A simple, straightforward [2+1] condensation of 5,6-diaryldipyrroethene dicarbinols with pyrrole under mild acid-catalyzed conditions resulted in the formation of highly desirable aromatic β-free meso-tetraaryl [14]triphyrins(2.1.1) in 15-18% yields. The triphyrins(2.1.1) are very novel monoanionic tridentate ligands that form metal complexes readily as demonstrated here by preparing Re(I) complexes.