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Issue 16, 2019
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Site-selective functionalization of Si6R6 siliconoids

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Abstract

The recent progress in the synthesis of partially substituted neutral silicon clusters (siliconoids) revealed unique structures and electronic anisotropies that are reminiscent of bulk and nano surfaces of silicon. Here, we report the selective 2-lithiation of the global minimum Si6R6 siliconoid at a different vertex than in the previously reported isomeric 4-lithiated derivative (R = 2,4,6-iPr3C6H2). In order to enable an intuitive distinction of the vertices of the global minimum Si6R6 scaffold (which can be considered the silicon analogue of benzene in terms of thermodynamic stability), we introduce a novel nomenclature in analogy to the orthometapara nomenclature of disubstituted benzenes. By treatment of the 2-lithiated Si6 cluster with Me3SiCl, SiCl4 H3B·SMe2, (Me2N)2PCl as well as with carboxylic acid chlorides RCOCl (R = tBu, Ph) various 2-functionalized Si6 clusters were obtained and characterized in solution and – in most cases – the solid state. The structural and spectroscopic effect of the position of the newly introduced functional group is discussed by comparison to the corresponding 4-functionalized derivatives.

Graphical abstract: Site-selective functionalization of Si6R6 siliconoids

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Publication details

The article was received on 14 Dec 2018, accepted on 07 Mar 2019 and first published on 14 Mar 2019


Article type: Edge Article
DOI: 10.1039/C8SC05591B
Citation: Chem. Sci., 2019,10, 4523-4530
  • Open access: Creative Commons BY-NC license
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    Site-selective functionalization of Si6R6 siliconoids

    Y. Heider, N. E. Poitiers, P. Willmes, K. I. Leszczyńska, V. Huch and D. Scheschkewitz, Chem. Sci., 2019, 10, 4523
    DOI: 10.1039/C8SC05591B

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