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Year 2018, Volume: 5 Issue: 1, 7 - 12, 28.03.2018
https://doi.org/10.17350/HJSE19030000071

Abstract

References

  • Akçay HT, Çoruh U, Bayrak R, Menteşe E, Vazquez Lopez EM. A spectroscopic study on new phthalonitrile derivative and its computational background: 4-[(4,5-Diphenyl- 4H-1,2,4-triazol-3-yl)sulfanyl]benzene-phthalonitrile. Journal of Molecular Structure. 1127 (2017) 539-548.
  • Khanmohammadi H, Abnosi MH, Hosseinzadeh A, Erfantalab M. Synthesis, biological and computational study of new Schiff base hydrazones bearing 3-(4-pyridine)-5- mercapto-1,2,4-triazole moiety. Spectrochim. Acta A 71 (2008) 1474-1480.
  • Li Z, Gu Z, Yin K, Zhang R, Deng Q, Xiang J. Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified D-glucopyranosyl residues and their antiproliferative activities. Eur. J. Med. Chem. 44 (2009) 4716-4720.
  • Bagihalli GB, Avaji PG, Patil SA, Badami PS. Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Eur. J. Med. Chem. 43 (2008) 2639-2649.
  • Ferrer S, Haasnoot JG, Reedijk J, Muller E, Cingi MB, Lanfranchi M, Manotti AM, Ribas LJ. Trinuclear N,N-bridged copper(II) complexes involving a Cu3OH core: [Cu-3(mu(3)- OH)L(3)A(H2O)(2)]A center dot(H2O)(x) {L=3-acetylamino- 1,2,4-triazolate; a = CF3SO3, NO3, ClO4; x = 0, 2} synthesis, X-ray structures, spectroscopy, and magnetic properties. Inorg. Chem. 39 (2000) 1859-1867.
  • Karaca H, Sezer S, Özalp-Yaman Ş, Tanyeli C. Concise synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines having triazole functionality, Polyhedron. 72 (2014) 147-156.
  • Nas A, Fandaklı S, Kantekin H, Demirbaş A, Durmuş M. Novel organosoluble metal-free and metallophthalocyanines bearing triazole moieties: Microwave assisted synthesis and determination of photophysical and photochemical properties. Dyes and Pigments. 95 (2012) 8-17.
  • Demirbaş Ü, Kobak RZU, Akçay HT, Ünlüer D, Koca A, Çelik F, Kantekin H. Synthesis, characterization, electrochemical and spectroelectrochemical properties of novel peripherally tetra-1,2,4-triazole substituted phthalocyanines. Synthetic Metals. 215 (2016) 68-76.
  • Perrin DD, Armarego WLF. Purification of Laboratory Chemicals. Pergamon: Oxford; 1989.
  • Young GJ, Onyebuagu W. Synthesis and characterization of di-disubstituted phthalocyanines. J. Org. Chem. 55 (1990) 2155-2159.
  • Yildirim N, Bekircan O. Use of ester formylhydrazones for the synthesis of 1,2,4-triazole and 1,3,4-oxadiazole derivatives. 37 (2013) 160-163.
  • Biyiklioglu Z, Bekircan O. Synthesis and electrochemical properties of axially disubstituted silicon phthalocyanine and peripherally tetra substituted manganese(III) 28. Ghanem BS, Piskin M, Durmus M, El-Khouly ME, Al-Raqa SY. phthalocyanine bearing 1,2,4-triazole substituents. Synthetic Metals. 200 (2014) 148-155.
  • Demirbaş Ü. Göl C, Barut B, Bayrak R, Durmuş M, Kantekin H, Değirmencioğlu İ. Peripherally and non-peripherally tetra-benzothiazole substituted metal-free zinc (II) and lead (II) phthalocyanines: Synthesis, characterization, and investigation of photophysical and photochemical properties. Journal of Molecular Structure. 1130 (2017) 677–687.
  • Bayrak R, Akçay HT, Bıyıklıoğlu Z, Değirmencioğlu İ. 30. Demirbaş Ü, Akyüz D, Barut B, Bayrak R, Koca A, Kantekin Substituted phthalocyanines and their electropolymerization properties. Synthetic Metals. 220 (2016) 643–652.
  • Nas A, Kantekin H, Durmuş M, Gümrükçüoğlu N. Unmetallated and metallated phthalocyanines bearing oxadiazole groups: Synthesis, photophysical and photochemical studies. 31. Demirbas Ü, Akçay HT, Koca A, Kantekin H. Synthesis, Journal of Luminescence. 154 (2014) 15–21.
  • Dilber G, Durmuş M, Kantekin H, Çakır V. Synthesis and characterization of a new soluble metal-free and metallophthalocyanines bearing biphenyl-4-yl methoxy groups. Journal of Organometallic Chemistry. 696 (2011) 2805–2814.
  • Demirbaş Ü, Pişkin M, Bayrak R, Ünlüer D, Dügdü E, Durmuş M, Kantekin H. The determination of photophysical and photochemical parameters of novel metal-free, zinc(II) and lead(II) phthalocyanines bearing 1,2,4- triazole groups. Synthetic Metals. 219 (2016) 76–82.
  • Demirbaş Ü, Pişkin M, Barut B, Bayrak R, Durmuş M, Kantekin H. Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3- (2H-benzo[d][1,2,3]triazol-2-yl)- 4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties. Synthetic Metals. 220 (2016) 276–285. Synthesis, photophysical and photochemical properties of novel phthalocyanines substituted with triptycene moieties. Polyhedron. 90 (2015) 85–90.
  • Demirbaş Ü, Akyüz D, Mermer A, Akçay HT, Demirbaş N, Koca A, Kantekin H. The electrochemical and spectroelectrochemical properties of metal free and metallophthalocyanines containing triazole/piperazine units. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 153 (2016) 478–487.

