Department of Chemistry
Master of Science
Cyclophanes are macromolecules that are known to effectively bind with molecules to form host-guest complexes. Several cyclophane molecules, referred to as corrals (1-6) by their founders, have been synthesized. The characterization of these compounds and their complexes has been investigated using combined spectroscopic and theoretical methods. Hostguest interactions of cyclophane-anthracene (C-A), cyclophane-9-fluorenone (C-F) and cyclophane-pyrene (C-P) complex systems in dichloromethane are presented in this thesis. The stability constants, log Ka, for the C-A, C-F and C-P complexes are determined using absorption and fluorescence spectroscopy. Heats of formation of corral 2 complexes were determined by measuring the complex association constants at 25, 29 and 32 °C. Results reveal that binding of the non-polar guests by the cyclophane molecules are thermodynamically favored over binding with polar guest. Computational studies indicate difference in energy due to solvent effect of the complexes in the condensed phase. Excited state lifetimes of these systems are also determined, and they support fluorescence as a path of relaxing back to the ground state.
O'Brien, Mark, "Spectroscopic Studies of Inclusion Host-Guest Complexes Between Cyclophane Corrals and Polcyclic Aromatic Hydrocarbons" (2005). Masters Theses & Specialist Projects. Paper 470.