Type of Document Dissertation Author Johnson, Rolanda Author's Email Address rjohn19@lsu.edu URN etd-01082004-115607 Title The Syntheses of Novel Indicators and Materials for Chiral Separation Degree Doctor of Philosophy (Ph.D.) Department Chemistry Advisory Committee
Advisor Name Title Robert Strongin Committee Chair Bill Crowe Committee Member Steven Watkins Committee Member William Daly Committee Member Warren Johnson Dean's Representative Keywords
- chiral compounds
- indicators
- synthesis
- mechanism
Date of Defense 2003-12-04 Availability restricted 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.
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