Synthesis of Functionalized Perfluorinated Porphyrins for Improved Spin Switching

We have established a method to synthesize perfluorinated meso-phenylporphyrins with one phenyl group bearing a substituent in the ortho position. These novel electron-deficient porphyrins are interesting for model enzymes, catalysis, photodynamic therapy, and electron transfer. The key step is the synthesis of an iodine-substituted porphyrin and its Suzuki cross coupling with boronic acid derivatives. We applied the novel strategy to synthesize a highly electron-deficient, azopyridine-substituted Ni–porphyrin that undergoes an improved ligand-driven coordination-induced spin-state switch.