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Synthesis of Novel Chalcone Substituted Metallophthalocyanines: Electrochemistry, Spectroelectrochemistry and Catalytic Oxidation of 2-mercaptoethanol

Year 2018, Volume: 5 Issue: 2, 701 - 718, 01.01.2018
https://doi.org/10.18596/jotcsa.351559

Abstract

Novel
metallophthalocyanines (M = Zn, Co)
carrying
on the four of the
peripheral positions (E)-1-(furan-2-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one as
chalcone were sythesized.
These complexes
have been characterized by a combination of FT-IR, 1H-NMR, HRMS and
UV–Vis spectroscopy techniques. Also cyclic voltammograms of these
phthalocyanines were taken and obtained knowledge as zinc phthalocyanine have
one reduction reaction and cobalt phthalocyanine have two reduction reaction.
Spectroelectrochemical investigation shows the ring based reduction of MPc’s.
Pc-7 cobalt(II)phthalocyanine was investigated as catalyst in the catalytic
oxidation of 2-mercaptoethanol. Turnover number
,
initial reaction rate and the oxygen consumption was found in the catalytic
oxidation of 2-mercaptoethanol as 16.6, 
0.29, 2.52 recpectively.

References

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  • 2. Leznoff CC, editor. Phthalocyanines: properties and applications. Vol. 2. New York, NY: VCH; 1993.
  • 3. Leznoff C, Lever A, editors. Phthalocyanines: properties and applications. Vol. 3. Weinheim: Vch; 1993.
  • 4. Leznoff CC, Lever ABP, editors. Phthalocyanines: properties and applications. Volume 4. New York, NY: VCH; 1996.
  • 5. Xue J, Rand BP, Uchida S, Forrest SR. A hybrid planar–mixed molecular heterojunction photovoltaic cell. Advanced Materials. 2005;17(1):66–71.
  • 6. Shaheen SE, Ginley DS, Jabbour GE. Organic-based photovoltaics: toward low-cost power generation. MRS bulletin. 2005;30(1):10–19.
  • 7. Brumbach M, Placencia D, Armstrong NR. Titanyl phthalocyanine/C60 heterojunctions: Band-edge offsets and photovoltaic device performance. The Journal of Physical Chemistry C. 2008;112(8):3142–3151.
  • 8. Thompson BC, Fréchet JM. Polymer–fullerene composite solar cells. Angewandte chemie international edition. 2008;47(1):58–77.
  • 9. Szostak J, Jarosz G, Signerski R. Photovoltaic properties of cadmium selenide–titanyl phthalocyanine planar heterojunction devices. Chemical Physics. 2015;456:57–60.
  • 10. Zeyada H, El-Nahass M, El-Menyawy E, El-Sawah A. Electrical and photovoltaic characteristics of indium phthalocyanine chloride/p-Si solar cell. Synthetic Metals. 2015;207:46–53.
  • 11. Bonnett R. Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chemical Society Reviews. 1995;24(1):19–33.
  • 12. Bonnett R. Progress with heterocyclic photosensitizers for the photodynamic therapy (PDT) of tumours. Journal of heterocyclic chemistry. 2002;39(3):455–470.
  • 13. Chan W-S, Brasseur N, La Madeleine G, Quellet R, Van Lier J. Efficacy and mechanism of aluminium phthalocyanine and its sulphonated derivatives mediated photodynamic therapy on murine tumours. European Journal of Cancer. 1997;33(11):1855–1859.
  • 14. Karaca H, Sezer S, Tanyeli C. Synthesis of L-prolinol substituted novel optically active phthalocyanines. Dyes and Pigments. 2011;90(2):100–105.
  • 15. Kurt Ö, Koca A, Gül A, Koçak MB. Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups. Synthetic Metals. 2015;206:72–83.
  • 16. Karaca H, Sezer S, Özalp-Yaman Ş, Tanyeli C. Concise synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines having triazole functionality. Polyhedron. 2014;72:147–156.
  • 17. Kobak RZU, Arı MU, Tekin A, Gül A. Aggregation behavior in unsymmetrically substituted metal-free phthalocyanines. Chemical Physics. 2015;448:91–97.
  • 18. Nas A, Kahriman N, Kantekin H, Yaylı N, Durmuş M. The synthesis of novel unmetallated and metallated phthalocyanines including (E)-4-(3-cinnamoylphenoxy) groups at the peripheral positions and photophysicochemical properties of their zinc phthalocyanine derivatives. Dyes and Pigments. 2013;99(1):90–98.
  • 19. Rusanova J, Pilkington M, Decurtins S. A novel fully conjugated phenanthroline-appended phthalocyanine: synthesis and characterisation. Chemical communications. 2002;(19):2236–2237.
  • 20. Li F, Liu Q, Liang Z, Wang J, Pang M, Huang W, vd. Synthesis and biological evaluation of peptide-conjugated phthalocyanine photosensitizers with highly hydrophilic modifications. Organic & biomolecular chemistry. 2016;14(13):3409–3422.
  • 21. Acar İ, Arslan T, Topçu S, Aktaş A, Şen S, Serencam H. Synthesis and electrochemistry of metallophthalocyanines bearing ${$4-[(2E)-3-(3, 4, 5-trimethoxyphenyl) prop-2-enoyl] phenoxy$}$ groups. Journal of Organometallic Chemistry. 2014;752:25–29.
