Multi-Step Organic Synthesis of Octaaminotetraphenylene Hydrochloride For Potential Use in Material Chemistry

Undergraduate Honors Thesis

Citations

Citeable URL: https://scholar.colorado.edu/concern/undergraduate_honors_theses/z316q341k

Abstract

Conductive metal-organic frameworks (c-MOFs) represent a class of porous semiconducting materials that hold significant promise for a wide range of applications, including electrocatalysis, sensing, and energy storage.11 However, the majority of reported c-MOFs are confined to two-dimensional (2D) structures, leaving their three-dimensional (3D) counterparts largely unexplored. Among the potential ligands suitable for the construction of 3D c-MOFs and other conductive polymers, octaaminotetraphenylene (OATP) stands out due to its unique saddle-shaped molecular structure and amino chelating groups. Despite its potential, the synthesis of OATP has suffered from low yields and has never been employed in material chemistry. OATP can be synthesized through a four-step process that involves building a tetraphenylene backbone from 4-iodobiphenylene, subsequent bromination, amination, then finally hydrolysis to yield the desired ligand.3 In this experiment, the reported synthetic route for OATP was validated, and each step of the reaction was optimized to achieve a higher overall yield.

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