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Long-Proposed Porphyrin Is Finally Made

Near-infrared absorber may find use optics applications

by Sarah Everts
December 20, 2010 | A version of this story appeared in Volume 88, Issue 51

Chemists at Oxford University have finally found a way to synthesize a long-sought-after porphyrin with four anthracene units on its periphery. More than 35 years ago, the late Teh Fu Yen of the University of Southern California proposed making such a molecule, expecting that its properties would be useful in electronic devices, says Oxford chemistry professor Harry L. Anderson. Anderson worked with Nicola K. S. Davis and Amber L. Thompson to finally assemble and crystallize the fused tetraanthracenylporphyrin by oxidizing a meso-anthracenyl nickel porphyrin with iron chloride ( J. Am. Chem. Soc.10.1021/ja109671f). The molecule absorbs strongly in the near-infrared region (1,417 nm), which is unusual for organic compounds. “The near-infrared wavelength region (800–1,600 nm) is important for many applications such as fiber-optic communications and night vision, so it is important to have dyes that operate in this spectral region,” Anderson says. Furthermore, the crystal structure reveals that the decorated porphyrin forms tight π-stacked dimers, which could be turned into flat “molecular graphenes” that are useful in organic semiconductors and nonlinear optical dyes—if the compound lost its bulky side chains.


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