Synthesis of a triple-decker π-conjugated system to explore charge migration in organic semiconductors
Castaneda, Alma Delia
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Closely stacked π-systems exhibit physical properties that are a consequence of π- π interactions. The primary focus of this study is the production of a triple-decker π-conjugated system. Although many studies have investigated the use of para and meta-cyclophanes, research on ortho-cyclophanes in which arene rings are held in a stacked arrangement has been limited. This thesis describes a synthesis of the scaffold to hold conjugated units together. Ultimately, the stacked analog will be obtained by ketalization of a bicyclic ketone with ethylene glycol to lock the bicyclic core into a chair-chair conformation in which oligo(phenylene ethynylene)s are stacked atop one another. The optical properties of the stacked compound will be studied using UV-Vis and fluorescence spectroscopy. The electrochemical properties of the stacked compounds will be characterized using cyclic voltametry (CV) and differential pulse voltammetry (DPV).