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Issue 39, 2010
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Application of the sila-Friedel–Crafts reaction to the synthesis of π-extended silole derivatives and their properties

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Abstract

The intramolecular sila-Friedel–Crafts reaction was developed as a new method for the construction of a dibenzosilole skeleton. This reaction proceeds under mild conditions to afford the target in relatively good yield, indicating its availability as a versatile synthetic method. This reaction can be applied to the synthesis of π-extended silole derivatives such as ladder-type silafluorene 8 and spiro-type silabifluorene 9. Furthermore, the synthesis of two-dimensionally extended silole derivatives utilizing the sila-Friedel–Crafts reaction as the multiple intramolecular cyclization was achieved, including the first synthesis of trisilasumanene 18. The X-ray crystallographic analysis of trisilasumanene 18 demonstrated the planarity in the main π-framework, in contrast to sumanene and its sulfur analogue, trithiasumanene, bearing the bowl-shaped structures. In the UV-vis absorption spectra, the absorption bands of triphenylenosiloles 18 and 19 were slightly red-shifted compared to that of hexabutoxytriphenylene 22. The weak absorption bands were also observed in the longer-wavelength region in 18 and 19, which is derived from σ*–π* conjugation of the silole skeletons. In addition, 18 and 19 showed the blue fluorescence in dichloromethane and in the solid state.

Graphical abstract: Application of the sila-Friedel–Crafts reaction to the synthesis of π-extended silole derivatives and their properties

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Publication details

The article was received on 15 Mar 2010, accepted on 22 Jul 2010 and first published on 07 Sep 2010


Article type: Paper
DOI: 10.1039/C0DT00136H
Citation: Dalton Trans., 2010,39, 9329-9336
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    Application of the sila-Friedel–Crafts reaction to the synthesis of π-extended silole derivatives and their properties

    S. Furukawa, J. Kobayashi and T. Kawashima, Dalton Trans., 2010, 39, 9329
    DOI: 10.1039/C0DT00136H

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