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Issue 3, 2002

Synthesis and characterisation of new oligoacetylenic silanes

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Abstract

Synthetic routes to a series of novel oligoacetylenic silanes with or without (hetero)aromatic bridges have been developed. The compound Me3SiC[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]CSiMe3 was first prepared, which was selectively desilylated with CaCO3 in methanol at room temperature to afford the mono-protected bis(alkynyl) silane Me3SiC[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]CH in moderate yield. Treatment of this mono-protected species with nBuLi, followed by silylation with Ph2SiCl2, gives a good yield of Me3SiC[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]CSiMe3, with alternating silicon and acetylene units. A range of linear silicon-linked oligoalkynes containing phenylene, bithienylene and anthrylene rings, HC[triple bond, length half m-dash]CRC[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]CRC[triple bond, length half m-dash]CH and HC[triple bond, length half m-dash]CRC[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]CRC[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]CRC[triple bond, length half m-dash]CH (R = 1,4-phenylene, 5,5′-bithienylene or 9,10-anthrylene), were synthesised by condensation reactions of Ph2SiCl2 with the components obtained in situ from a HC[triple bond, length half m-dash]CRC[triple bond, length half m-dash]CH–nBuLi mixture in THF and the products were isolated by chromatography on silica. All these new compounds have been characterised by IR, 1H and 13C NMR and UV/VIS spectroscopies and mass spectrometry. The single-crystal X-ray structure of HC[triple bond, length half m-dash]C(p-C6H4)C[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]C(p-C6H4)C[triple bond, length half m-dash]CSi(Ph)2C[triple bond, length half m-dash]C(p-C6H4)C[triple bond, length half m-dash]CH has been determined, showing that two silicon atoms and six acetylene units constitute the backbone of the molecule.

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Article information


Submitted
21 Aug 2001
Accepted
20 Nov 2001
First published
19 Feb 2002

New J. Chem., 2002,26, 354-360
Article type
Paper

Synthesis and characterisation of new oligoacetylenic silanes

W. Wong, A. W.-M Lee, C. Wong, G. Lu, H. Zhang, T. Mo and K. Lam, New J. Chem., 2002, 26, 354 DOI: 10.1039/B108510G

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