Visual sensing of saccharides promoted by resorcinol condensation products

Organic Letters

Volumn 2, Issue 5, 2000, Pages 589-592

  Lewis, Patrick T ^a   Davis, Claude J ^a   Cabell, Larry A ^a   He, Ming ^a   Read, Mark W ^a   McCarroll, Matthew E ^a   Strongin, Robert M ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001667851     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9903990     Document Type: Article

References (41)

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16. +.
17. (a) Similar products found during detailed investigations of the mechanism of resorcinarene formation: Weinelt, F.; Schneider, H.-J. J. Org. Chem. 1991, 56, 5527.
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19. (c) See also ref 8c.
20. Our synthesis is based directly on similar molecules: Rumboldt, G.; Böhmer, V.; Botta, B.; Paulus, E. V. J. Org. Chem. 1998, 63, 9618.
21. 3:MeOH. Efforts are ongoing in our laboratory aimed at isolating and studying colored materials produced upon heating 1-3.
22. The pH values for Figure 1 were obtained via a pH meter. They therefore represent relative nominal pH readings (to display trends for the present study), not precise pH values.
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41. Addition of 3 equiv of sucrose, glucose, or fructose to colored (preheated) 10% aqueous DMSO solutions containing 5.2 mM 1 affords characteristic color changes (purple, peach, and yellow for sucrose, glucose, and fructose, respectively, as described in ref 5) upon standing at it overnight. Interestingly, addition of preheated (6 min at gentle reflux) 10% aqueous DMSO solutions containing 3 equiv of each of the three sugars to colored (preheated) solutions of 1 also affords solution colors similar to those reported in ref 5, but within l min at room temperature. The absorbance intensity monitored at 538 nm diminishes corresponding to the previously observed order: sucrose (A = 0.546) > glucose (A = 0.493) > fructose (A = 0.174).