Meso‐Monoaryl‐Substituted Neo‐confused Calixsmaragdyrins and Meso‐monoaryl Substituted Smaragdyrins: Synthesis, Structures and Properties

Abstract While S N Ar reaction of 3,5‐dibromo‐8‐mesityl BODIPY 1 with a 5,10‐diaryltripyrrane with Cs 2 CO 3 was reported to provide 5,10,19‐triaryl[22]smaragdyrin as the first synthetic method of all‐aza smaragdyrin, the reaction of 1 with meso ‐free tripyrrane 6 took a different course to give a doubly Neo‐confused calixsmaragdyrin 7 . On the other hand, the S N Ar reaction of 2,3,5,6‐tetrabromo‐8‐mesityl BODIPY 9 with 6 provided 16,22‐dibromo‐19‐mesitylsmaragdyrin BF 2 complex 10 . In addition, calixsmaragdyirn 7 has been shown to serve as a ligand for Rh I and B III metals, and oxidation of 10 with MnO 2 gave meso ‐oxidized smaragdyrin 11 that was shown to be weakly antiaromatic.