I. Physical organic studies of an interfacial Diels-Alder reaction. II. A chemoselective approach to gold nanoparticles assembly and polymeric multilayer deposition on solid supports

Our research effort has been focused on the surface chemistry approach to develop new methodology for the selective coupling of soluble molecules with ligands immobilized on the surface. Because of the selectivity nature, these coupling reagents can usually react with one another even in the presence of diverse functional groups. The two such reactions namely the Diels-Alder reaction and chemoselective ligation reaction are known to provide selective and covalent coupling in solution chemistry. It would be logical to utilize these reactions to selectively couple a variety of molecules and reagents to the surface. However, in order to fully explore the potentials of these coupling reactions, it is important to first understand their chemical and kinetic behavior at the interface.; This dissertation will emphasize on the mechanistic studies and some applications of the Diels-Alder reaction and chemoselective ligation. Chapter two introduces the use of monolayer presenting quinone groups to probe the effect of solvent on the kinetics of interfacial Diels-Alder reaction by electrochemistry. Chapter three describes the use of quinone monolayer to study the background effect on the Diels-Alder reaction mechanism on the surface. Chapter four describes the use of chemoselective ligation between aminooxy and ketone groups to immobilize gold nanoparticles onto SAMs coated gold substrate. Finally, chapter five extends this chemoselective approach to develop a methodology for multilayer deposition of conjugated polymers on solid supports.