The properties of porphyrinoids are substantially affected by their skeleton and structural factors. In particular, inclusion of heteroatoms into the p-conjugation circuit of porphyrinoids induces dramatic change of their electronic structures. Recently, 10-heterocorroles has regained the spotlight as promising candidates for novel building blocks of molecular materials as electronically tunable porphyrin analogues.

We have explored the synthesis and properties of meso-aryl type 10-aza-, 10-oxa-, 10-thia-, and 10-silacorroles. These 10-heterocorroles can be efficiently prepared fro bis(dipyrrin) metal complexes as precursors. Optical and electrochemical properties of these compounds are heavily dependent on the introduced heteroatoms at the meso-positions. The energy level of HOMOs and LUMOs of these molecules can be effectively manipulated by the proper choice of the heteroatoms.