Date of Award

1999

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Isiah M. Warner

Second Advisor

Philip W. West

Abstract

The research presented in this dissertation involves spectroscopic studies of cyclodextrin complexation reactions with various guest molecules. Chapter 1 provides an introduction that forms the basis for the remaining chapters. The topics covered in the introduction include the structures and properties of cyclodextrins with a brief section specifically dedicated to solid cyclodextrin. In addition, the environmental applications of cyclodextrins are discussed. The last part of the introduction concerns the theory and applications of fluorescence spectroscopy. In Chapter 2, the extraction of volatile polycyclic aromatic hydrocarbons (PAHs) from air by use of solid cyclodextrin is presented. Naphthalene was chosen as the model compound due to its high vapor pressure. The effect of various alcohols on the gas-solid complexation reactions of PAHs as well as quantitative studies are also reported in this chapter. These studies with the solid cyclodextrin are compared to those examined in aqueous solutions. Chapter 3 pertains to the effect of cyclodextrins on excited state proton transfer reactions of carboxylic acid compounds. Several naphthoic and anthroic acids including 2-naphthoic acid, 1-hydroxy-2-naphthoic acid, 9-anthroic acid, and 2-anthroic acid are studied in order to propose mechanisms for these compounds in monomeric and polymeric cyclodextrins. The inner cavity diameters of the cyclodextrins play a major role in the proposed mechanisms. Chapter 4 reports the effect of the Cyclodextrin Host Isolation Matrix (CHIM) method on excited state proton transfer reactions. These studies involve solid samples of the compounds mentioned in Chapter 3 with the addition of 3-hydroxy-2-naphthoic acid. The CHIM method mimics the spectroscopy of isolated molecules. The results obtained from the solid samples are compared to those obtained from aqueous solutions reported in the previous chapter. Dual fluorescence is reported for the anthroic acids and an explanation for this phenomenon is given.

ISBN

9780599474833

Pages

146

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