Journal of Materials Science

, Volume 50, Issue 15, pp 5183–5190 | Cite as

Bromination of graphene with pentagonal, hexagonal zigzag and armchair, and heptagonal edges

  • Jungpil Kim
  • Yasuhiro YamadaEmail author
  • Ryo Fujita
  • Satoshi Sato
Original Paper


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.


Naphthalene Density Functional Theory Calculation Azulene Graphene Edge Zigzag Edge 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



This work was supported by Japan Interaction in Science and Technology Forum.

Supplementary material

10853_2015_9066_MOESM1_ESM.docx (286 kb)
Supplementary material 1 (docx 285 kb)


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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Jungpil Kim
    • 1
  • Yasuhiro Yamada
    • 1
    Email author
  • Ryo Fujita
    • 1
  • Satoshi Sato
    • 1
  1. 1.Graduate School of EngineeringChiba UniversityChibaJapan

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