Porphyrins substituted with antioxidant 2,6-di-tert-butylphenol substituents have been shown to exhibit different conformations based on the oxidation state of those substituents leading to the oxoporphyrinogens.^1,2 We have attempted to apply this feature in numerous other macrocyclic and non-macrocyclic chromophores in order to assess any possibility for controlling molecular morphology. These attempts have included phthalocyanines, triarylamines (TPA), hexaphenylbenzene (HPB) and resorcinarene. Here, we will describe the results of these investigations including highlighting the potential applications of different compounds obtained from the porphyrin system,^3,4 synthesis and structure in the phthalocyanine,⁵ TPA and HPB systems,⁶ and an extensive crystallographic analysis of the resorcinarene system.⁷ We will also present spectroscopic aspects of these compounds including how they interact with some analytes, and electrochemical data illustrating coupling between structures and the oxidation states of the compounds.

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Figure. X-ray crystal structure of antioxidant-substituted resorcinarene.