Bromination of graphene with pentagonal, hexagonal zigzag and armchair, and heptagonal edges
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The bromination reactivity of azulene, naphthalene, and graphene with pentagonal, hexagonal zigzag and armchair, and heptagonal edges was theoretically estimated by density functional theory calculation and experimentally clarified by analyzing bromination of azulene and naphthalene using gas chromatography–mass spectrometry and ultraviolet–visible spectroscopy. The experimental and theoretical bromination reactivity of azulene with one pentagon and one heptagon was higher than that of naphthalene with two hexagons because of electron-rich carbon atoms on the pentagon. On the other hand, the tendency of theoretical bromination reactivity of pentagonal, hexagonal, and heptagonal edges on graphene was totally opposite to that on azulene and naphthalene. The order of the bromination reactivity of graphene edges was hexagonal zigzag > pentagonal > heptagonal and hexagonal armchair edges. The highest reactivity of hexagonal zigzag edges can be explained by the largest amount of electrons of carbon atoms among all of edges of graphene.
KeywordsNaphthalene Density Functional Theory Calculation Azulene Graphene Edge Zigzag Edge
This work was supported by Japan Interaction in Science and Technology Forum.
- 11.Harris PJF, Liu Z, Suenaga K (2008) Imaging the atomic structure of activated carbon. J Phys 20:362201Google Scholar
- 17.Jeon IY, Choi HJ, Choi M, Seo JM, Jung SM, Kim MJ, Zhang S, Zhang L, Xia Z, Dai L, Park N, Baek JB (2013) Facile, scalable synthesis of edge-halogenated graphene nanoplatelets as efficient metal-free eletrocatalysts for oxygen reduction reaction. Sci Rep 3:1810Google Scholar
- 24.Tan YZ, Yang B, Parvez K, Narita A, Osella S, Beljonne D, Feng X, Müllen K (2013) Atomically precise edge chlorination of nanographenes and its application in graphene nanoribbons. Nat Commun 4:2646Google Scholar
- 25.Zheng J, Liu HT, Wu B, Di CA, Guo YL, Wu T, Yu G, Liu YQ, Zhu DB (2012) Production of graphite chloride and bromide using microwave sparks. Sci Rep 2:662Google Scholar
- 30.Frisch MJ, Trucks GW, Schlegel HB et al (2009) Gaussian 09, Revision D.01. Wallingford, Gaussian Inc.Google Scholar
- 31.Kim K, Coh S, Kisielowski C, Crommie MF, Louie SG, Cohen ML, Zettl A (2013) Atomically perfect torn graphene edges and their reversible reconstruction. Nat Commun 4:2723Google Scholar