o-Arene-connected porphyrinoids were synthesized with o-(2-thienyl)vinylarene motif as a new building block for porphyrinoids. This motif can replace meso-aryl-substituted dipyrromethene and serve as a command key arranging o-connectivity of porphyrinoid. While 6a (benzene version) is very weak, 6b (pyridine version) shows a substantial amount of diatropic ring current due to reduced steric hindrance (without H23) and rigidified Pd-6a became more aromatic than 6b.