18, 18′-Dihexyl [9, 9′] biphenanthro [9, 10-b] triphenylene: Construction and Consequences of a Profoundly Hindered Aryl− Aryl Single Bond

CL Hilton, JM Crowfoot, P Rempala…

Index: Hilton, Cameron L.; Crowfoot, Jeremy M.; Rempala, Pawel; King, Benjamin T. Journal of the American Chemical Society, 2008 , vol. 130, # 40 p. 13392 - 13399

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Citation Number: 18

Abstract

The title compound, 1-Hex, was synthesized by the Zr-mediated biphenylation of 4, 4′- dihexyloctabromobiphenyl using (Li (THF) 4) 2· Zr (biphe) 3, where biphe is the 2, 2′- biphenyldiyl ligand, in 5% isolated yield. Two independent X-ray diffraction analyses revealed that arene 1-Hex possesses a highly strained and hindered aryl− aryl single bond. This bond causes the phenanthro [9, 10-b] triphenylene (PTP) moieties to twist ( ...