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.