Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (2): 349-354.DOI: 10.6023/cjoc201306034 Previous Articles     Next Articles



谷广娜, 孙怀林, 周秀中   

  1. 南开大学化学系 天津 300071
  • 收稿日期:2013-06-21 修回日期:2013-10-09 发布日期:2013-10-28
  • 通讯作者: 孙怀林
  • 基金资助:


Interaction of Silicon-Silicon Bonds and Phenyl Rings: UV Absorption Properties of Unsymmetrically Substituted 1,2 Diphenyltetramethyldisilanes

Gu Guangna, Sun Huailin, Zhou Xiuzhong   

  1. Department of Chemistry, Nankai University, Tianjin 300071
  • Received:2013-06-21 Revised:2013-10-09 Published:2013-10-28
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 20834002), the Natural Science Foundation of Tianjin City, and the Research Found for the Doctoral Program of High Education (No. 20090031110012).

The interaction of silicon-silicon-bonds and phenyl-systems in phenyldisilanes and the resulted characteristic UV absorptions have been one of the fundamental issues of organosilicon chemistry. However, the interaction between two phenyl groups and the central silicon-silicon bond in 1,2-diphenyltetramethyldisilanes and its correlation with the characteristic UV absorptions remain uncompletely solved. In this paper, a series of unsymmetric substituted 1,2-diphenyltetramethyldisilanes, namely C6H5SiMe2SiMe2C6H4-p-COMe (3), p-MeOC6H4SiMe2SiMe2C6H4-p-COMe (4), C6H5SiMe2SiMe2C6H4-p-NMe2 (5) and p-MeOC6H4SiMe2SiMe2C6H4-p-NMe2 (6), have been synthesized and characterized by 1H NMR, 13C NMR, IR and elemental analyses, and their UV absorption properties were studied. It is found that each of the compounds exhibits two characteristic absorption bands at the long wavelength region of the UV spectra, which corresponds to the absorptions produced when individual substituted phenyl groups are linked to silicon-silicon bonds. No obvious bathochromic shifts due to interaction between two substituted phenyl groups through the silicon-silicon bond have been observed. This indicates that the traditional explanation of characteristic UV absorptions of phenyldisilanes in terms of conjugation between silicon-silicon bonds and phenyl groups should be re-examined.

Key words: phenyldisilanes, silicon-silicon bonds, UV absorption, σ-&pi, conjugation, charge transfer