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. Benzodipyrenes (BDPs) were synthesized through a four‐fold alkyne benzannulation reaction in good yields. The BDP products exhibit good relative photostabilities with half‐lives up to 4612 min in THF.