Novel porphyrazines containing peripherally functionalized macrocyclic (N2O2, N2S2) units: Synthesis and characterization

Dyes and Pigments

Volumn 80, Issue 1, 2009, Pages 187-193

  Bilgin, Ahmet ^a   Ertem, Beytullah ^b   Gök, Yaşar ^c  

^a KOCAELI UNIVERSITY   (Turkey)

^b KARADENIZ TECHNICAL UNIVERSITY   (Turkey)

^c PAMUKKALE UNIVERSITY   (Turkey)

Author keywords

Macrocycles; Magnesium; Maleonitrile; Porphyrazine; Tetraazaporphyrin; Zinc

Indexed keywords

AMINES; BUTENES; CHLORINE COMPOUNDS; COPPER; COPPER COMPOUNDS; DYES; HYDROCARBONS; MAGNESIUM; ZINC; ZINC COMPOUNDS;

MACROCYCLES; MALEONITRILE; PORPHYRAZINE; PORPHYRAZINES; TETRAAZAPORPHYRIN;

OPTICAL DEVICES;

CHEMICAL ANALYSIS; METAL; METAL-COMPLEX DYE; SYNTHESIS;

EID: 51249084968     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2008.07.002     Document Type: Article

References (45)

1. de la Torre G., Claessens C.G., and Torres T. Phthalocyanines: old dyes, new materials. Putting color in nanotechnology. Journal of the Chemical Society, Chemical Communications (2007) 2000-2015
2. Schultz H., Lehmann H., Rein M., and Hanack M. Phthalocyaninatometal and related complexes with special electrical and optical-properties. Structure and Bonding (Berlin) 74 (1991) 41-154
3. Suslick K.S., Rakow N.A., Kosal M.E., and Chou J. The materials chemistry of porphyrins and metalloporphyrins. Journal of Porphyrins and Phthalocyanines 4 (2000) 407-413
4. Collins G.E., Armstrong N.R., Pankow J.W., Oden C., Brina R., Arbour C., et al. Thin-film sensors - the role of defects and impurity sites in controlling sensor response and selectivity. Journal of Vacuum Science and Technology A 11 (1993) 1383-1391
5. Díaz-García M.A., Ledoux I., Duro J.A., Torres T., Agulló-López F., and Zyss J. Third-order nonlinear-optical properties of soluble octasubstituted metallophthalocyanines. Journal of Physical Chemistry 98 (1994) 8761-8764
6. Bonnet R. Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chemical Society Reviews 24 (1995) 19-33
7. Rosenthal I. In: Leznoff C.C., and Lever A.B.P. (Eds). Phthalocyanines: properties and applications vol. 4 (1996), VCH, New York 485-507
8. Giribabu L., Chandrasekharam M., Mohan S.M., Rao Ch.S., Kantam M.L., Reddy M.R., et al. Highly efficient one-pot synthesis of metalloporphyrazines under mild conditions. Synlett (2006) 1604-1606
9. 2 solar cell. Coordination Chemistry Reviews 248 (2004) 1363-1379
10. Koray A.R., Ahsen V., and Bekaroglu O. Preparation of a novel, soluble copper phthalocyanine with crown-ether moieties. Journal of the Chemical Society, Chemical Communications (1986) 932-933
11. van Nostrum C.F., and Nolte R.J.M. Functional supramolecular materials: self-assembly of phthalocyanines and porphyrazines. Journal of the Chemical Society, Chemical Communications (1996) 2385-2392
12. Beall L.S., Mani N.S., White A.J.P., Williams D.J., Barrett A.G.M., and Hoffman B.M. Porphyrazines and norphthalocyanines bearing nitrogen donor pockets: metal sensor properties. Journal of Organic Chemistry 63 (1998) 5806-5817
13. Saǧlam O., and Gül A. Porphyrazines with appending eight crown ethers. Polyhedron 20 (2001) 269
14. 2 by a mixed oxathioether crown. Journal of the Chemical Society, Chemical Communications (1994) 1751-1752
15. van Nostrum C.F., Benneker F.B.G., Brussaard H., Kooijman H., Veldman N., Spek A.L., et al. Dithiacrown ether substituted porphyrazines: synthesis, single-crystal structure, and control of aggregation in solution by complexation of transition-metal ions. Inorganic Chemistry 35 (1996) 959-969
16. Pullen A.E., Faulmann C., and Cassoux P. Synthesis and investigation of chalcogen atom substituted dinitriles and porphyrazines. European Journal of Inorganic Chemistry (1999) 269-276
17. Sibert J.W., Lange S.J., Barrett A.G.M., and Hoffman B.M. Synthesis and coordination chemistry of unsymmetrical tetraazaporphyrins containing single oxathia- and thiacrown substituents. Tetrahedron 56 (2000) 7371-7377
18. Karadeniz H., Gök Y., and Kantekin H. The synthesis and characterization of new metal-free and metalloporphyrazine containing macrobicyclic moieties. Dyes and Pigments 75 (2007) 498-504
19. Che C.M., Butler L.G., Grunthaner P.J., and Gray H.B. Chemistry and spectroscopy of binuclear platinum diphosphite complexes. Inorganic Chemistry 24 (1985) 4662-4665
20. Gupta G.P., Lang G., Koch C.A., Wang B., Scheidt W.R., and Reed C.A. Mossbauer and magnetic-susceptibility investigation of a ferromagnetically coupled iron(III) porphyrin-dicopper(II) system with imidazolate bridging ligands. Inorganic Chemistry 29 (1990) 4234-4239
