Synthesis of sulfonamide-substituted phthalocyanines

被引:13
作者
Carvalho, Eliana F. A. [1 ]
Calvete, Mario J. F. [1 ]
Tome, Augusto C. [1 ]
Cavaleiro, Jose A. S. [1 ]
机构
[1] Univ Aveiro, Dept Chem, QOPNA, P-3810193 Aveiro, Portugal
关键词
Phthalocyanines; Phthalonitriles; Chlorosulfonation; Sulfonamides; ZINC PHTHALOCYANINE; PHOTOSENSITIZERS; EFFICACY; COBALT; COPPER;
D O I
10.1016/j.tetlet.2009.09.128
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and characterization of new phthalocyanines bearing eight N-alkyl or N-aryl sulfonamide groups is described. The synthetic route involves the chorosulfonation of 4,5-diphenoxyphthalonitrile with chlorosulfonic acid and reaction of the resulting 4,5-bis(p-chlorosulfonylphenoxy)phthalonitrile with amines. The sulfonamide-substituted phthalonitriles are then cyclotetramerized to yield the title Compounds in good yields (50-83%). (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6882 / 6885
页数:4
相关论文
共 36 条
[1]   Pd-catalyzed Heck reaction for the synthesis of isomeric metallo tetravinylsulfo phthalocyanines and their photosensitizing properties [J].
Ali, Hasrat ;
Cauchon, Nicole ;
van Lier, Johan E. .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2009, 8 (06) :868-874
[2]   The first example of anomeric glycoconjugation to phthalocyanines [J].
Alvarez-Mico, X ;
Calvete, MJF ;
Hanack, M ;
Ziegler, T .
TETRAHEDRON LETTERS, 2006, 47 (19) :3283-3286
[3]  
ANA RM, 2009, CARBOHYD RES, V344, P507
[4]   Investigation of gas-sensing properties of copper phthalocyanine films [J].
Basova, T. ;
Tsargorodskaya, A. ;
Nabok, A. ;
Hassan, A. K. ;
Gurek, A. G. ;
Gumus, G. ;
Ahsen, V. .
MATERIALS SCIENCE & ENGINEERING C-BIOMIMETIC AND SUPRAMOLECULAR SYSTEMS, 2009, 29 (03) :814-818
[5]   Comparative Gas Sensing in Cobalt, Nickel, Copper, Zinc, and Metal-Free Phthalocyanine Chemiresistors [J].
Bohrer, Forest I. ;
Colesniuc, Corneliu N. ;
Park, Jeongwon ;
Ruidiaz, Manuel E. ;
Schuller, Ivan K. ;
Kummel, Andrew C. ;
Trogler, William C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :478-485
[6]   Synthesis of a bisphthalocyanine and its nonlinear optical properties [J].
Calvete, MJF ;
Dini, D ;
Flom, SR ;
Hanack, M ;
Pong, RGS ;
Shirk, JS .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (16) :3499-3509
[7]   In vitro photosensitizing efficacy of cationic phthalocyanine derivatives against C.albicans:: effect of serum albumins [J].
Chiti, G ;
Dei, D ;
Fantetti, L ;
Roncucci, G .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2005, 9 (07) :463-469
[8]   Glycosylated zinc(II) phthalocyanines as efficient photosensitisers for photodynamic therapy.: Synthesis, photophysical properties and in vitro photodynamic activity [J].
Choi, Chi-Fung ;
Huang, Jian-Dong ;
Lo, Pui-Chi ;
Fong, Wing-Ping ;
Ng, Dennis K. P. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (12) :2173-2181
[9]   Structure-Function Relationships in Unsymmetrical Zinc Phthalocyanines for Dye-Sensitized Solar Cells [J].
Cid, Juan-Jose ;
Garcia-Iglesias, Miguel ;
Yum, Jun-Ho ;
Forneli, Amparo ;
Albero, Josep ;
Martinez-Ferrero, Eugenia ;
Vazquez, Purificacion ;
Graetzel, Michael ;
Nazeeruddin, Mohammad K. ;
Palomares, Emilio ;
Torres, Tomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (20) :5130-5137
[10]   Synthesis, characterization and catalytic activity of cobalt phthalocyanine tetrasulphonamide in sweetening of LPG [J].
Das, Gautam ;
Sain, Bir ;
Kumar, Sunil ;
Garg, M. O. ;
Dhar, G. Murali .
CATALYSIS TODAY, 2009, 141 (1-2) :152-156