Preparation, structure, and properties of tris(trimethylsilyl)silyl- substituted anthracenes: Realization of ideal conformation for σ-π conjugation involving eclipse of Si-Si σ-bond with p-orbital of aromatic ring

Chemistry Letters

Volumn 35, Issue 9, 2006, Pages 1022-1023

  Shimizu, Masaki ^a   Oda, Katsunari ^a   Bando, Tomoaki ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845260108     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2006.1022     Document Type: Article

References (16)

1. H. Sakurai, J. Organomet. Chem. 1980, 200, 261.
2. H. Sakurai, S. Tasaka, M. Kira, J. Am. Chem. Soc. 1972, 94, 9285.
3. Examples of TTMSS-substituted aromatics: a) M. J. Sanganee, P. G. Steel, D. K. Whelligan, J. Org. Chem. 2003, 68, 3337.
4. b) L. F. Brough, R. West, J. Organomet. Chem. 1982, 229, 113.
5. c) H. J. Sipe, Jr., R. West, J. Organomet. Chem. 1974, 70, 353.
6. d) M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 23, 85.
7. Preparation and such properties as photoelectron spectra, first ionization energy, and ESR/ENDOR spectra of 1,4-bis(TTMSS)benzene were reported without any crystal structures: a) H. Bock, J. Meuret, K. Ruppert, Angew. Chem., Int. Ed. Engl. 1993, 32, 414.
8. b) H. Bock, J. Meuret, R. Baur, K. Ruppert, J. Organomet. Chem. 1993, 446, 113;
9. See also, H. Bock, B. Solouki, Chem. Rev. 1995, 95, 1161.
10. In Refs. 4a and 4b, a single crystal structure of 1,4- bis[(trimethylsilyl)methyl]benzene is reported. One benzylic carbonsilicon bond is shown to be aligned with the plane of the benzene ring.
11. Examples of 9- and 9,10-silylated anthracenes: a) S. Kyushin, M. Ikarugi, M. Goto, H. Hiratsuka, H. Matsumoto, Organometallics 1996, 15, 1067.
12. b) T. Karatsu, T. Shibata, A. Nishigaki, K. Fukui, A. Kitamura, Chem. Lett. 2001, 994, and references cited therein.
13. See Supporting Information.
14. 2 = 0.143 (all data). CCDC-613895.
15. 2 = 0.137 (all data). CCDC-613896.
16. For fluorescence of aryldisilanes, see: H. Sakurai, H. Sugiyama, M. Kira, J. Phys. Chem. 1990, 94, 1837, and references cited therein.