Fusing Together Perylene Bisimides with Arene Cores

Significance

The authors report on the photochemically induced iodocyclization on a bis-(perylene bisimide) scaffold. Utilizing the soluble perylene ester precursor 1 and a catalytic amount of iodine in sunlight, the corresponding fused aromatic structure 2 could be formed in high yield. At higher temperatures the linear product 3 could also be prepared. Only minor amounts of the other constitutional isomer were observed in both cases. Conversion of each of these compounds into the bisimides 4 and 5 occurred in near quantitative yields. Additionally, symmetrically fused perylene bisimides with fluorenyl and dithiophenyl cores were also efficiently synthesized in this manner.