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Substituted tetra-2,3-pyrazinoporphyrazines. Part II. Bis(tri-n-hexylsiloxy)silicon derivatives

 

作者: Svetlana V. Kudrevich,   Johan E. Van Lier,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1996)
卷期: Volume 74, issue 9  

页码: 1718-1723

 

ISSN:0008-4042

 

年代: 1996

 

DOI:10.1139/v96-189

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

Dichlorosilicon complexes of substituted tetra-2,3-pyrazinoporphyrazines were obtained via condensation of 2,3-dicyanopyrazine, 2,3-dicyano-5,6-diphenylpyrazine, 2,3-dicyanoquinoxaline, 2,3-dicyano-benzo[f]quinoxaline, and 2,3-dicyano-dibenzo[f,h]quinoxaline with silicon tetrachloride in the presence of urea, quinoline, and tri-n-butylamine. Hydrolysis of the Si-Cl bond in concentrated H2SO4, followed by treatment with 0.01 N NaOH and aqueous NH3, afforded the corresponding dihydroxides, which were converted to the bis(tri-n-hexylsiloxy)silicon derivatives via reaction with tri(n-hexyl)silane in 3-picoline (2,4,6-collidine) in the presence of tri-n-butylamine. The axial tri-n-hexylsiloxy substituents at the central silicon atom prevent aggregation in organic solvents, permitting detailed studies on the effects of structural modifications on the electronic spectra of tetraazaphthalocyanines. Our data show that each benzo ring addition, angularly condensed to the tetra-2,3-quinoxalinoporphyrazine, induces a hypsochromic shift (~ 10–15 nm) of the main absorption maximum.Keywords: phthalocyanine, aza analog, bis(tri-n-hexylsiloxy)silicon complex.

 

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