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Synfacts 2010(10): 1128-1128  
DOI: 10.1055/s-0030-1258638
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Soluble Fused Pyrene-Diporphyrins via Oxidative Ring Closure

Contributor(s): Timothy M. Swager, Olesya Haze
V. V. Diev, K. Hanson, J. D. Zimmerman, S. R. Forrest, M. E. Thompson*
University of Southern California, Los Angeles and University of Michigan, Ann Arbor, USA
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Publication History

Publication Date:
22 September 2010 (online)

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Significance

Pyrene-diporphyrin hybrids with NIR absorption bands are reported. The standard Suzuki coupling and Osuka’s oxidative fusion of porphyrin rings are followed by an elegant oxidative ring closure resulting in a double fusion of the non-activated pyrenes. Pyrene-(β,meso)-fused diporphyrins 2 are not planar, and this secures good yields and solubility in organic solvents. Dual action of the pyrenes and the Pb²+ results in an extreme red shift in the absorption spectrum of 2c, which extends to 1.53 µm (λmax = 1459 nm) in solution and 1.9 µm (λmax = 1527 nm) in thin film.