An antiaromatic porphyrin complex: tetraphenylporphyrinato(silicon)(L)2 (L=THF or pyridine) |
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Authors: | Cissell Julie A Vaid Thomas P Rheingold Arnold L |
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Institution: | Center for Materials Innovation and Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA. |
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Abstract: | Treatment of Si(TPP)Cl2 (TPP = tetraphenylporphyrinato) with 2 equiv of Na/Hg in THF yields the reduced porphyrin complex, Si(TPP)(THF)2, in which the porphyrin ring system has an oxidation state of 4- and the complex is antiaromatic. Single-crystal X-ray diffraction reveals that Si(TPP)(THF)2 is highly ruffled and exhibits a unique C-C bond length alternation around its periphery. In addition, experimental 1H and 29Si NMR chemical shifts and NICS (nucleus-independent chemical shift) calculations on a model compound indicate a strong paratropic ring current in Si(TPP). |
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