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

doi:10.6023/cjoc201306034

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

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硅硅键与苯环之间的相互作用：不对称取代1,2-二苯基二硅烷的紫外吸收性质

谷广娜, 孙怀林, 周秀中

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 E-mail:sunhl@nankai.edu.cn
基金资助:
国家自然科学基金（No.20834002）、天津市自然科学基金（No.08JCZDJC21600）和高等学校博士学科点专项科研基金（No.20090031110012）资助项目.

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

Gu Guangna, Sun Huailin, Zhou Xiuzhong

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).

1. Interaction of Silicon-Silicon Bonds and Phenyl Rings: UV Absorption Properties of Unsymmetrically Substituted 1,2 Diphenyltetramethyldisilanes.PDF(289KB)

Abstract

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

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Gu Guangna, Sun Huailin, Zhou Xiuzhong. Interaction of Silicon-Silicon Bonds and Phenyl Rings: UV Absorption Properties of Unsymmetrically Substituted 1,2 Diphenyltetramethyldisilanes[J]. Chin. J. Org. Chem., 2014, 34(2): 349-354.

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硅硅键与苯环之间的相互作用：不对称取代1,2-二苯基二硅烷的紫外吸收性质

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

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