Planar conjugated compounds are becoming an increasingly interesting field of research due to their possible applications as highly fluorescent molecules and dyes, as well as molecular devices and machines. This project aims to synthesize pi-expanded coumarin containing molecules that adopt a propeller-like geometry and can be adequately characterized. This geometry includes a 1,3,5-triphenylbenzene core with three lactone bridges to force rigidity, and therefore planarity, in the structures. Previous work in our lab has shown the ability of simpler linear versions of these molecules to act as molecular geometry switches of aryl-aryl dihedral angles. One challenge with synthesizing the proposed propeller-type molecules is that they are difficult to solubilize due to pi-aggregation and therefore can be difficult to study. The objective of this specific project is to synthesize a propeller molecule that has both a planar conformation and is adequately soluble for characterization techniques. Once the molecule has been synthesized, it will be subjected to pH-driven conformational change reactions in order to test the molecule’s ability to reversibly transition from its planar to non-planar states. These changes occur through the breaking and reformation of the lactone bridges and can be readily monitored through NMR spectroscopy and absorption and emission of UV light.<br/>

Propeller-shaped Pi-expanded coumarins as aryl-aryl dihedral angle switches

255th National Meeting (2018)

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