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Science and Technology of Advanced Materials Volume 19, 2018 - Issue 1
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Focus on New Materials Science and Element Strategy

π-Electron systems containing Si=Si double bonds

Tsukasa MatsuoDepartment of Applied Chemistry, Faculty of Science and Engineering, Kindai University, Osaka, JapanCorrespondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-5538-8044
ORCID Icon &
Naoki HayakawaDepartment of Applied Chemistry, Faculty of Science and Engineering, Kindai University, Osaka, Japan
Pages 108-129 | Received 15 Sep 2017, Accepted 05 Dec 2017, Published online: 07 Feb 2018

Figures & data

Figure 1. Examples of stable unsaturated silicon compounds.

Figure 1. Examples of stable unsaturated silicon compounds.

Figure 2. Rind groups.

Figure 2. Rind groups.

Figure 3. Disilenes 8 and 15.

Figure 3. Disilenes 8 and 15.

Figure 4. Molecular structures of 16 (a) and 17 (b) determined by X-ray crystallography.

Figure 4. Molecular structures of 16 (a) and 17 (b) determined by X-ray crystallography.

Figure 5. Photographs of the THF solutions of 16–19 at room temperature: (a) under room light; (b) under 360 nm UV light.

Figure 5. Photographs of the THF solutions of 16–19 at room temperature: (a) under room light; (b) under 360 nm UV light.

Figure 6. Disilenes 22 and 23.

Figure 6. Disilenes 22 and 23.

Figure 7. Molecular structures of 24 (a), 25a (b), and 25b (c) determined by X-ray crystallography.

Figure 7. Molecular structures of 24 (a), 25a (b), and 25b (c) determined by X-ray crystallography.

Figure 8. Photographs of the THF solutions (left) and solid in the air (right) of 24 and 25: (a) under room light; (b) under 365 nm UV light.

Figure 8. Photographs of the THF solutions (left) and solid in the air (right) of 24 and 25: (a) under room light; (b) under 365 nm UV light.

Figure 9. Frontier molecular orbitals of 24, 25a, and 25b together with the energy levels.

Figure 9. Frontier molecular orbitals of 24, 25a, and 25b together with the energy levels.

Figure 10. (a) The configuration of the EL device; (b) EL from the device at a 5 V applied voltage.

Figure 10. (a) The configuration of the EL device; (b) EL from the device at a 5 V applied voltage.

Figure 11. Molecular structure of 29 determined by X-ray crystallography.

Figure 11. Molecular structure of 29 determined by X-ray crystallography.

Figure 12. Photographs of the solutions of 29 under 365 nm UV light: (a) hexane; (b) THF; (c) acetone.

Figure 12. Photographs of the solutions of 29 under 365 nm UV light: (a) hexane; (b) THF; (c) acetone.

Figure 13. Selected molecular orbitals of 29 together with the energy levels.

Figure 13. Selected molecular orbitals of 29 together with the energy levels.

Figure 14. Disilenes 31–33.

Figure 14. Disilenes 31–33.

Figure 15. Disilenes 34 and 35.

Figure 15. Disilenes 34 and 35.

Figure 16. Photographs of the THF solutions of 29: (a) before irradiation; (b) after irradiation at 530 nm.

Figure 16. Photographs of the THF solutions of 29: (a) before irradiation; (b) after irradiation at 530 nm.

Figure 17. Oligothiophenes 36.

Figure 17. Oligothiophenes 36.

Figure 18. Molecular structures of (a) 37a and (b) 38a determined by X-ray crystallography.

Figure 18. Molecular structures of (a) 37a and (b) 38a determined by X-ray crystallography.

Figure 19. Rotational isomers of 37 and 38.

Figure 19. Rotational isomers of 37 and 38.

Figure 20. Photographs of the THF solutions: (a) 37 under room light; (b) 38 under room light; (c) 38 under 365 nm UV light.

Figure 20. Photographs of the THF solutions: (a) 37 under room light; (b) 38 under room light; (c) 38 under 365 nm UV light.

Figure 21. Frontier molecular orbitals of 37a and 38a together with the energy levels.

Figure 21. Frontier molecular orbitals of 37a and 38a together with the energy levels.

Figure 22. Compounds 5, 7, and 41–43.

Figure 22. Compounds 5, 7, and 41–43.

Figure 23. Compounds 44–47.

Figure 23. Compounds 44–47.

Scheme 1. Synthesis of compounds 8a and 9.

Scheme 1. Synthesis of compounds 8a and 9.

Scheme 2. Synthesis of compounds 10 and 11.

Scheme 2. Synthesis of compounds 10 and 11.

Scheme 3. Synthesis of compounds 16–19.

Scheme 3. Synthesis of compounds 16–19.

Table 1. X-ray structural parameters of disilenes.

Table 2. Photophysical data for disilenes.

Scheme 4. Synthesis of compound 24.

Scheme 4. Synthesis of compound 24.

Scheme 5. Synthesis of compound 25.

Scheme 5. Synthesis of compound 25.

Scheme 6. Synthesis of compound 29.

Scheme 6. Synthesis of compound 29.

Scheme 7. Synthesis of compound 37.

Scheme 7. Synthesis of compound 37.

Scheme 8. Synthesis of compound 38.

Scheme 8. Synthesis of compound 38.

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