Part 1. Discotic liquid crystals are a relatively new class of mesogens in which the molecules self assemble in the melt state to form highly ordered columnar stacks. The ability of the molecules to display this type of mesomorphic behavior is a function of their shape; a semi-rigid core with flexible "arms" gives the necessary flatness and broad diameter conducive to columnar stacking. We first set out to make discotic liquid crystals by synthesizing a series of three-armed aryloxy-s-triazines with aromatic Schiff's base moieties at the molecular periphery and investigate the thermal and optical behavior of these compounds. We discovered that these molecules were in fact rigid rod, or calamitic, liquid crystals based on the optical textures and X-ray diffraction patterns in the mesophase. This is in direct conflict with published but unsubstantiated reports of the "discotic” behavior of similar compounds. The failure of these compounds to give crystals suitable for X-ray crystal structural analysis prompted us to utilize electron microscopy to look at the microstructures formed when dilute solutions were evaporated onto different substrates. Surprisingly, these aryloxy-s-triazines in several different solvents formed well defined microtubules of varying dimensions on both copper and polymeric substrates. Hole diameters of up to 10³ Å and lengths of up to 0.5 cm were commonly seen using both transmission electron microscopy (TEM) and scanning electron microscopy (SEM). Finally, we understood via molecular modeling studies that the aryloxy-s-triazines adopted a rod shape in the mesophase due to the inherent flexibility of the ether linkages at the triazine core. By substituting 1,3,5-triphenylbenzene cores in place of the s-triazine we hoped to rigidify the molecules and prompt them to stack in a discotic or columnar fashion in the melt state. This plan was successful based on the X-ray diffraction patterns and optical textures observed with these compounds in the mesophase. Part 2. α-Aminonitriles and their derivatives have played an important role in the synthesis of enantiomerically pure and racemic α-amino acids for almost ninety years. Much less studied is the alkylation behavior of this particular class of compounds. The ability of the aminonitrile moiety to be deprotonated with a base and reacted with various electrophiles allows for the placement of carbonyl functionalities virtually anywhere in a synthetic system through hydrolysis of this aminonitrile group after alkylation. Using this "umpolung”, or reversed polarity, approach we have demonstrated the utility of this class of compounds by reacting them with several activated aromatic dihalides and aliphatic dihalides to produce high molecular weight poly(bis-α-aminonitrile)s which were in turn hydrolyzed under mild conditions to afford the corresponding polymeric ketones. This ability to form both wholly aromatic and mixed aliphatic/aromatic polyketones is extremely powerful and unprecedented in the literature to date. During the course of this research, it was also discovered that some of these α-aminonitriles underwent side reactions which were undesirable for polymerization but which produced interesting compounds in their own right. These enaminonitriles and quinodimethanes which resulted from dehydrocyanation were studied extensively in order to exploit the possible polymerization of these reactive intermediates. Finally, another route to ketones is through the reaction of enamines with appropriate electrophiles followed by acid hydrolysis. Research towards polymeric ketones was Carried out using monomeric di(enamine)s and aromatic diacid chlorides with the hope of producing high molecular weight polymeric 1,3-diketones. Unfortunately, the extent of reaction was not high enough to produce high molecular weight polymers. / Ph. D.