The microwave-assisted synthesis and characterization of novel metal-free and metallophthalocyanines peripherally fused to four 13-membered diazadithia macrocycles

Dyes and Pigments

Volumn 80, Issue 1, 2009, Pages 93-97

  Çelenk, Elif ^a   Kantekin, Halit ^a  

^a KARADENIZ TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Macrocyclic compound; Macrocyclization; Metallophthalocyanine; Mixed donor macrocyclic; Phthalocyanine; Tosylation

Indexed keywords

CHLORINE COMPOUNDS; COMPLEXATION; DYES; ELECTROMAGNETIC WAVES; ETHANOL; MICROWAVES; SYNTHESIS (CHEMICAL);

MACROCYCLIC COMPOUND; MACROCYCLIZATION; METALLOPHTHALOCYANINE; MIXED-DONOR MACROCYCLIC; PHTHALOCYANINE; TOSYLATION;

METALS;

DYE; INORGANIC COMPOUND; IRRADIATION; SYNTHESIS;

EID: 51249097721     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2008.05.006     Document Type: Article

References (30)

1. In: Leznoff C.C., and Lever A.B.P. (Eds). Phthalocyanines. Properties and applications vols. 1-4 (1989), VCH, Cambridge 1993, 1996
2. Hanack M., Heckmann H., and Polley R. In: Schaumann E. (Ed). Methods of organic chemistry (Houben-Weyl) vol. E9d (1998), Georg Thieme Verlag, Stuttgart 717
3. Hanack M., Hees M., Stihler P., Winter G., and Subramanian L.R. In: Skotheim T.E., Elsenbaum R.L., and Reynolds J.R. (Eds). Handbook of conducting polymers (1997) 381
4. Moser F.H., and Thomas A.L. Phthalocyanine compounds (1963), Reinhold Publishing Corporation, New York
5. Wohrle D. Polymer square-planar metal chelates for science and industry. Synthesis, properties and applications. Advances in Polymer Science 50 (1983) Review Article
6. Kobel W., and Hanack M. Bisaxially coordinated (phthalocyaninato)ruthenium(II) compounds. Inorganic Chemistry 25 1 (1986) 103-107
7. Lkahl J., Faulkner L.R., Dwarakanath K., and Tachikawa H. Reversible oxidation and reduction of magnesium phthalocyanine electrodes, electrochemical behaviour and in situ Raman spectroscopy. Journal of the American Chemical Society 108 18 (1986) 5434-5440
8. Ahcar B.N., Fohlen G.M., and Parker J.A. A new solid phase polymerisation - metal phthalocyanine sheet polymer. Journal of Polymer Science Part A Polymer Chemistry 21 2 (1983) 589-597
9. Hanack M., Deger S., and Lange A. Bisaxially coordinated macrocyclic transition metal complexes. Coordination Chemistry Reviews 83 (1988) 115-136
10. Margaron P., Langlois R., Van-lier J.E., and Gaspard S. Photodynamic properties of naphthosulfobenzoporphyrazines, novel asymmetric amphiphilic phthalocyanine derivatives. Journal of Photochemistry and Photobiology B Biology 14 3 (1992) 187-199
11. Leznoff C.C., and Lever A.B.P. Phthalocyanines: properties and application vol. 1 (1989), VCH Publishers, USA p. 16-38
12. Rosa A., and Baerends E.J. Metal-macrocycle interaction in phthalocyanines: density functional calculations of ground and excited state. Inorganic Chemistry 33 (1994) 584-595
13. Takako O, Mustuba I. Japan Patent 05, 133534, P187652e; 1993. Chemical Abstracts 119 (1993) P187652e
14. Kesel D. Milestones in photodynamic therapy (MS82) (1993), SPIE, Belingham, WA
15. In: Loupy A. (Ed). Microwaves in organic synthesis (2002), Wiley VCH, Weinheim
16. Deshayes S., Liagre M., Loupy A., Luche J.L., and Petit A. Microwave activation in phase transfer catalysis. Tetrahedron 55 36 (1999) 10851-10870
17. Loupy A., Petit A., Hamelin J., Texier-Boullet F., Jacquault P., and Mathe D. New solvent free organic synthesis using focused microwaves. Synthesis (Stuttgart) 9 (1998) 1213
18. Bogdal D., Pielichowski J., Penczek P., and Prociak A. Microwave assisted synthesis, crosslinking, and processing of polymeric materials. Advances in Polymer Science 163 (2003) 193-263
19. Perreux L., and Loupy A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 57 45 (2001) 9199-9223
20. Jacob J., Chia L.H.L., and Boey F.Y.C. Thermal and nonthermal interaction of microwave-radiation with materials. Journal of Materials Science 30 21 (1995) 5321-5327
21. Caddick S. Microwave-assisted organic-reactions. Tetrahedron 51 38 (1995) 10403-10432
22. Gök H.Z., Kantekin H., Gök Y., and Herman G. The synthesis and characterization of new metal-free and metallophthalocyanines containing four 27-membered diazaheptathia macrocycles. Dyes and Pigments 75 (2007) 606-611
23. Thompson M.C., and Busch D.H. Reactions of coordinated ligands 9. Utilization of template hypothesis to synthesize macrocyclic ligands in situ. Journal of the American Chemical Society 86 18 (1964) 3651
24. Kantekin H., Celenk E., and Karadeniz H. Synthesis and characterization of new metal-free and metallophthalocyanines containing macrocyclic moieties. Journal of Organometallic Chemistry 693 7 (2008) 1353-1358
25. von Nostrum C.F., Picken S.J., Schouten A.-J., and Nolte R.J.M. Synthesis and supramolecular chemistry of novel liquid-crystalline crown ether-substituted phthalocyanines - toward molecular wires and molecular ionoelectronics. Journal of the American Chemical Society 117 40 (1995) 9957-9965
26. Lever A.B.P. Advances in Inorganic Chemistry Radiochemistry 7 (1965) 27
27. Kantekin H., Deǧirmencioǧlu I., and Gök Y. Synthesis and characterization of a novel diloop macrocycle substituted phthalocyanine. Acta Chemica Scandinavica 53 4 (1999) 247-252
28. Yi{dotless}lmaz I., and Bekaroǧlu O. Synthesis and characterization of novel phthalocyanines with four 16-membered diazadithia macrocycles. Chemische Berichte 129 8 (1996) 967-971
29. Stilman M.J., and Thomson A.J. Assignment of charge-transfer bands in some metal phthalocyanines - evidence for S = 1 state of iron(II) phthalocyanine in solution. Journal of Chemical Society Faraday Transactions II 70 5 (1974) 790-804
30. Reisen A., Zehnder M., and Kaden T.A. Metal-complexes of macrocyclic 24 binüclear complexes. Helvetica Chimica Acta 69 8 (1986) 2074-2080