Nouveaux dérivés du silacyclopentadiène

Brunet, J. C.; Lemahieu, C.

doi:10.1016/s0022-328x(00)84228-x

Cited by 10 publications

(1 citation statement)

References 7 publications

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“…In addition, they are capable of binding to metal ions to form extended coordination polymers . Although 1,1-difunctionalizd or 2,5-difunctionalized siloles have been well documented, examples of siloles functionalized at the 2,3,4,5-positions such as D are still rare because the synthetic methods available for 2,3,4,5-functionalized siloles are quite limited. In this work, we report the synthesis, structures, and fluorescent and electroluminescent properties of new 2,3,4,5-functionalized silole compounds based on indolyl, 7-azaindolyl, 2,2‘-dipyridylamino, and (1-naphthyl)phenylamino groups.…”

Section: Introductionmentioning

confidence: 99%

2,3,4,5-Tetrafunctionalized Siloles: Syntheses, Structures, Luminescence, and Electroluminescence

et al. 2004

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Six new diethynylsilane compounds with the general formula Si(C⋮C−R)2R‘2 (R = p - N-indolylphenyl, R‘ = Me, 1; R‘ = Ph, 2; R = p - N-7-azaindolylphenyl, R‘ = Me, 3; R‘ = Ph, 4; R = p-2,2‘-dipyridylaminophenyl, R‘ = Me, 5; R‘ = Ph, 6) have been synthesized and fully characterized. Compounds 1, 2, and 4 have been found to undergo intramolecular cyclization in the presence of Li-naphthyl to form the corresponding 2,5-dilithiosiloles, which after methylation by CH3I or undergoing Pd-catalyzed cross-coupling reactions with the appropriate arylbromide produced six new silole compounds: 1,1-diphenyl-2,5-dimethyl-3,4-bis(4-N-7-azaindoylphenyl)silole (7), 1,1-diphenyl-2,3,4,5-tetrakis(4-N-indoylphenyl)silole (8), 1,1-dimethyl-2,5-bis(4-N-7-azaindoylphenyl)-3,4-bis(4-N-indoylphenyl)silole (9), 1,1-dimethyl-2,5-bis(p-2,2‘-dipyridylaminophenyl)-3,4-(4-N-indoylphenyl)silole (10), 1,1-dimethyl-2,5-bis(4-(N-1-naphthylphenylamino)phenyl)-3,4-bis(4-N-indoylphenyl)silole (11), and 1,1-dimethyl-2,5-bis(4‘-(N-1-naphthylphenylamino)biphenyl)-3,4-bis(4-N-indoylphenyl)silole (12). Compounds 8−12 are a new class of silole molecules that are functionalized at the 2-, 3-, 4-, and 5-positions by indolylphenyl, 7-azaindolylphenyl, 2,2‘-dipyridylaminophenyl, (N-1-naphthyl)(N-phenyl)aminophenyl, or (N-1-naphthyl)(N-phenyl)aminobiphenyl. The structures of compounds 3, 5, and 8 were determined by single-crystal X-ray diffraction analysis. Siloles 8−12 emit a green color in solution and the solid state, while in contrast silole 7 emits a blue color with the emission maximum at 445 nm. The effects of substituent groups at different positions of the silole ring on structures and luminescent properties have been examined. A single-layer EL device with compound 11 being sandwiched between the ITO anode and the LiF/Al cathode layers has been fabricated successfully.

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Section: Introductionmentioning

confidence: 99%