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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Application of the sila-Friedel-Crafts reaction to the synthesis of π-extended silole derivatives and their properties
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Application of the sila-Friedel-Crafts reaction to the synthesis of π-extended silole derivatives and their properties

机译：sila-Friedel-Crafts反应在π-扩展的silole衍生物的合成及其性质中的应用

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摘要

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.
机译：分子内硅烷-Friedel-Crafts反应被开发为构建二苯并甲硅烷基骨架的新方法。该反应在温和条件下进行，以相对较高的收率得到目标，表明其可作为通用合成方法使用。该反应可用于合成π-扩展的硅油石衍生物，例如梯型硅芴8和螺环型硅二芴9。此外，利用sila-Friedel-Crafts反应作为多个倍数来合成二维延伸的硅油石衍生物。分子内环化得以实现，包括首次合成三硅富马来烯18。X硅碳富马来烯18的X射线晶体学分析表明，主要的π构架具有平面性，而与Sumanene及其硫类似物三硫富马来烯具有碗形结构。在紫外可见吸收光谱中，与六丁氧基三亚苯基22相比，三苯基烯基硅酮18和19的吸收带略有红移。在18和19的较长波长区域也观察到了弱吸收带，这是由于Silole骨架的σ*-π*共轭。另外，18和19在二氯甲烷和固态下显示蓝色荧光。

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