BibTex RIS Kaynak Göster

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

Yıl 2016, Cilt: 17 Sayı: 2, 327 - 336, 14.07.2016
https://doi.org/10.18038/btda.54345

Öz

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.

Kaynakça

  • 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

Yıl 2016, Cilt: 17 Sayı: 2, 327 - 336, 14.07.2016
https://doi.org/10.18038/btda.54345

Öz

Kaynakça

  • 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.
Toplam 26 adet kaynakça vardır.

Ayrıntılar

Bölüm Araştırma Makalesi
Yazarlar

Meltem Betül Sağlam Bu kişi benim

Yayımlanma Tarihi 14 Temmuz 2016
Yayımlandığı Sayı Yıl 2016 Cilt: 17 Sayı: 2

Kaynak Göster

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. AUBTD-A. Ağustos 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, sy. 2 (Ağustos 2016): 327-36. https://doi.org/10.18038/btda.54345.
EndNote Sağlam MB (01 Ağustos 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”, AUBTD-A, c. 17, sy. 2, ss. 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 (Ağustos 2016), 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. AUBTD-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, c. 17, sy. 2, 2016, ss. 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. AUBTD-A. 2016;17(2):327-36.