Issue 39, 2006

Comparative studies of the geometric and electronic properties of 1,1-disubstituted-2,3,4,5-tetraphenylsiloles and 1,1,2,2-tetramethyl-3,4,5,6-tetraphenyl-1,2-disila-3,5-cyclohexadiene

Abstract

We present an experimental and density functional theory comparison of the geometric structure, electronic characteristics and optical properties of 1,1-dimethyl-2,3,4,5-tetraphenylsilole (I), 1,1-(propane-1,3-diyl)-2,3,4,5-tetraphenylsilole (II), 1,1-dimethoxy-2,3,4,5-tetraphenylsilole (III) and 1,1,2,2-tetramethyl-3,4,5,6-tetraphenyl-1,2-disila-3,5-cyclohexadiene (IV). The molecular structures of IIIV have been determined using X-ray crystallography and are compared to the previously reported structure of I. Many characteristics of IV are significantly different from those of IIII, due to the presence of the additional silicon atom. In contrast to IIII, which have planar central rings, IV has a non-planar ring conformation due to the presence of two approximately tetrahedrally coordinated silicon atoms. Cyclic voltammetry suggests that IIII are reduced at similar potentials to that for tris(8-hydroquinolinato)aluminium and that IV is more readily oxidizable than IIII. Additionally, while IV is non-emissive in both solution and the solid state, the three siloles are fluorescent in the solid state. For the four compounds, we have calculated the intramolecular reorganization energies for electron- and hole-transfer reactions, ionization potentials and electron affinities.

Graphical abstract: Comparative studies of the geometric and electronic properties of 1,1-disubstituted-2,3,4,5-tetraphenylsiloles and 1,1,2,2-tetramethyl-3,4,5,6-tetraphenyl-1,2-disila-3,5-cyclohexadiene

Supplementary files

Article information

Article type
Paper
Submitted
13 Apr 2006
Accepted
21 Jul 2006
First published
14 Aug 2006

J. Mater. Chem., 2006,16, 3814-3822

Comparative studies of the geometric and electronic properties of 1,1-disubstituted-2,3,4,5-tetraphenylsiloles and 1,1,2,2-tetramethyl-3,4,5,6-tetraphenyl-1,2-disila-3,5-cyclohexadiene

X. Zhan, C. Risko, A. Korlyukov, F. Sena, T. V. Timofeeva, M. Yu. Antipin, S. Barlow, J. Brédas and S. R. Marder, J. Mater. Chem., 2006, 16, 3814 DOI: 10.1039/B605343B

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