Porphyrins are highly interesting compounds with potential applications in a wide range of fields, including light-energy conversion, fluorescence switches, fluorescent sensors, organic light-emitting diode (OLED) devices, photodynamic therapy (PDT), third-order non-linear optical materials and molecular wires. Cationic ?6-chloroarene-?5-cyclopentadienyliron(II) complexes containing novel porphyrin and metalloporphyrin dendrimers were synthesized and their spectroscopic properties were studied. Divergent approaches were applied to give highly symmetrical branched dendritic compounds. Metal-mediated nucleophilic aromatic substitution and Steglich esterification were used to prepare these dendrimers. Furthermore, the synthesis and spectroscopic properties of a series of porphyrin-based polymers prepared via condensation polymerization of disubstituted porphyrins with cationic ?6-chloroarene-?5-cyclopentadienyliron(II) complexes will be described.  The incorporation of cationic ?6-chloroarene-?5-cyclopentadienyliron moieties into both polymer and dendritic systems enhance solubility, and also facilitate the synthetic nucleophilic aromatic substitution, addition and condensation reactions, due to the intense electron-withdrawing ability of the iron center. This incorportation resulted in improved polymerization and dendrimer formation reactions, with greatly reduced reaction times in mild conditions. In addition, demetallation of the resulting polymers and dendrimers by photolysis resulted in the formation of novel, entirely organic materials, with unique structures, properties, and applications. For example, the linear polyether porphyrin polymers prepared in this way have potential applications in the purification of natural waters, due to their selective coordination with heavy metals. The spectroscopic properties of the porphyrin polymers, dendrimers and their precursors have been characterized using nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), ultraviolet-visible absorption and fluorescence spectroscopy. Redox and conductivity studies of these materials will also be discussed.

Synthesis and spectroscopic studies of organoiron complexes containing novel porphyrin dendrimers and polymers

248th National Meeting (2014)

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