21. 2O. Inorganic Chemistry 25 (1986) 957-964
22. 4-). Journal of the American Chemical Society 103 (1981) 7796-7797
23. Sharp P.R., Raymond K.N., Smart J.C., and McKinney R.J. Structure and bonding of bis(fulvalene)dinickel. Journal of the American Chemical Society 103 (1981) 753-757
24. Gibney B.R., Kessissoglou D.P., Kampf J.W., and Pecararo V.L. Copper(II) 12-metallacrown-4: synthesis, structure, ligand variability, and solution dynamics in the 12-MC-4 structural motif. Inorganic Chemistry 33 (1994) 4840-4849
25. Bilgin A., Ertem B., and Gök Y. Synthesis and characterization of novel metal free and metallophthalocyanines diazadioxamacrocycles. Supramolecular Chemistry 17 (2005) 277-281
26. Bilgin A., and Gök Y. Synthesis and characterization of novel metal-free phthalocyanines substituted with four diazadithiatetraoxa or diazahexaoxamacrobicyclic moieties. Tetrahedron Letters 43 (2002) 5343-5347
27. Bilgin A., Ertem B., and Gök Y. Synthesis and characterization of novel metal-free phthalocyanines containing four cylindrical or spherical macrotricyclic moieties. Tetrahedron Letters 43 (2003) 6937-6941
28. Bilgin A., Ertem B., and Gök Y. The synthesis and properties of new metal free and metallophthalocyanines containing four diloop macrocyclic moieties. Supramolecular Chemistry 18 (2006) 361-369
29. Bilgin A., Ertem B., and Gök Y. Highly organosoluble metal-free phthalocyanines and metallophthalocyanines: synthesis and characterization. European Journal of Inorganic Chemistry (2007) 1703-1712
30. Ertem B., Bilgin A., Gök Y., and Kantekin H. The synthesis and characterization of novel metal-free and metallophthalocyanines bearing eight 16-membered macrocycles. Dyes and Pigments 77 (2008) 537-544
31. Gök Y., Ocak U., and Şentürk H.B. First example of a vic-dioxime and its homo- and heteropentanuclear complexes containing a macrobicyclic moiety. New Journal of Chemistry 25 (2001) 364-368
32. 2. Inorganic Chemistry 32 (1993) 1297-1300
33. Perin D.D., and Armarego W.L.F. Purification of laboratory chemicals. 2nd ed. (1989), Pergamon Press, Oxford
34. Linstead R.P., and Whalley M. Conjugated macrocycles. 22. Tetraazaporphin and its metallic derivatives. Journal of the Chemical Society (1952) 4839-4846
35. Hanack M., Heckmann H., and Polley R. Methods of organic chemistry (1998), Georg ThiemeVerlag, Stuttgart Additional Supplementary Volume. p. 776
36. van 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 (1995) 9957-9965
37. Bilgin A., Ertem B., and Gök Y. The synthesis and characterization of a new metal-free phthalocyanine substituted with four diloop macrocyclic moieties. Tetrahedron Letters 44 (2003) 3829-3833
38. Liu W., Lee C.-H., Chan H.-S., Mak T.C.W., and Ng D.K.P. Synthesis, spectroscopic properties, and structure of [tetrakis(2,4-dimethyl-3-pentyoxy)phthalocyaninato]metal complexes. European Journal of Inorganic Chemistry (2004) 286-292
39. Hanack M., Meng D.Y., Beck A., Sommerauer M., and Subramanian L.R. Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II). Journal of the Chemical Society, Chemical Communications (1993) 58-60
40. Hanack M., Schmid G., and Sommerauer M. Chromatographic-separation of the 4 possible structural isomers of a tetrasubstituted phthalocyanine - tetrakis(2-ethylhexyloxy)phthalocyaninatonickel(II). Angewandte Chemie. International Edition in English 32 (1993) 1422-1424
41. Michel S.L., Baum S., Barrett A.G.M., and Hoffman B.M. In: Karlin K.D. (Ed). Progress in inorganic chemistry vol. 50 (2001), Wiley, New York 473
42. Gonca E., and Gül A. Magnesium porphyrazinate with eight triphenylphosphonium moieties attached through (2-sulfanyl-ethoxycarbonyl-2-propyl) bridges. Inorganic Chemistry Communications 8 (2005) 343-346
43. Keskin B., Köseoǧlu Y., Avci{dotless}ata U., and Gül A. Synthesis and EPR studies of porphyrazines with bulky substituents. Polyhedron 27 (2008) 1155-1160
44. Garrido Montalban A., Meunier H.G., Ostler R.B., Barrett A.G.M., Hoffman B.M., and Rumbles G. Photoperoxidation of a diamino zinc porphyrazine to the seco-zinc porphyrazine: suicide or murder?. Journal of Physical Chemistry A 103 (1999) 4352-4358
45. Cook A.S., Williams D.B.G., White A.J.P., Williams D.J., Lange S.J., Barrett A.G.M., et al. Enantiomerically pure "winged" spirane porphyrazinoctaols. Angewandte Chemie. International Edition in English 36 (1997) 760-761