Date of Award
Bachelor of Science
2-Acetonaphthone (2-AN) is an unusual molecule in that it will only fluoresce in the presence ot strong hydrogen bond donors such as water. Less than a 10 mol % addition of a weaker hydrogen bonding molecule such as ethanol results in significant quenching of the 2-AN fluorescence in water. We have used this behavior to monitor the binding of 2-AN to the ethanol-like interior of the α-, β-, and y-Cyclodextrin (CD) C2'1ities. The addition of CO's to aqueous solutions of 2-AN causes a dramatic quenching of the 2-AN fluorescence. Because the quenching is static, we attribute the observed behavior to the formation of a temperature dependent equilibrium between the CD, 2-AN and their corresponding 1:1 complex. The equilibrium constant (K) can be determined by fluorescence quenching measurements. We have obtained data which characterizes the temperature dependency of the formation constant and used it to calculate the enthalpies and entropies of complex formation. Further studies involving the use of fluorinated alcohols to modify the cyclodextrin cavity as well as methods for the analysis of complexes with other than 1:1 stoichiometries will be discussed.
Fraiji, Elie K. Jr, "The use of fluorescence quenching measurements to study the cyclodextrin inclusion complexes of 2-aceotonaphthone" (1990). Honors Theses. 2028.