Synfacts 2010(7): 0772-0772  
DOI: 10.1055/s-0029-1220060
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Fusing Together Perylene Bisimides with Arene Cores

Contributor(s): Timothy M. Swager, William R. Collins
Z. Yuan, Y. Xiao*, X. Qian*
Dalian University of Technology and East China University of Science and Technology, Shanghai, P. R. of China
Further Information

Publication History

Publication Date:
22 June 2010 (online)

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.