Synthesis, Structure, Photophysical Properties, and Photostability of Benzodipyrenes.

This work explores the syntheses, structures, photophysical properties, and photostability of benzodipyrenes (BDPs). BDPs were synthesized through an InCl3 -AgNTf2 -catalyzed, four-fold alkyne benzannulation reaction. The structures of BDP 4 a and its corresponding endoperoxide product were unambiguously confirmed by X-ray crystallography. The BDPs reported here can also be recognized as peri- and cata-benzannulated pentacenes with a non-functionalized central ring. Unlike the previous reported pentacene-based polycyclic aromatic hydrocarbons, the absorbances of the BDPs were blueshifted by ca. 40 nm relative to pentacene, even after extension of π-conjugation. The newly synthesized BDP products exhibit relatively good stability with half-lives as high as 4612 min in THF.