3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF 2 Complex.

3,6-Carbazole precursors were used to prepare an octaphyrin. The conformation and electronic structure of the system could be modulated through trifluoroacetate (TFA) protonation and BF 2 complexation. The resulting nonaromatic macrocyclic complexes, 2-2TFA and 2-2BF 2 , displayed noteworthy photophysical properties. For instance, the diprotonated species 2-2TFA showed a strong panchromic absorption up to 800 nm, while the bis-BF 2 -chelated dipyrromethene (BODIPY)-like complex 2-2BF 2 exhibited an intense visible absorption feature (ε 535nm = 2.1 × 10 5 M -1 cm -1 ), as well as a relatively red-shifted emission at 640 nm characterized by a large Stokes shift. It was found that 2-2BF 2 could be used to construct a high-quality organic microlaser that functions under optical pumping. The present study highlights the potential utility of expanded porphyrins as possible laser dyes.