3,6-Carbazoylene Octaphyrin (1.0.0.0.1.0.0.0) and Its Bis-BF2 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 BF2 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-BF2-chelated dipyrromethene (BODIPY)-like complex 2-2BF(2) exhibited an intense visible absorption feature (epsilon(535nm) = 2.1 x 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.