Issue 39, 2010

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

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

Supplementary files

Article information

Article type
Paper
Submitted
15 Mar 2010
Accepted
22 Jul 2010
First published
07 Sep 2010

Dalton Trans., 2010,39, 9329-9336

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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