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Progress in Chemistry 2012, Vol. 24 Issue (04): 556-567 Previous Articles   Next Articles

• Review •

Chemistry and Application of Dicarbadodecaborane and Its Derivatives

Zhao Juan, Huang Pengcheng, Chen Gong, Zhan Maosheng   

  1. Materials Science and Engineering School, Beihang University, Beijing 100191, China
  • Received: Revised: Online: Published:
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Dicarba-closo-dodecaborane (carborane, C2B10H12) containing two carbon atoms and ten boron atoms adopts nearly icosahedral geometry in which the carbon and boron atoms are hexacoordinate. The compound exists as ortho-, meta-and para-isomers. Due to the strong electron-acceptor properties of the cluster, massive bulk and three-dimensional rigidity, carborane and its derivatives possess remarkable thermal and chemical stability. Besides, the ready solubility makes the compound and its derivatives widely applied. There are two common methods for synthesis of carborane and carborane derivatives, including the “alkyne insertion” methodology and the method based on the substitution reaction with carboranyl lithium. In this paper, the chemical reactions and functionalization of carborane and its derivatives are summarized, especially the substitution reactions on carbon atoms and boron atoms, the cycloaddition reaction and metal-carborane complexation. Futhermore, due to the excellent heat stability and high electronic delocalization, the carborane derivatives can be utilized as functional materials. Also, carborane derivatives can be applied in boron neutron capture therapy (BNCT) for the high boron content of carborane. Meanwhile, the metal-carborane complexes containing bulky carborane as ligands are reported to be available as the efficient catalysts. Herein, the advances in the application of the carborane derivatives in recent years are reviewed.
Contents
1 Introduction
2 Preparation, structure and properties of carborane
3 Chemical reaction of carborane
3.1 C-H functionalization
3.2 B-H functionalization
3.3 Cycloaddition reaction
3.4 Metal-carborane complexes
4 Application of carborane and its derivatives
4.1 Functional materials
4.2 Biological medicine
4.3 Catalysts
4.4 Others
5 Conclusion and outlook
Key words: dicarba-closo-dodecaborane, functionalization, heat stability, high boron content

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