Phthalocyanines and related compounds: XLIII. Synthesis of poly[phenyl(alkyl)sulfanyl]-substituted phthalonitriles and some phthalocyanines based thereon
作者： K. A. Volkov , G. V. Avramenko , V. M. Negrimovskii , E. A. Luk’yanets
DOI: 10.1134/S107036320706028X
关键词: Alkyl 、 Regioselectivity 、 Medicinal chemistry 、 Benzene 、 Organic chemistry 、 Base (chemistry) 、 Nucleophilic substitution 、 Sulfanyl 、 Chemistry 、 Nucleophile 、 Metal 、 General chemistry
摘要: Nucleophilic substitution of chlorine atoms in tetrachlorophthalonitrile by benzene- and alkanethiols the presence a base was studied at different reactant ratios. The is characterized complete regioselectivity: atom position 4 replaced first; next follows replacement 5-chlorine atom. reactions with nucleophiles ratios 1:2 1:4 lead to formation corresponding 3,6-dichloro-4,5-bis[phenyl(alkyl)sulfanyl]- tetrakis[phenyl(alkyl)sulfanyl]phthalonitriles. latter were converted into metal complexes [phenyl-(alkyl)sulfanyl]-substituted phthalocyanines which absorb red near-IR regions electronic spectra.
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sci-hub.se 参考文章(37)
Selami Şaşmaz, Ayşen Ağar, Erbil Ağar, Synthesis and Properties of the Phthalocyanines Containing Eugenol (4-Allyl-2-Methoxyphenol) Turkish Journal of Chemistry. ,vol. 23, pp. 131- 138 ,(1999)
C. C. Leznoff, A. B. P. Lever, Phthalocyanines : properties and applications Wiley. ,(1989)
Alexey V. Smirnov, Igor G. Abramov, Vladimir V. Plakhtinskii, Galina G. Krasovskaya, 4-(1-Benzotriazolyl)-5-nitrophthalonitrile as a highly active substrate in aromatic nucleophilic substitution reactions Mendeleev Communications. ,vol. 12, pp. 72- 74 ,(2002) , 10.1070/MC2002V012N02ABEH001538
Clifford C. Leznoff, Sebastian M. Marcuccio, Shafrira Greenberg, A. B. P. Lever, Kenneth B. Tomer, Metallophthalocyanine dimers incorporating five-atom covalent bridges Canadian Journal of Chemistry. ,vol. 63, pp. 623- 631 ,(1985) , 10.1139/V85-102
Rong Ao, Lothar Kümmerl, Dietrich Haarer, Present limits of data storage using dye molecules in solid matrices Advanced Materials. ,vol. 7, pp. 495- 499 ,(1995) , 10.1002/ADMA.19950070522
Martin K. Casstevens, Marek Samoc, Jiri Pfleger, Paras N. Prasad, Dynamics of third‐order nonlinear optical processes in Langmuir–Blodgett and evaporated films of phthalocyanines Journal of Chemical Physics. ,vol. 92, pp. 2019- 2024 ,(1990) , 10.1063/1.458035
E. A. Makarova, E. V. Dzyuina, E. A. Luk’yanets, Phthalocyanines and related compounds: XLII. Synthesis of phenyl-substituted tetraazachlorins and tetraazabacteriochlorins Russian Journal of General Chemistry. ,vol. 76, pp. 1165- 1169 ,(2006) , 10.1134/S1070363206070280
K.-D. Schiebaum, R. Zhou, S. Knecht, R. Dieing, M. Hanack, W. Göpel, The interaction of transition metal phthalocyanines with organic molecules: a quartz-microbalance study Sensors and Actuators B-chemical. ,vol. 24, pp. 69- 71 ,(1995) , 10.1016/0925-4005(95)85015-5
M. K. Engel, P. Bassoul, L. Bosio, H. Lehmanns, M. Hanacks, J. Simon, Mesomorphic molecular materials. Influence of chain length on the structural properties of octa-alkyl substituted phthalocyanines Liquid Crystals. ,vol. 15, pp. 709- 722 ,(1993) , 10.1080/02678299308036489
A. Lux, G.G. Rozenberg, K. Petritsch, S.C. Moratti, A.B. Holmes, R.H. Friend, A series of novel liquid crystalline octakis(alkylthio)-substituted phthalocyanines Synthetic Metals. ,vol. 102, pp. 1527- 1528 ,(1999) , 10.1016/S0379-6779(98)01149-7