Phenothiazinophanes:: Synthesis, structure, and intramolecular electronic communication

Ortho-phenylene, ethenylene, and ethylene-bridged phenothiazinophanes are synthesized by Suzuki coupling or McMurry dimerization and catalytic hydrogenation at ambient pressure. Intensive intramolecular electronic communication of the phenothiazinyl subunits is found according to cyclic voltammetry. In addition, the macrocycles display blue to green fluorescence with large Stokes shifts. In the solid state, the cyclophanes are arranged in unidimensional stacks. This orientation appears to be favorable for anisotropic charge transport in hole-transport materials for organic field effect transistors (OFET) applications.