Self-assembled metallocomplexes are dynamic molecules with cavities that are capable of encapsulating a wide range of guests.  Examples include a large cubic metallocomplex self-assembled from iron(II), pyridinecarbaldehyde, and square planar tetraamino-phenylporphyrin, which were found to reversibly encapsulate large molecules like C<sub>60</sub>. Unfortunately, these metallocubes have low solubility in most solvents.  In this presentation we will discuss progress toward the synthesis of cubic metallocomplexes that should have high solubility in aqueous and organic solvents. This goal will be achieved by adding pendant polyethylene glycol (PEG) chains to the molecular cubes using the well-establish “Click Chemistry” methodology.  Sodium azide was reacted with diethylene glycol monomethyl ether to produce a PEGylated azide in 99% yield. Tetraethynylpyridyl porphyrin was synthesized via a Sonogashira coupling of TMS-acetylene and 2-bromo-pyridine-5-carbaldehyde (70%), followed by reaction with pyrrole.  The TMS protecting group will be removed with TBAF and the resulting alkyne can undergo cycloaddition with the PEGylated azide using a Cu catalyst to give the ligand needed for self-assembly of the metallocubes.

Synthesis of water-soluble cubic metallocomplexes

251st National Meeting (2016)

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