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Volumn 26, Issue 16, 2007, Pages 4048-4053

Synthesis and properties of a kinetically stabilized 9-silaphenanthrene

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; MOLECULAR STRUCTURE; REACTION KINETICS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; X RAY CRYSTALLOGRAPHY;

EID: 34547818091     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700347z     Document Type: Article
Times cited : (38)

References (50)
  • 19
    • 1242271354 scopus 로고    scopus 로고
    • For recent reviews on sila- and germaaromatic compounds kinetically stabilized with a Tbt group, see: a
    • For recent reviews on sila- and germaaromatic compounds kinetically stabilized with a Tbt group, see: (a)Tokitoh, N. Acc. Chem. Res. 2004, 37,86.
    • (2004) Acc. Chem. Res , vol.37 , Issue.8 , pp. 6
    • Tokitoh, N.1
  • 28
    • 34547730599 scopus 로고    scopus 로고
    • When a 2.2 equiv molar amount of lithium naphthalenide was added to a THF solution of 4 at -78 °C, the mixture of 4 and bromosilane 6 was obtained. The use of a 4.2 equiv molar amount of lithium naphthalenide resulted in the formation of compounds 5 and 6 We postulated the mechanism where the silylene was generated by the reduction of the dibromosilane moiety inserted intramolecularly into the C-Br bond, and then hydrosilane 5 was formed by the further reduction of the Si-Br bond of 6 by lithium naphthalenide.
    • When a 2.2 equiv molar amount of lithium naphthalenide was added to a THF solution of 4 at -78 °C, the mixture of 4 and bromosilane 6 was obtained. The use of a 4.2 equiv molar amount of lithium naphthalenide resulted in the formation of compounds 5 and 6 We postulated the mechanism where the silylene was generated by the reduction of the dibromosilane moiety inserted intramolecularly into the C-Br bond, and then hydrosilane 5 was formed by the further reduction of the Si-Br bond of 6 by lithium naphthalenide.
  • 29
    • 33645680741 scopus 로고    scopus 로고
    • The photophysical and photochemical processes of 9-silaphenanthrene derivatives at 77 K have been reported, and the fluorescence spectrum of 9-Tbt-9-silaphenanthrene is shown there. The lifetimes of the fluorescence of Tbt-9-silaphenanthrene were 6.9 ns (94%) and 2.4 ns (6%). Hiratsuka, H.; Horiuchi, H.; Furukawa, Y.; Watanabe, H.; Ishihara, A.; Okutsu, T.; Tobita, S.; Yoshinaga, T.; Shinohara, A.; Tokitoh, N.; Oba, M.; Nishiyama K. J. Phys. Chem. A 2006, 110, 3868.
    • The photophysical and photochemical processes of 9-silaphenanthrene derivatives at 77 K have been reported, and the fluorescence spectrum of 9-Tbt-9-silaphenanthrene is shown there. The lifetimes of the fluorescence of Tbt-9-silaphenanthrene were 6.9 ns (94%) and 2.4 ns (6%). Hiratsuka, H.; Horiuchi, H.; Furukawa, Y.; Watanabe, H.; Ishihara, A.; Okutsu, T.; Tobita, S.; Yoshinaga, T.; Shinohara, A.; Tokitoh, N.; Oba, M.; Nishiyama K. J. Phys. Chem. A 2006, 110, 3868.
  • 30
    • 34547819619 scopus 로고    scopus 로고
    • Calculated at the B3LYP/6-31G(d) level. Results of the theoretical calculations for lb are shown in the Supporting Information.
    • Calculated at the B3LYP/6-31G(d) level. Results of the theoretical calculations for lb are shown in the Supporting Information.
  • 31
    • 1842555193 scopus 로고    scopus 로고
    • -1; see: Leites, L. A.; Bukalov, S. S.; Zabula, A. V.; Garbuzova, I. A.; Moser, D. F.; West, R. J. Am. Chem. Soc. 2004, 126, 4114.
    • -1; see: Leites, L. A.; Bukalov, S. S.; Zabula, A. V.; Garbuzova, I. A.; Moser, D. F.; West, R. J. Am. Chem. Soc. 2004, 126, 4114.
  • 35
    • 34547766372 scopus 로고    scopus 로고
    • The C-C bond lengths of phenanthrene are 1.372-1.457 Å. See: Trotter, J. Acta Crystallogr.,1963, 76, 605.
    • The C-C bond lengths of phenanthrene are 1.372-1.457 Å. See: Trotter, J. Acta Crystallogr.,1963, 76, 605.
  • 36
    • 0006875989 scopus 로고    scopus 로고
    • Although the degree of T-shaped CH-π interaction should be discussed on the basis of the distance between the center of the aromatic ring and the aromatic plane, it is somewhat difficult to define the center of the 9-silaphenanthrene ring due to the slight deformation of the skeleton. It was reported that the T-shaped CH-π interaction in a benzene dimer should be highly effective when the distance between the center of the aromatic ring and the aromatic plane is ca. 5.0 Å; that is, that between the C atom at the edge and the aromatic plane is ca. 3.6 Å;. The C-C distance (ca 3.7 Å) due to the CH-π interaction observed for la should be similar to those observed for phenanthrene. See: (a) Mason, R. Mol. Phys. 1961, 4, 413
    • Although the degree of T-shaped CH-π interaction should be discussed on the basis of the distance between the center of the aromatic ring and the aromatic plane, it is somewhat difficult to define the center of the 9-silaphenanthrene ring due to the slight deformation of the skeleton. It was reported that the T-shaped CH-π interaction in a benzene dimer should be highly effective when the distance between the center of the aromatic ring and the aromatic plane is ca. 5.0 Å; that is, that between the C atom at the edge and the aromatic plane is ca. 3.6 Å;. The C-C distance (ca 3.7 Å) due to the CH-π interaction observed for la should be similar to those observed for phenanthrene. See: (a) Mason, R. Mol. Phys. 1961, 4, 413.
  • 50
    • 0004150157 scopus 로고    scopus 로고
    • Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany
    • Sheldrick, G. M. SHELX-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
    • (1997) SHELX-97
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.