Microwave-assisted synthesis and characterization of a new metal-free phthalocyanine and four metallophthalocyanines bearing 9-flourene methanol moities

Abstract

The new metal-free phthalocyanine 2 and metallophtalocyanines 3, 4, 5, 6 containing four groups on peripheral positions have been synthesized by cyclotetramerization reaction of a nitrile compound, having three reaction steps. These new complexes were demonstrated using   spectroscopic data and elemental analysis.

Keywords

• Nitrile, Metallophthalocyanine, Cyclotetramerization, Macrocyclic

MICROWAVE-ASSISTED SYNTHESIS AND CHARACTERIZATION OF A NEW METAL- FREE PHTHALOCYANINE AND FOUR METALLOPHTHALOCYANINES BEARING 9- FLOURENE METHANOL MOITIES

Abstract

References

1. Gregory P. High Technology Applications of Organic Colorants, Plenum Press: New York, 1991.
2. Lezznoff CC, Lever ABP. Phthalocyanines properties and applications, Springer, Berlin, vol. 2, 1993.
3. Rosenthal I. Phthalocyanines as photodynamic sensitizers. Photochem Photobiol 1991; 53(6): 859- 870.
4. Keown NB. Mc Editor, Phthalocyanine Materials. Cambridge: Cambridge University Press,1998.
5. Scalise A, Durantimi EN. Synthesis, properties, and photodynamic inactivation of Escherichia coli using a cationic and a noncharged Zn(II) pyridyloxyphthalocyanine derivatives. Bioorg Med Chem 2005; 13(8): 3037-3045.
6. Sakamoto K, Kato T, Ohno-Okumura E, Watanabe M, Cook MJ. Synthesis of novel cationic amphiphilic phthalocyanine derivatives for next generation photosensitizer using photodynamic therapy of cancer. Dyes and Pigments 2005; 64: 63-71.
7. Newton MI, Starke TKH, Willis MR, McHale G. NO2 detection at room temperature with copper phthalocyanine thin film devices. Sens Actuators B 2000; 67(3), 307-311.
8. Kobayashi N, Nevin WA Electrocatalytic Reduction of Oxygen Using Water-Soluble Iron and Cobalt Phthalocyanines and Porphyrins. Appl Organom Chem 1996; 10(8): 579-590.

9. Wöhrle D, Gitzel J, Krawezyk G, Tsuchida E, Ohno H, Nishisaka TJ. Synthesis, Redox Behavior, Sensitizer Activity, and Oxygen Transfer of Covalently Bound Polymeric. Porphyrins Macromol Sci Chem A. 1988; 25(10-11): 1227-1254.
10. Hanack M, Lang M. Conducting Stacked Metallophthalocyanines and Related Compounds Adv Mater 1994; 6(11): 819-833. [11] Loupy A, editor. Microwaves in Organic Synthesis, Weinheim: Wiley VCH, 2002.
11. Deshayes S, Liagre M, LoupyA, Luche JL, Petit A. Microwave activation in phase transfer catalysis. Tetrahedron 1999; 55(36): 10851-10870.
12. Loupy A, Petit A, Hamelin J, Texier-Boullet F, Jacquault P, Mathe D. New Solvent-Free Organic Synthesis Using Focused Microwaves. Synthesis (Stuttgart) 1998; 9: 1213-14.
13. Bogdal D, Pielichowski J, Penczek P, Prociak A, Microwave Assisted Synthesis, Crosslinking, and Processing of Polymeric Materials. Advances in Polymer Science 2003; 163: 193-263.
14. Aijian W, Lingliang L, Chi Z. Synthesis of unsymmetrical phthalocyanines: a brief overview. Tetrahedron 2012; 68(11): 2433-2451.
15. Bıyıklıoğlu Z, Kantekin H, Özil M. Microwave-assisted synthesis and characterization of novel metal-free and metallophthalocyanines containing four14-membered tetraaza macrocycles. J Organomet Chem 2007 ; 692 : 2436-2440.
16. Bıyıklıoğlu Z, Kantekin H. Microwave assisted synthesis and characterization of novel metal-free and metallophthalocyanines containing four pyridyl groups. TransMet Chem 2007; 32(7):851-859.
17. Young G. J, Onyebuagu W. Synthesis and characterization of di-disubstituted phthalocyanines. J Org Chem 1990; 55: 2155-2159.
18. Perrin DD, Armarego WLF, Perrin DR. Purification of Laboratory Chemicals, 2nd ed., Pergamon Press: New York, 1989.
19. Snow AW, Griffith JR. Syntheses and Characterization of Heteroatom-Bridged Metal free Phthalocyanine Network Polymers and Model Compounds. Macromolecules 1984; 17: 1614-1624.
20. Von Nostrum CF, Picken SJ, Schouten AJ, Nolte RJM. Synthesis and supramolecular chemistry of novel liquid crystalline crown ether substituted phthalocyanines: towards molecular wires and molecular ionoelectronics. Journal of the American Chemical Society 1995; 117: 9957-9960.
21. Motekaitis RJ, Martell AE, Dietrich B, Lehn JM. Anion binding in macrobicyclic metal cryptate complexes: copper(II)-BISTREN. Inorg Chem 1984; 23(11): 1588-1591.
22. Agnus Y, Louis R, Gisselbrecht JP, Weiss R. Dicopper(II) chloro and azido inclusion complexes of the [24-ane-N2S4] binucleating macrocycle. Synthesis, crystal and molecular structures, and spectral, magnetic, and electrochemical properties. J Am Chem Soc 1984; 106(1): 93-102.
23. Martin AE, Bulkowski JE. General synthetic route to hexaamine macrocycles. J. Org Chem 1982; 47(3): 415-418.
24. Lehn JM. Dinuclear cryptates: dimetallic macropolycyclic inclusion complexes: concepts-design- prospects. Pure Appl Chem 1980; 52(1): 2441-2459.
25. Reisen A, Zehnder M, Kaden TA. Metal complexes of macrocyclic ligands. Part XXIV. Binuclear complexes with tetraazamacrocycle-N,N′,N″,N‴-tetraacetic acids Helvetica Chimica Acta 1986; 69(8): 2074-2080.
26. Jiang JZ. Advances in functional phthalocyanine materials, Structure and Bonding, Heidlberg: Springer –Verlag, 2010, 135.