1-Silacyclopenta-2,4-dienes (siloles) have unique photophysical and electronic properties that give them potential application in electroluminescent devices. Conjugation between exocyclic Si-C and endocyclic  diene bonds (s*-p*) within the silole allows for a low LUMO energy level relative to its carbon-only analog, cyclopentadiene. This energy gap can be �tuned� by altering the substituents on the silole ring. In 1972,  Kumada et al (JACS, 1972, 94, 9263) discovered a synthetic method to alter groups in the 2,3,4, and 5 positions of the silole in a one-pot reaction. Reactions attempting to attach 1-naphthyl, 3-quinolinyl,  4-isoquinolinyl, and 4-benzonirilyl groups to the silole and the resulting products will be described. The appropriate diarylacetylenes (i.e. bis(1-naphthyl)acetylene) were reacted with 1,1,2,2-tetramethyldisilane using NiCl2(PEt3)2 as a catalyst. Products were purified by flash column chromatography. The resulting compounds were investigated using mass spectrometry, nuclear magnetic resonance, and x-ray crystallography.

Synthesis of 1-silacyclopenta-2,4-dienes

239th National Meeting (2010)

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