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Synlett 2004(13): 2385-2387  
DOI: 10.1055/s-2004-832817
LETTER
© Georg Thieme Verlag Stuttgart · New York

New Molecular Clips from Diphenylglycoluril and Catechol: Preparation, Structure and Conformation Studies, Binding Properties

Qing-Sheng Liu, Shu-Ling Gong, Yan Ding, Yuan-Yin Chen*, Xiao-Jun Wu
Department of Chemistry, Wuhan University, Wuhan 430072, P. R. China
Fax: +86(27)87647617; e-Mail: yychen@whu.edu.cn;
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Publication History

Received 15 July 2004
Publication Date:
24 September 2004 (online)

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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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8

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.