title: A grossly warped nanographene and the consequences of multiple odd-membered-ring defects.
abstract: 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.
authors: Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
authors: Katsuaki
authors: K
authors: Kawasumi
authors: Qianyan
authors: Q
authors: Zhang
authors: Yasutomo
authors: Y
authors: Segawa
authors: Lawrence T
authors: LT
authors: Scott
authors: Kenichiro
authors: K
authors: Itami
mesh_terms: D018360:Crystallography, X-Ray; D006108:Graphite / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D049329:Nanostructures / Q000737:chemistry*
chemical_list: D006108:Graphite
references: J Am Chem Soc. 2012 Aug 1;134(30):12442-5
references: 22800512
references: Chem Rev. 2006 Dec;106(12):4843-67
references: 17165677
references: Acc Chem Res. 2012 Aug 21;45(8):1378-89
references: 22587963
references: Chem Rev. 2006 Dec;106(12):4868-84
references: 17165678
references: Chem Commun (Camb). 2012 Sep 14;48(71):8880-2
references: 22810270
references: Angew Chem Int Ed Engl. 2009;48(33):6112-6
references: 19588479
references: J Org Chem. 2013 Mar 15;78(6):2266-74
references: 23374076
references: J Am Chem Soc. 2011 Jun 1;133(21):8354-61
references: 21542589
references: J Am Chem Soc. 2011 Jul 20;133(28):10716-9
references: 21699210
references: J Am Chem Soc. 2012 Feb 15;134(6):2962-5
references: 22296245
references: Science. 2002 Feb 22;295(5559):1500-3
references: 11859187
references: J Phys Chem B. 2009 Feb 19;113(7):1954-62
references: 19173564
references: J Am Chem Soc. 2012 Jan 11;134(1):107-10
references: 22133011
references: Science. 2004 Oct 22;306(5696):666-9
references: 15499015
references: Angew Chem Int Ed Engl. 2012 Sep 3;51(36):8960-9009
references: 22887739
references: Angew Chem Int Ed Engl. 2010;49(2):399-402
references: 19957259
references: Angew Chem Int Ed Engl. 2010 Dec 27;49(52):10202-5
references: 21105035
references: J Am Chem Soc. 2008 Dec 31;130(52):17646-7
references: 19055403
references: J Org Chem. 2012 Dec 7;77(23):10473-8
references: 23126565
references: Nat Chem. 2013 Jul;5(7):572-6
references: 23787746
references: Chem Rev. 2001 May;101(5):1267-300
references: 11710221
references: Chemistry. 2012 Dec 21;18(52):16621-5
references: 23224990
references: Angew Chem Int Ed Engl. 2009;48(28):5094-115
references: 19557755
references: J Am Chem Soc. 2001 Jan 31;123(4):517-25
references: 11456563
references: J Org Chem. 2012 Jan 6;77(1):311-6
references: 22129364
references: J Am Chem Soc. 2012 Sep 26;134(38):15664-7
references: 22978569
references: Angew Chem Int Ed Engl. 2012 Jul 27;51(31):7640-54
references: 22777811
references: J Am Chem Soc. 2012 Sep 19;134(37):15169-72
references: 22946784