Aromatization-Based Methodology in the Synthesis of Designed and Naturally Occurring Pi Systems with Unusual Structures and Useful Properties

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The overarching objective of the proposed research is to exploit methodology in the field of organic synthesis that has been developed in my group to design and synthesize polycyclic aromatic and heteroaromatic compounds with unusual structures and/or potentially useful properties. The synthesis of molecules with unusual structures is challenging because such systems are necessarily high in energy. The methodology used by my group to generate energetically unfavourable (and therefore very interesting and potentially useful) molecules owes its success to reactions that result in the formation of one or more "aromatic" rings. These energetically advantageous processes offset the disadvantages of forming distorted structures. Bending and battering molecules into shapes that deviate from ideal parameters in a systematic fashion provides an opportunity to learn about the relationships between changes in structure and changes in properties. This knowledge may then be used to design molecules with tailored properties, which may prove to be useful for a variety of applications, include sensors and optoelectronic devices.