The synthesis and characterization of new metal-free and metalloporphyrazine containing macrobicyclic moieties

Dyes and Pigments

Volumn 75, Issue 2, 2007, Pages 498-504

  Karadeniz, Hülya ^a   Gök, Yaşar ^b   Kantekin, Halit ^a  

^a KARADENIZ TECHNICAL UNIVERSITY   (Turkey)

^b PAMUKKALE UNIVERSITY   (Turkey)

Author keywords

Metal free porphyrazine; Metalloporphyrazine; Mixed donor macrobicycle; Template effect

Indexed keywords

CHARACTERIZATION; CHEMICAL ANALYSIS; INFRARED SPECTROMETERS; MASS SPECTROMETRY; MICROANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY; SYNTHESIS (CHEMICAL); ULTRAVIOLET VISIBLE SPECTROSCOPY;

METAL-FREE PORPHYRAZINE; METALLOPORPHYRAZINE; MIXED-DONOR MACROBICYCLE;

PIGMENTS;

INORGANIC COMPOUND; MAGNETIC RESONANCE IMAGING; PIGMENT; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 34248195913     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2006.06.027     Document Type: Article

References (47)

1. Leznoff C.C., and Lever A.B.P. Phthalocyanines: properties and applications vols. 1-4 (1989-1996), VCH, New York
2. Moser F.H., and Thomas A.L. The phthalocyanines vols. 1 and 2 (1983), CRC Press, Boca Rotan, Florida
3. McKeown N.B. Phthalocyanine materials: synthesis, structure and function (1998), Cambridge University Press, Cambridge
4. Kadish K.M., Smith K.M., and Guilard R. The porphyrin handbook vols. 15-20 (2003), Academic Press, New York
5. Hanack M., and Lang M. Conducting stacket metallophthalocyanines and related compounds. Adv Mater 6 (1994) 819-833
6. Bonnett R. Photosensitizers of the porphyrin and phthalocyanines series for photodynamic therapy. Chem Soc Rev (1995) 19-34
7. Collins G.E., Armstrong N.R., Pankow J.M., Oden C., Brina R., Arbour C., et al. J Vac Sci Technol A 11 (1993) 1383-1391
8. Piechocki C., Simon J., Skoulios A., Guillon D., and Weber P. Annelides.7. Discotic mesophases obtained from substituted metallophthalocyanines. Toward liquid crystalline one-dimensional conductors. J Am Chem Soc 104 (1982) 5245-5247
9. Diaz-Garcia M.A., Ledoux I., Duro J.A., Torres T., Agullo-Lopez F., and Zyss J. Third-order nonlinear optical properties of soluble octasubstituted metallophthalocyanines. Phys Chem 98 (1994) 8761-8764
10. Beall L.S., Mani N.S., White A.J.P., Williams D.J., Barrett A.G.M., and Hoffman B.M. J Org Chem 63 (1998) 5806-5817
11. Donzello M.P., Ou Z., Monacelli F., Ricciardi G., Rizzoli C., Ercolani C., et al. Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings. 1. Tetra-kis-2,3-[5,6-di(2-pyridyl)pyrazino]porphyrazine: a new macrocycle with remarkable electron-deficient properties. Inorg Chem 43 (2004) 8626-8636
12. Stuzhin P.A., and Ercolani C. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The porphyrin handbook vol. 15 (2003), Academic Press 263
13. I complex with coordination in the meso pocket. Angew Chem Int Ed Engl 34 (1995) 2020-2022
14. Lange S.J., Sibert J.W., Barret A.G., and Hoffman B.M. Synthesis and coordination chemistry of unsymmetrical tetraazaporphyrins containing single oxathia- and thiacrown substituents. Tetrahedron 56 (2000) 7371-7377
15. Wang C., Bryce M.R., Batsanov A.S., and Howard J.A.K. Synthesis and pyrazinoporphyrazine derivatives functionalised with tetrathiafulvalene (TTF) units: X-ray crystal structures of two related TTF cyclophanes and two bis(1,3-dithiole-2-thione) intermediates. Chem Eur J 3 (1997) 1679-1690
16. Michel S.L.J., Barrett A.G.M., and Hoffman B.M. Peripheral metal-ion binding to tris(thia-oxacrown)porphyrazines. Inorg Chem 42 (2003) 814-820
17. van Nostrum C.F., Benneker F.B.G., Brussaard H., Kooijman H., Veldman N., Spek A.L., et al. Dithiacrown ether substituted porphyrazines: synthesis. Inorg Chem 35 (1996) 959-969
18. Lehn J.-M., Dietrich B., and Sauvage J.P. Cryptates-XI: complexes macrobicycliques, formation, structure, properties. Tetrahedron 29 (1973) 1647-1658
19. Lehn J.-M. Supramolecular chemistry (1995), VCH, Weinheim p. 114-43
20. Bilgin A., Ertem B., and Gök Y. The synthesis and characterization of new metal-free phthalocyanine substituted with four diloopmacrocyclic moieties. Tetrahedron Lett 44 (2003) 3829-3833
21. Cunningham J.A., and Sievers R.E. Structure of a novel dimer formed by coupling metal macrocycles. J Am Chem Soc 95 (1973) 7183-7185
