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DOI: 10.1055/s-2004-832817
New Molecular Clips from Diphenylglycoluril and Catechol: Preparation, Structure and Conformation Studies, Binding Properties
Publication History
Publication Date:
24 September 2004 (online)
Abstract
A new molecular clip and its two alkylated derivatives, which are soluble in most of organic solvents, were prepared from hydroxymethylated diphenylglycoluril and catechol. The structure and conformation of these new clips were studied. Their binding properties for dihydroxybenzene were also studied with the aid of 1H NMR titration.
Keywords
diphenylglycoluril - molecular clip - supramolecular assemblies - catechol
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References
Compound 3a: 1H NMR (300 MHz, DMSO-d
6): δ = 9.37 (s, 2 H, OH) and 8.32 (s, 2 H, OH), 7.08 (s, 10 H, ArH), 6.97 (d, 2 H, ArH, J = 8.4 Hz) and 6.48 (d, 2 H, ArH, J = 8.4 Hz), 5.36 and 3.59 (d, 4 H, ArCH2N, J = 15.9 Hz), 4.50 and 3.91 (d, 8 H, ArCH2N, J = 15.9 Hz). 13C NMR (75 MHz, DMSO-d
6): δ = 159.50, 159.06 (urea C=O), 145.24, 143.71, 138.47, 134.90, 134.33, 128.64, 128.53, 128.35, 128.17, 125.18, 113.30, 85.25, 78.73, 45.76, 45.34, 44.94, 37.05. ESI-MS (FAB): m/z = 563 [M + H]+; mp >294 °C. Compound 3b: 1H NMR (CDCl3): δ = 7.08 (s, 10 H, ArH), 6.69 (d, 2 H, ArH, J = 8.4 Hz) and 6.63 (d, 2 H, ArH, J = 8.4 Hz), 5.54 and 3.80 (d, 4 H, ArCH2N, J = 15.9 Hz), 4.72 and 4.09 (d, 4 H, ArCH2N, J = 15.9 Hz), 3.91 (s, 6 H, OCH3) and 3.78 (s, 6 H, OCH3). 13C NMR (75 MHz, CDCl3): δ = 157.70, 157.27 (urea C=O), 151.98, 146.58, 133.80, 131.14, 130.09, 128.73, 128.32, 128.25, 124.98, 110.55, 85.63, 62.50, 61.56, 60.79, 56.31, 56.07, 46.00, 45.78, 38.10. ESI-MS (FAB): m/z = 619 [M + H]+; mp >294 °C. Compound 3c: 1H NMR (CDCl3):
δ = 7.08 (s, 10 H, ArH), 6.91 (d, 2 H, ArH, J = 8.4 Hz) and 6.59 (d, 2 H, ArH, J = 8.4 Hz), 5.59 and 3.76 (d, 4 H, ArCH2N, J = 15.9 Hz), 4.70 and 4.08 (d, 4 H, ArCH2N, J = 15.9 Hz), 4.13 (q, 4 H, OCH2C, J = 10.9 Hz), 3.96 (q, 4 H, OCH2C, J = 10.9 Hz), 1.47-1.37 (br, 12 H, OCCH3). 13C NMR (75 MHz, CDCl3): δ = 158.07, 157.68 (urea C=O), 151.67, 146.49, 134.17, 131.31, 130.19, 128.78, 128.71, 128.51, 128.41, 124.79, 111.68, 85.48, 69.45, 64.17, 45.50, 37.83, 16.06, 15.22. ESI-MS (FAB): m/z = 675 [M + H]+; mp 227.4-228.1 °C.