Identifier

etd-01082004-115607

Degree

Doctor of Philosophy (PhD)

Department

Chemistry

Document Type

Dissertation

Abstract

The colorimetric properties of resorcinarene solutions had not been fully investigated since von Baeyer's initial synthesis. We find that the solutions containing resorcinarene macrocycles develop color upon heating or standing. In the presence of saccharides, these solutions exhibit significant color changes which are readily observable by visual inspection. We determined 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 have applied these mechanistic insights towards the challenging problems of the visual detection of saccharides and other important biologically analytes. In addition, we also report the first single crystal X-ray crystal structure determination of a rarely observed "diamond" resorcinarene stereoisomer. The visual sensing of saccharides is of importance to medical diagnostics and industry. The synthesis of the diamine tripod and the diamine fluorescein compounds will be presented and their application towards the detection of saccharides and biomolecules of interest will be discussed. In addition to this, the synthesis of a new cationic chiral surfactant, the l-arginine methyl ester, for use in chiral separations will also be presented.

Date

2004

Document Availability at the Time of Submission

Student has submitted appropriate documentation to restrict access to LSU for 365 days after which the document will be released for worldwide access.

Committee Chair

Robert Strongin

Included in

Chemistry Commons

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