Metallocomplexes are dynamic molecules with cavities that are capable of encapsulating a wide range of guests. In the presence of iron(II) and pyridyl aldehyde, square planar tetraaminophenyl porphyrins spontaneously self-assemble into cubic metallocomplexes, which can encapsulate molecules like C60. Unfortunately, these metallocubes have low solubility in most solvents. The purpose of this research is to synthesize cubic iron metallocomplexes with high solubility in aqueous and organic solvents. This can be achieved by adding pendant polyethylene glycol (PEG) chains onto the porphyrin subcomponent. Diethylene glycol monomethyl ether was tosylated and reacted with sodium azide to produce a PEGylated azide (1) in 99% yield. 6-((Trimethylsilyl)ethynyl)-3-formyl-pyridine (2), was synthesized from 6-bromo-3-pyridinecarboxaldehyde and ethynyltrimethylsilane in 70% yield. Compounds 1 and 2 were then coupled in the presence of copper sulfate, sodium ascorbate, and potassium carbonate to give a PEGylated triazole pyridine aldehyde (3) in 62% yield. This aldehyde was reacted with pyrrole in acetic acid to produce 5,10,15,20-tetrakis-(4-(4-formyl-2-pyridyl)-1-(ethyl-2-(2-methoxyethoxy)1H-1,2,3-triazole) porphyrin (4) in a 15% yield. The cubic metallocages will be self-assembled from the PEGylated porphyrin 4 and iron triflate.

Synthesis of a water-soluble cubic porphyrin-based metallocomplex via click-chemistry

253rd National Meeting (2017)

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