Triazole Substituted Phthalocyanines and Their Electrochemical Properties

Year 2018, Volume: 5 Issue: 1, 7 - 12, 28.03.2018
https://doi.org/10.17350/HJSE19030000071

Abstract

New cobalt II , zinc II , tin II and metal free phthaloyanines having peripherally triazole and Schiff’s base groups on were synthesized and their electrochemical properties were studied. In the first step of the synthetic procedure, triazole moiety, in the second step Shiff base moiety and in the third step key compound substituted phthalonitrile have been synthesized successfully in high yield. At the final stage target phthalocyanines have been obtained and characterized by combination of spectral analysis. The electrochemical measurements showed that while Free- and Sn-Pc give irreversible oxidation process, Co- and Zn- phthalocyanines give quasi-reversible electron transfer reaction in dichloromethane solution.

References

  • Akçay HT, Çoruh U, Bayrak R, Menteşe E, Vazquez Lopez EM. A spectroscopic study on new phthalonitrile derivative and its computational background: 4-[(4,5-Diphenyl- 4H-1,2,4-triazol-3-yl)sulfanyl]benzene-phthalonitrile. Journal of Molecular Structure. 1127 (2017) 539-548.
  • Khanmohammadi H, Abnosi MH, Hosseinzadeh A, Erfantalab M. Synthesis, biological and computational study of new Schiff base hydrazones bearing 3-(4-pyridine)-5- mercapto-1,2,4-triazole moiety. Spectrochim. Acta A 71 (2008) 1474-1480.
  • Li Z, Gu Z, Yin K, Zhang R, Deng Q, Xiang J. Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified D-glucopyranosyl residues and their antiproliferative activities. Eur. J. Med. Chem. 44 (2009) 4716-4720.
  • Bagihalli GB, Avaji PG, Patil SA, Badami PS. Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Eur. J. Med. Chem. 43 (2008) 2639-2649.
  • Ferrer S, Haasnoot JG, Reedijk J, Muller E, Cingi MB, Lanfranchi M, Manotti AM, Ribas LJ. Trinuclear N,N-bridged copper(II) complexes involving a Cu3OH core: [Cu-3(mu(3)- OH)L(3)A(H2O)(2)]A center dot(H2O)(x) {L=3-acetylamino- 1,2,4-triazolate; a = CF3SO3, NO3, ClO4; x = 0, 2} synthesis, X-ray structures, spectroscopy, and magnetic properties. Inorg. Chem. 39 (2000) 1859-1867.
  • Karaca H, Sezer S, Özalp-Yaman Ş, Tanyeli C. Concise synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines having triazole functionality, Polyhedron. 72 (2014) 147-156.
  • Nas A, Fandaklı S, Kantekin H, Demirbaş A, Durmuş M. Novel organosoluble metal-free and metallophthalocyanines bearing triazole moieties: Microwave assisted synthesis and determination of photophysical and photochemical properties. Dyes and Pigments. 95 (2012) 8-17.
  • Demirbaş Ü, Kobak RZU, Akçay HT, Ünlüer D, Koca A, Çelik F, Kantekin H. Synthesis, characterization, electrochemical and spectroelectrochemical properties of novel peripherally tetra-1,2,4-triazole substituted phthalocyanines. Synthetic Metals. 215 (2016) 68-76.
  • Perrin DD, Armarego WLF. Purification of Laboratory Chemicals. Pergamon: Oxford; 1989.
