Ligands for the development of metallomesogens (metal-containing-liquid-crystals) have attracted attention due to potential applications in materials science, such as optical devices, magnetic switches, and conductors. Our group has targeted compounds of bis(3-alkoxy)pyridine amines as potential ligands for metal complexes due to the well-documented complexes of pyridine derivatives with transition metals (Cu2+, Mn2+, Co2+). Furthermore, these targets are expected to form radical cations as their phenyl amine counterparts. Our group has synthesized 16- and 10- carbon chain analogs of bis(3-alkoxy)pyridine amines. Here we present our attempts to synthesize these targets with copper and palladium catalysts from 1-alkoxy-3-halobenzene derivatives. Attempts to synthesize these targets under copper-catalyzed conditions, aromatic and non-aromatic solvents with different bases, were not successful thus leading to the recovery of starting material. We have determined that amine coupling using halobenzene derivatives of 10- and 16- carbon chains is effectively achieved under palladium-catalyzed conditions, while copper as the catalyst yields no product.

Towards the synthesis of pyridine-based ligands as potential organometallic magnetic liquid crystals

243rd National Meeting (2012)

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