Synthesis of meso-substituted subphthalocyanine-subporphyrin hybrids: boron subtribenzodiazaporphyrins.

The first syntheses of hybrid structures that lie between subphthalocyanines and subporphyrins are reported. The versatile single-step synthetic method uses a preformed aminoisoindolene to provide the bridging methine unit and its substituent while trialkoxyborates simultaneously act as Lewis acid, template, and provider of the apical substituent. The selection of each component therefore allows for the controlled formation of diverse, differentially functionalized systems. The new hybrids are isolated as robust, pure materials that display intense absorption and emission in the mid-visible region. The new compounds are further characterized in solution and solid state by variable-temperature NMR spectroscopy and X-ray crystallography, respectively.