  • Young GJ, Onyebuagu W. Synthesis and characterization of di-disubstituted phthalocyanines. J. Org. Chem. 55 (1990) 2155-2159.
  • Yildirim N, Bekircan O. Use of ester formylhydrazones for the synthesis of 1,2,4-triazole and 1,3,4-oxadiazole derivatives. 37 (2013) 160-163.
  • Biyiklioglu Z, Bekircan O. Synthesis and electrochemical properties of axially disubstituted silicon phthalocyanine and peripherally tetra substituted manganese(III) 28. Ghanem BS, Piskin M, Durmus M, El-Khouly ME, Al-Raqa SY. phthalocyanine bearing 1,2,4-triazole substituents. Synthetic Metals. 200 (2014) 148-155.
  • Demirbaş Ü. Göl C, Barut B, Bayrak R, Durmuş M, Kantekin H, Değirmencioğlu İ. Peripherally and non-peripherally tetra-benzothiazole substituted metal-free zinc (II) and lead (II) phthalocyanines: Synthesis, characterization, and investigation of photophysical and photochemical properties. Journal of Molecular Structure. 1130 (2017) 677–687.
  • Bayrak R, Akçay HT, Bıyıklıoğlu Z, Değirmencioğlu İ. 30. Demirbaş Ü, Akyüz D, Barut B, Bayrak R, Koca A, Kantekin Substituted phthalocyanines and their electropolymerization properties. Synthetic Metals. 220 (2016) 643–652.
  • Nas A, Kantekin H, Durmuş M, Gümrükçüoğlu N. Unmetallated and metallated phthalocyanines bearing oxadiazole groups: Synthesis, photophysical and photochemical studies. 31. Demirbas Ü, Akçay HT, Koca A, Kantekin H. Synthesis, Journal of Luminescence. 154 (2014) 15–21.
  • Dilber G, Durmuş M, Kantekin H, Çakır V. Synthesis and characterization of a new soluble metal-free and metallophthalocyanines bearing biphenyl-4-yl methoxy groups. Journal of Organometallic Chemistry. 696 (2011) 2805–2814.
  • Demirbaş Ü, Pişkin M, Bayrak R, Ünlüer D, Dügdü E, Durmuş M, Kantekin H. The determination of photophysical and photochemical parameters of novel metal-free, zinc(II) and lead(II) phthalocyanines bearing 1,2,4- triazole groups. Synthetic Metals. 219 (2016) 76–82.
  • Demirbaş Ü, Pişkin M, Barut B, Bayrak R, Durmuş M, Kantekin H. Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3- (2H-benzo[d][1,2,3]triazol-2-yl)- 4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties. Synthetic Metals. 220 (2016) 276–285. Synthesis, photophysical and photochemical properties of novel phthalocyanines substituted with triptycene moieties. Polyhedron. 90 (2015) 85–90.
  • Demirbaş Ü, Akyüz D, Mermer A, Akçay HT, Demirbaş N, Koca A, Kantekin H. The electrochemical and spectroelectrochemical properties of metal free and metallophthalocyanines containing triazole/piperazine units. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 153 (2016) 478–487.
There are 19 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Rıza Bayrak This is me

Publication Date March 28, 2018
Published in Issue Year 2018 Volume: 5 Issue: 1

Cite

Vancouver Bayrak R. Triazole Substituted Phthalocyanines and Their Electrochemical Properties. Hittite J Sci Eng. 2018;5(1):7-12.

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