Non-covalent derivatives

• Online Access: http://hdl.handle.net/2047/D20194213

Non-covalent derivatization is a process by which one co-former molecules or more is incorporated into the solid-state matrix of the target molecule by way of non-covalent forces such as ionic Van der Waal forces, hydrogen bonding or pi-pi interactions. This incorporation produces a new material, a non-covalent derivative (NCD), which has properties that are distinctly different from those of the parent molecules. When faced with the need to modify the physical properties of a molecule, one would traditionally employ a series of familiar synthetic modifications. Examples of these modifications include halogenations for improved stability, oxidation for increased water-solubility, alkylations for lipophilic compatibility, or addition of double bonds for improved conjugation. In some cases, these (potentially) toxic, waste-producing and labor-intensive modifications can be replaced with non-covalent derivatization. The NCD, when compared to the parent molecules, can show dramatic changes in thermal properties, solubility, optical properties and stability while maintaining the desirable properties of the target molecule. This dissertation explores several specific, practical applications of NCDs. A study is presented that demonstrates the capacity of NCDs to impart oxidative stability to solid-state materials. This capacity has far-reaching applications in a diversity of specialty chemical areas where shelf-stability and product performance are vital. Two case studies are presented that explore the application of NCDs for product development. In the first case, the color formation of a biomimetic hair dye is altered by the use of an NCD. In the second, a peroxyacid is stabilized in water by way of an NCD. These three studies demonstrate the utility and versatility of non-covalent derivatization as a tool in material development and optimization.