Synthesis of 10,20-substituted tetrabenzo-5,15-diazaporphyrin copper complexes from soluble precursors

Abstract

We report improved synthesis of the bicyclo[2.2.2]octadiene(BCOD)-fused 5,15-diazaporphyrin and meso-substituted derivatives by metal-template aza-annulation reaction. The obtained compounds act as the soluble precursors of tetrabenzo-5,15-diazaporphyrin (TBDAP) by thermal conversion. The substituents at meso-positions make significant differences in the optical properties and morphology in the thin film upon thermal conversion.