Metal – organic polyhedra (MOPs) are 3 –D structures consisting of organic ligands as the edges or faces and metal ions as the corners, able to encapsulate molecules and be hosts to a myriad of chemical reactions. Meso – tetrasubstituted porphyrins are large, aromatic macrocycles shaped like squares with substituents at the corners suggesting they would be useful for forming the faces of MOPs. The goal of this research is to synthesize four meso – tetrasubstituted porphyrins which would be used to form porphyrin – walled MOPs. Tetrakis (3 – pyridyl) porphyrin (3PP), tetrakis (2 – pyridyl) porphyrin (2PP) and tetrakis (2, 3 – dimethoxy) porphyrin (2, 3 – diOMeP) have been synthesized and purified, and synthesis of tetrakis (3,4 – dimethoxy) porphyrin (3, 4 – diOMeP) is underway. In the case of the latter two products, the methoxy groups will be removed to yield tetrakis (2, 3 – dihydroxy) porphyrin (2, 3 – diOHP) and tetrakis (3, 4 – dihydroxy) porphyrin (3, 4 – diOHP). These tetrasubstituted porphyrins were chosen because of their ability to act as exo-dentate ligands, meaning they can bind to a metal on the four “corners” of the porphyrin exterior. Several attempts at self – assembly of 3PP with metal salts have been made with varying metals, anions, reacting and precipitating solvents and reaction conditions. One result yielding crystals suitable for X – Ray crystallography was obtained and the structure will be presented. Although not an MOP, the structure shows promise for future isolation of porphyrin – walled MOPs.

Metal – organic assemblies of meso – tetrasubstituted porphyrins

249th National Meeting (2015)

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