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

Year 2016, Volume: 17 Issue: 2, 327 - 336, 14.07.2016

Meltem Betül Sağlam

https://doi.org/10.18038/btda.54345

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

References

  • Gregory P. High Technology Applications of Organic Colorants, Plenum Press: New York, 1991.
  • Lezznoff CC, Lever ABP. Phthalocyanines properties and applications, Springer, Berlin, vol. 2, 1993.
  • Rosenthal I. Phthalocyanines as photodynamic sensitizers. Photochem Photobiol 1991; 53(6): 859- 870.
  • Keown NB. Mc Editor, Phthalocyanine Materials. Cambridge: Cambridge University Press,1998.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Deshayes S, Liagre M, LoupyA, Luche JL, Petit A. Microwave activation in phase transfer catalysis. Tetrahedron 1999; 55(36): 10851-10870.
  • 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.
  • 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.
  • Aijian W, Lingliang L, Chi Z. Synthesis of unsymmetrical phthalocyanines: a brief overview. Tetrahedron 2012; 68(11): 2433-2451.
  • 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.
  • 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.
  • Young G. J, Onyebuagu W. Synthesis and characterization of di-disubstituted phthalocyanines. J Org Chem 1990; 55: 2155-2159.
  • Perrin DD, Armarego WLF, Perrin DR. Purification of Laboratory Chemicals, 2nd ed., Pergamon Press: New York, 1989.
  • Snow AW, Griffith JR. Syntheses and Characterization of Heteroatom-Bridged Metal free Phthalocyanine Network Polymers and Model Compounds. Macromolecules 1984; 17: 1614-1624.
  • 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.
  • 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.
  • 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.
  • Martin AE, Bulkowski JE. General synthetic route to hexaamine macrocycles. J. Org Chem 1982; 47(3): 415-418.
  • Lehn JM. Dinuclear cryptates: dimetallic macropolycyclic inclusion complexes: concepts-design- prospects. Pure Appl Chem 1980; 52(1): 2441-2459.
  • 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.
  • Jiang JZ. Advances in functional phthalocyanine materials, Structure and Bonding, Heidlberg: Springer –Verlag, 2010, 135.

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

Year 2016, Volume: 17 Issue: 2, 327 - 336, 14.07.2016

Meltem Betül Sağlam

https://doi.org/10.18038/btda.54345

Abstract

References

  • Gregory P. High Technology Applications of Organic Colorants, Plenum Press: New York, 1991.
  • Lezznoff CC, Lever ABP. Phthalocyanines properties and applications, Springer, Berlin, vol. 2, 1993.
  • Rosenthal I. Phthalocyanines as photodynamic sensitizers. Photochem Photobiol 1991; 53(6): 859- 870.
  • Keown NB. Mc Editor, Phthalocyanine Materials. Cambridge: Cambridge University Press,1998.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Deshayes S, Liagre M, LoupyA, Luche JL, Petit A. Microwave activation in phase transfer catalysis. Tetrahedron 1999; 55(36): 10851-10870.
  • 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.
  • 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.
  • Aijian W, Lingliang L, Chi Z. Synthesis of unsymmetrical phthalocyanines: a brief overview. Tetrahedron 2012; 68(11): 2433-2451.
  • 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.
  • 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.
  • Young G. J, Onyebuagu W. Synthesis and characterization of di-disubstituted phthalocyanines. J Org Chem 1990; 55: 2155-2159.
  • Perrin DD, Armarego WLF, Perrin DR. Purification of Laboratory Chemicals, 2nd ed., Pergamon Press: New York, 1989.
  • Snow AW, Griffith JR. Syntheses and Characterization of Heteroatom-Bridged Metal free Phthalocyanine Network Polymers and Model Compounds. Macromolecules 1984; 17: 1614-1624.
  • 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.
  • 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.
  • 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.
  • Martin AE, Bulkowski JE. General synthetic route to hexaamine macrocycles. J. Org Chem 1982; 47(3): 415-418.
  • Lehn JM. Dinuclear cryptates: dimetallic macropolycyclic inclusion complexes: concepts-design- prospects. Pure Appl Chem 1980; 52(1): 2441-2459.
  • 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.
  • Jiang JZ. Advances in functional phthalocyanine materials, Structure and Bonding, Heidlberg: Springer –Verlag, 2010, 135.
There are 26 citations in total.

Details

Journal Section Articles
Authors

Meltem Betül Sağlam This is me

Publication Date July 14, 2016
Published in Issue Year 2016 Volume: 17 Issue: 2

Cite

APA Sağlam, M. B. (2016). Microwave-assisted synthesis and characterization of a new metal-free phthalocyanine and four metallophthalocyanines bearing 9-flourene methanol moities. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 17(2), 327-336. https://doi.org/10.18038/btda.54345
AMA Sağlam MB. Microwave-assisted synthesis and characterization of a new metal-free phthalocyanine and four metallophthalocyanines bearing 9-flourene methanol moities. AUJST-A. August 2016;17(2):327-336. doi:10.18038/btda.54345
Chicago Sağlam, Meltem Betül. “Microwave-Assisted Synthesis and Characterization of a New Metal-Free Phthalocyanine and Four Metallophthalocyanines Bearing 9-Flourene Methanol Moities”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17, no. 2 (August 2016): 327-36. https://doi.org/10.18038/btda.54345.
EndNote Sağlam MB (August 1, 2016) Microwave-assisted synthesis and characterization of a new metal-free phthalocyanine and four metallophthalocyanines bearing 9-flourene methanol moities. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17 2 327–336.
IEEE M. B. Sağlam, “Microwave-assisted synthesis and characterization of a new metal-free phthalocyanine and four metallophthalocyanines bearing 9-flourene methanol moities”, AUJST-A, vol. 17, no. 2, pp. 327–336, 2016, doi: 10.18038/btda.54345.
ISNAD Sağlam, Meltem Betül. “Microwave-Assisted Synthesis and Characterization of a New Metal-Free Phthalocyanine and Four Metallophthalocyanines Bearing 9-Flourene Methanol Moities”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 17/2 (August2016), 327-336. https://doi.org/10.18038/btda.54345.
JAMA Sağlam MB. Microwave-assisted synthesis and characterization of a new metal-free phthalocyanine and four metallophthalocyanines bearing 9-flourene methanol moities. AUJST-A. 2016;17:327–336.
MLA Sağlam, Meltem Betül. “Microwave-Assisted Synthesis and Characterization of a New Metal-Free Phthalocyanine and Four Metallophthalocyanines Bearing 9-Flourene Methanol Moities”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, vol. 17, no. 2, 2016, pp. 327-36, doi:10.18038/btda.54345.
Vancouver Sağlam MB. Microwave-assisted synthesis and characterization of a new metal-free phthalocyanine and four metallophthalocyanines bearing 9-flourene methanol moities. AUJST-A. 2016;17(2):327-36.
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