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 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.
He
Ming
M
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
Johnson
Rolanda J
RJ
Escobedo
Jorge O
JO
Beck
Patricia A
PA
Kim
Kyu Kwang
KK
St  Luce
Nadia N
NN
Davis
Claude J
CJ
Lewis
Patrick T
PT
Fronczek
Frank R
FR
Melancon
Bruce J
BJ
Mrse
Anthony A
AA
Treleaven
W Dale
WD
Strongin
Robert M
RM
D001897:Boronic Acids / Q000737:chemistry; D002240:Carbohydrate Sequence; D003124:Colorimetry; D018360:Crystallography, X-Ray; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction; D012118:Resorcinols / Q000737:chemistry*; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet; D014966:Xanthenes / Q000737:chemistry
D001897:Boronic Acids; D009005:Monosaccharides; D009844:Oligosaccharides; D012118:Resorcinols; D012996:Solutions; D014966:Xanthenes; D008320:Maltose; D004121:Dimethyl Sulfoxide