Abstract
AbstractSix variably functionalized phenanthrene‐based bis(catechol) derivatives have been synthesized and their ability to undergo dynamic covalent assembly with 1,4‐benzenediboronic acid (BDBA) to give discrete, shape‐persistent [2+2] assemblies has been investigated. Systematically varying the functionality of the bis(catechol) derivatives is found to influence both the reaction conditions necessary to promote their self‐assembly with BDBA as well as the stability of the resulting assemblies in the presence of protic solvents. A model is proposed to describe how solvent choice and starting material functionality must be carefully balanced in order to shift many competing equilibria toward the formation of discrete, soluble covalent organic polygons. The results are expected to provide additional insight into optimizing the synthesis of other boronate ester polygons/polyhedra as well as related, “infinite” covalent organic frameworks (COFs).
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