22. Comba P., and Hilfenhaus P. One-step template synthesis and solution structures of bis(macrocyclic)octaamine dicopper(II) complexes. J Chem Soc Dalton Trans (1995) 3269-3274
23. Michel S.L.J., Baum S., Barrett A.G.M., and Hoffman B.M. Peripherally functionalized porphyrazines: novel metallomacrocycles with broad, untrapped potential. Prog Inorg Chem 50 (2001) 473-590
24. Graf E., and Lehn J.-M. Cryptates. XVII. Synthesis and cryptate complexes of a spheroidal macrotricyclic ligand with octahedrotetrahedral coordination. J Am Chem Soc 97 (1975) 5022-5024
25. Bilgin A., and Gök Y. Synthesis and characterization of novel metal-free phthalocyanines containing macrobicyclic moieties. Tetrahedron Lett 43 (2002) 5343-5347
26. Davison A., and Holm R.H. Metal complexes derived from cis-1,2-dicyano-1,2-ethylenedithiolate and bis(trifluoromethyl)-1,2-dithiene. Inorg Synth 6 (1967) 8-9
27. Bahr G., and Schleitzer G. Di{dotless}e kondensi{dotless}erende spontan-entschwefelung von salzen und ester der cylan-dithioameisensaure freie cylan-dihioamei{dotless}sensaure. Chem Ber 90 (1957) 438-443
28. Kantekin H., Ocak U., Gök Y., and Alp H. Synthesis and characterization of new (E,E)dioxime and its homo and heterotrinuclear complexes containing dioxadithiadiaza macrobicycle moiety. Polyhedron 21 (2002) 1865-1870
29. Crossley R., Goolamali Z., Gosper J.J., and Sammes P.G. Synthesis and spectral properties of new fluorescent probes for potassium. J Chem Soc Perkin Trans 2 (1994) 513-520
30. Gatto V.J., and Gökel G.W. Syntheses of calcium-selective, substituted diaza-crown ethers: a novel, one-step formation of bibracchial lariat ethers (BİBLES). J Am Chem Soc 106 (1984) 8240-8244
31. Linstead R.P., and Whalley M. Conjugated macrocycles. Part XXII. Tetraazaporphin and its metallic derivatives. J Chem Soc (1952) 4839-4844
32. Yi{dotless}ldi{dotless}z S.Z., and Gök Y. Synthesis and characterization of metal-free and metallophthalocyanines containing four 17-membered dioxa-triazamacrocycles. New J Chem (1998) 1365-1369
33. Saǧlam O., and Gül A. Porphyrazines with appending eight crown ethers. Polyhedron 20 (2001) 269-275
34. Pullen A.E., Faulman C., and Cassoux P. Synthesis and investigation of chalcogen atom substituted dinitriles and porphyrazines. Eur J Inorg Chem (1999) 269
35. Gonca E., Köseoǧlu Y., Aktaş B., and Gül A. Octakis(1-naphthylmethylthio) substituted porphyrazine derivatives. Polyhedron 23 (2004) 1845-1849
36. Akkuş H., and Gül A. Octakis(ferrocene)-substituted porphyrazine. Transition Met Chem 26 (2001) 689
37. Yi{dotless}lmaz I., and Bekaroǧlu O. Synthesis and characterization of novel phthalocyanines with four 16-membered diazadithia macrocycles. Chem Ber 129 (1996) 967-971
38. Sari{dotless}gül S., and Bekaroǧlu O. Synthesis and properties of a phthalocyaninatocopper(II) complex symmetrically substituted with eight crown ethers. Chem Ber 122 (1989) 291-292
39. Lee S., White J.P.A., Williams D.J., Barrett A.G.M., and Hoffman B.M. Synthesis of near absorbing/emitting porphyrazine derivatives with tunable solubility. J Org Chem 66 (2001) 461-465
40. van Nastrum C.F., and Nolte R.J.M. Functional supramolecular materials: self-assembly of phthalocyanines and porphyrazines. Chem Commun (1996) 2385-2386
41. Sakellariou E.G., Montalban A.G., Beall S.C., Henderson D., Meunier H.G., Phillips D., et al. Novel peripherally functionalzed seco-porphyrazines: synthesis, characterization and spectroscopic evaluation. Tetrahedron 59 (2003) 9083-9090
42. Nie H., Barrett A.G.M., and Hoffman B.M. Porphyrazinehexamines and dinitroporphyrazines: synthesis, characterization, and complementary electrochemistry. J Org Chem 64 (1999) 6791-6796
43. Doppelt P., and Huille S. New J Chem 14 (1990) 607-609
44. 8 complex. J Am Chem Soc 112 (1990) 7408-7410
45. Bilgin A, Gök Y. Synthesis and characterization of new metal-free and metallophthalocyanines containing macrobicyclic moieties. Supramol Chem, in press.
46. Bilgin A., Ertem B., and Gök Y. Synthesis and characterization of new metal-free and metallophthalocyanines containing spherical or cylindrical macrotricyclic moieties. Polyhedron 24 (2005) 1117-1124
47. Perin D.D., and Armarego W.L.F. Purification of laboratory chemicals (1988), Pergamon Press, Oxford