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      Highly Regioselective Domino Benzannulation Reaction of Buta-1,3-diynes To Construct Irregular Nanographenes

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          Aromatic molecular-bowl hydrocarbons: synthetic derivatives, their structures, and physical properties.

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            Geodesic polyarenes by flash vacuum pyrolysis.

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              A grossly warped nanographene and the consequences of multiple odd-membered-ring defects.

              Graphite, the most stable form of elemental carbon, consists of pure carbon sheets stacked upon one another like reams of paper. Individual sheets, known as graphene, prefer planar geometries as a consequence of the hexagonal honeycomb-like arrangements of trigonal carbon atoms that comprise their two-dimensional networks. Defects in the form of non-hexagonal rings in such networks cause distortions away from planarity. Herein we report an extreme example of this phenomenon. A 26-ring C80H30 nanographene that incorporates five seven-membered rings and one five-membered ring embedded in a hexagonal lattice was synthesized by stepwise chemical methods, isolated, purified and fully characterized spectroscopically. Its grossly warped structure was revealed by single-crystal X-ray crystallography. An independent synthetic route to a freely soluble derivative of this new type of 'nanocarbon' is also reported. Experimental data reveal how the properties of such a large graphene subunit are affected by multiple odd-membered-ring defects.
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                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley
                14337851
                November 05 2018
                November 05 2018
                September 11 2018
                : 57
                : 45
                : 14773-14777
                Affiliations
                [1 ]Department of Chemistry; University of Nevada, Reno; 1664 N. Virginia St. Reno NV 89557 USA
                Article
                10.1002/anie.201808043
                586cf8ca-e1f1-4ec3-8b46-3872af6c594f
                © 2018

                http://doi.wiley.com/10.1002/tdm_license_1.1

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