Chromophore Formation in Resorcinarene Solutions and the Visual Detection of Mono- and Oligosaccharides

The colorimetric properties of resorcinarene solutions had not been investigated since Baeyer's initial synthesis. We recently reported that solutions containing resorcinarene macrocycles develop color upon heating or standing. In the presence of saccharides, these solutions exhibit significant...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-05, Vol.124 (18), p.5000-5009
Main Authors: He, Ming, Johnson, Rolanda J, Escobedo, Jorge O, Beck, Patricia A, Kim, Kyu Kwang, St. Luce, Nadia N, Davis, Claude J, Lewis, Patrick T, Fronczek, Frank R, Melancon, Bruce J, Mrse, Anthony A, Treleaven, W. Dale, Strongin, Robert M
Format: Article
Language:English
Subjects:
Boronic Acids - chemistry
Carbohydrate Sequence
Chemistry
Colorimetry
Crystallography, X-Ray
Dimethyl Sulfoxide - chemistry
Exact sciences and technology
General and physical chemistry
Magnetic Resonance Spectroscopy
Maltose - chemistry
Molecular Sequence Data
Molecular Structure
Monosaccharides - chemistry
Oligosaccharides - chemistry
Oxidation-Reduction
Resorcinols - chemistry
Solution properties
Solutions
Spectrophotometry, Ultraviolet
Xanthenes - chemistry
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Summary:The colorimetric properties of resorcinarene solutions had not been investigated since Baeyer's initial synthesis. We recently reported that solutions containing resorcinarene macrocycles develop color upon heating or standing. In the presence of saccharides, these solutions exhibit significant color changes which are easily seen. We herein present strong evidence that the solution color is due to macrocycle ring opening and oxidation. The optical responses to saccharides are due to complexation of the sugar with the acyclic chromophores. We apply these mechanistic insights toward the challenging problem of the visual detection of neutral oligosaccharides by simple chromogens. In addition, we also report the first single-crystal X-ray crystal structure determination of a rarely observed “diamond” resorcinarene stereoisomer.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja017713h