change in the NMR spectra of the macrocycles. This indicates that these macrocycles do not bind the studied anions. We assume that the cavity of the macrocycles is too small to be able to include any anions. Indeed the conformer 1b-1 with two facing glycolurils resembles the bambus[4]uril
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Graphical Abstract
Scheme 1:
Reaction of 2,4-dimethylglycoluril and m-xylylene dibromide.
Beilstein J. Org. Chem.2009,5, No. 79, doi:10.3762/bjoc.5.79
λexc = 318 nm. For comparison, the emission of the permanently twisted, o-substituted stilbene 5 (λexc = 300 nm) is also shown [9].
Can the fluorescence of the encapsulated stilbene be restored? When suitable guests are present, addition of glycolurils such as 7 to solutions of 1.1 generates extended
capsule 1.74.1 (Figure 3) [10]. The glycolurils are arranged in a chiral manner, in either cycloenantiomer of the extended capsule. The glycolurils force the two square prisms of 1.74.1 into registry (Figure 3A). That is, the square prisms are now aligned and stilbene as well as related guests may be
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Graphical Abstract
Figure 1:
(Top) Tetraimide cavitand 1, the dimeric capsule 1.1 and its cartoon representation. (Bottom) The s...