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Published on: November 22, 2015
Synthesis of polyphenylene dendrimers related to "cubic graphite"
Xianfeng Shen1, Douglas M Ho, Robert A Pascal
1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
Abstract:
Four large, 6-fold symmetric, polyphenylene hydrocarbons have been prepared by short syntheses that chiefly employed alkyne trimerization, palladium-catalyzed coupling, and Diels-Alder reactions. The two largest of these molecules, hexakis[4'-(pentaphenylphenyl)biphenyl-4-yl]benzene (4, C(294)H(198)) and hexakis[4'-(2,3,4,5-tetraphenylphenyl)biphenyl-4-yl]benzene (5, C(258)H(174)) are substructures of "phenylogous cubic graphite", and the other two, hexakis(2',3',4',5',6'-pentaphenylbiphenyl-4-yl)benzene (26, C(258)H(174)) and hexakis(2',3',4',5'-tetraphenylbiphenyl-4-yl)benzene (25, C(222)H(150)) are strongly pitched, six-bladed molecular propellers. The X-ray crystal structure of compound 26 has also been determined; dendrimer 26 is at present the largest crystallographically characterized hydrocarbon.
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