Crystalline Hybrid Polyphenylene Macromolecules from Octaalkynylsilsesquioxanes, Crystal Structures, and a Potential Route to 3-D Graphenes Mark F. Roll Jeffrey W. Kampf Richard M. Laine 10.1021/ma200081q.s001 https://acs.figshare.com/articles/journal_contribution/Crystalline_Hybrid_Polyphenylene_Macromolecules_from_Octaalkynylsilsesquioxanes_Crystal_Structures_and_a_Potential_Route_to_3_D_Graphenes/2654770 We report here the Diels−Alder reaction of octa(diphenylacetylene)silsesquioxane [DPA<sub>8</sub>OS] with tetraphenylcyclopentadienone or tetra(<i>p</i>-tolyl)cyclopentadienone to form octa(hexaphenylbenzene)octasilsesquioxane, (Ph<sub>6</sub>C<sub>6</sub>)<sub>8</sub>OS, or octa(tetratolyldiphenylbenzene)octasilsesquioxane, (<i>p</i>-Tolyl<sub>4</sub>Ph<sub>2</sub>C<sub>6</sub>)<sub>8</sub>OS. Likewise, tetra(<i>p</i>-tolyl)cyclopentadienone reacts with octa(<i>p</i>-tolylethynylphenyl)OS to form octa(pentatolylphenylbenzene)octasilsesquioxane (<i>p</i>-Tolyl<sub>5</sub>PhC<sub>6</sub>)<sub>8</sub>OS. These compounds, with molecular weights of 4685−5245 Da, were isolated and characterized using a variety of analytical methods. The crystal structure of DPA<sub>8</sub>OS offers a 3 nm<sup>3</sup> unit cell with <i>Z</i> = 1. The crystal structure of (Ph<sub>6</sub>C<sub>6</sub>)<sub>8</sub>OS was determined to have a triclinic unit cell of 11 nm<sup>3</sup> with <i>Z</i> = 1. The latter structure is believed to be the largest discrete molecular structure reported with 330 carbons. Efforts to dehydrogenatively cyclize (Scholl reaction) the hexaarylbenzene groups to form 3-D octgraphene compounds are described. 2011-05-10 00:00:00 crystal structure triclinic unit cell Crystalline Hybrid Polyphenylene Macromolecules 3 nm 3 unit cell DPA 8OS compound octa tetra Ph 6C 11 nm 3 1.