The synthesis of selenium and tellurium core-modified carbaporphyrinogens was carried out by the reaction of functional selenophene/tellurophene diols with azulene or a benzitripyrrane in the presence of acid. The products were obtained in moderate yields and were characterized by using H-1 and C-13 NMR, UV-vis, FT-IR, CV, and HRMS spectroscopic techniques. Further, oxidation of the obtained core-modified carbaporphyrinogens in the presence of DDQ in CHCl3 afforded the corresponding carbaporphyrins in good yields. Benziporphyrins showed no indication of a ring current or macrocyclic aromaticity as confirmed by using proton NMR spectroscopy, but the addition of TFA gave rise to the formation of weakly diatropic dications.