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Synthesis and spectroscopic studies of Arylethynylsilanes

A variety of arylethynylsilanes (Ar-CCC6H4CC)nSiMe4−n were prepared successfully by reaction of the corresponding chlorosilanes Me4−nSiCln with ArCCC6H4CCM (M=Li, MgBr), which was prepared by treatment of ethynyl(diarylethyne)s ArCCC6H4CCH with BuLi or MeMgBr. The ethynyl(diarylethyne)s...

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Bibliographic Details
Main Authors: Shao, Guang (Author) , Gleiter, Rolf (Author)
Format: Article (Journal)
Language:English
Published: 12 March 2007
In: Chemistry
Year: 2007, Volume: 2, Issue: 4, Pages: 489-498
ISSN:1861-471X
DOI:10.1002/asia.200700007
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/asia.200700007
Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/asia.200700007/abstract
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Author Notes:Guang Shao, Akihiro Orita, Koji Nishijima, Kanako Ishimaru, Makoto Takezaki, Kan Wakamatsu, Rolf Gleiter, and Junzo Otera
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Summary:A variety of arylethynylsilanes (Ar-CCC6H4CC)nSiMe4−n were prepared successfully by reaction of the corresponding chlorosilanes Me4−nSiCln with ArCCC6H4CCM (M=Li, MgBr), which was prepared by treatment of ethynyl(diarylethyne)s ArCCC6H4CCH with BuLi or MeMgBr. The ethynyl(diarylethyne)s were readily prepared in good yields by the double-elimination method: addition of lithium hexamethyldisilazide to a mixture of ArCH2SO2Ph, TMSCCC6H4CHO, and ClP(O)(OEt)2, followed by desilylation. In the tetrakis(arylethynyl)silanes (ArCCC6H4CC)4Si thus prepared, through-space conjugation of four triple bonds on the silicon atom emerges as a result of participation of the silicon orbitals in the acetylenic π orbitals. This participation enhances the emissive quantum yields of arylethynylsilanes with an increase in the number of arylethynyl moieties on silicon: quantum yields of emission (ΦF) of 0.72 for (MeOC6H4CCC6H4CC)4Si, 0.53 for (MeOC6H4CCC6H4CC)2SiMe2, and 0.47 for MeO-C6H4CCC6H4CCSiMe3 were obtained. Although this enhancement effect was also observed in the phenylethynylarylsilane (MeOC6H4CCC6H4)2SiMe2, the bis(arylethynyl)disilane (MeOC6H4CCC6H4CC-SiMe2)2 exhibited non-enhanced emission.
Item Description:Gesehen am 28.09.2017
Physical Description:Online Resource
ISSN:1861-471X
DOI:10.1002/asia.200700007

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