  • 22. Yildiz SZ, Colak S, Tuna M. Non-ionic peripherally substituted soluble phthalocyanines: Synthesis characterization and investigation of their solution properties. Journal of Molecular Liquids. 2014;195:22–29.
  • 23. Ovchenkova EN, Bichan NG, Lomova TN. New soluble octakis-substituted Co (II) phthalocyanines: Synthesis, spectra, supramolecular chemistry. Dyes and Pigments. 2016;128:263–270.
  • 24. Ngo D, Kalala M, Hogan V, Manchanayakage R. One-pot synthesis of chalcone epoxides—A green chemistry strategy. Tetrahedron Letters. 2014;55(32):4496–4500.
  • 25. Ghouili A, Dusek M, Petricek V, Ayed TB, Hassen RB. Synthesis, crystal structure and spectral characteristics of highly fluorescent chalcone-based coumarin in solution and in polymer matrix. Journal of Physics and Chemistry of Solids. 2014;75(2):188–193.
  • 26. Niu C-G, Guan A-L, Zeng G-M, Liu Y-G, Li Z-W. Fluorescence water sensor based on covalent immobilization of chalcone derivative. Analytica chimica acta. 2006;577(2):264–270.
  • 27. Shan Y, Liu Z, Cao D, Sun Y, Wang K, Chen H. Nitro substituted chalcone derivatives as quick-response chemosensors for cyanide anions. Sensors and Actuators B: Chemical. 2014;198:15–19.
  • 28. Wei Y, Qin G, Wang W, Bian W, Shuang S, Dong C. Development of fluorescent FeIII sensor based on chalcone. Journal of Luminescence. 2011;131(8):1672–1676.
  • 29. Sun Y, Chen H, Cao D, Liu Z, Chen H, Deng Y, vd. Chalcone derivatives as fluorescence turn-on chemosensors for cyanide anions. Journal of Photochemistry and Photobiology A: Chemistry. 2012;244:65–70.
  • 30. Delavaux-Nicot B, Maynadié J, Lavabre D, Fery-Forgues S. Ca 2+ vs. Ba 2+ electrochemical detection by two disubstituted ferrocenyl chalcone chemosensors. Study of the ligand–metal interactions in CH 3 CN. Journal of organometallic chemistry. 2007;692(4):874–886.
  • 31. Gladkov L, Shkirman S, Sushko N, Konstantinova V, Sokolov N, Solovyov K. IR spectra of Zn phthalocyanine and Zn phthalocyanine-d 16 and their interpretation on the basis of normal coordinate analysis. Spectroscopy letters. 2001;34(6):709–719.
  • 32. Shinohara H, Tsaryova O, Schnurpfeil G, Wöhrle D. Differently substituted phthalocyanines: Comparison of calculated energy levels, singlet oxygen quantum yields, photo-oxidative stabilities, photocatalytic and catalytic activities. Journal of Photochemistry and Photobiology A: Chemistry. 2006;184(1):50–57.
  • 33. Pan Y, Chen W, Lu S, Zhang Y. Novel aqueous soluble cobalt phthalocyanine: synthesis and catalytic activity on oxidation of 2-mercaptoethanol. Dyes and pigments. 2005;66(2):115–121.
  • 34. Iliev VI, Ileva AI, Dimitrov LD. Catalytic oxidation of 2-mercaptoethanol by cobalt (II)-phthalocyanine complexes intercalated in layered double hydroxides. Applied Catalysis A: General. 1995;126(2):333–340.
  • 35. Karaca H, Çayeğil B, Sezer S. Synthesis characterization and metal sensing applications of novel chalcone substituted phthalocyanines. Synthetic Metals. 2016;215:134–141.
  • 36. Nombona N, Nyokong T. The synthesis, cyclic voltammetry and spectroelectrochemical studies of Co (II) phthalocyanines tetra-substituted at the α and β positions with phenylthio groups. Dyes and Pigments. 2009;80(1):130–135.
  • 37. Karaca H, Teker M, Gül A. Catalytic Oxidation of 2-Mercaptoethanol by a Water-Soluble Porhphyrazinatocobalt (II) Complex. Chem J. 2016;6(01):55–58.
  • 38. Karaca H, Akcay N, Teker M. PORPHYRAZINE IMMOBILIZATION ON POLYESTER FABRIC AND HETEROGENEOUS CATALYTIC APPLICATION ON OXIDATION OF 2-MERCAPTOETHANOL. FRESENIUS ENVIRONMENTAL BULLETIN. 2016;25(5):1714–1718.
  • 39. Karaca H, Tetrapirol Türevlerinin Katalitik Etkilerinin İncelemesi, PhD Thesis, Sakarya University, Institute Of Natural Sciences, 2004.
  • 40. Karaca H. Redox chemistry, spectroelectrochemistry and catalytic activity of novel synthesized phthalocyanines bearing four schiff bases on the periphery. Journal of Organometallic Chemistry. 2016;822:39–45.
Year 2018, Volume: 5 Issue: 2, 701 - 718, 01.01.2018
https://doi.org/10.18596/jotcsa.351559

Abstract

References

  • 1. Leznoff C, Lever A, editors. Phthalocyanines: Properties and applications. Vol. 1. New York: VCH; 1989.
  • 2. Leznoff CC, editor. Phthalocyanines: properties and applications. Vol. 2. New York, NY: VCH; 1993.
  • 3. Leznoff C, Lever A, editors. Phthalocyanines: properties and applications. Vol. 3. Weinheim: Vch; 1993.
  • 4. Leznoff CC, Lever ABP, editors. Phthalocyanines: properties and applications. Volume 4. New York, NY: VCH; 1996.
  • 5. Xue J, Rand BP, Uchida S, Forrest SR. A hybrid planar–mixed molecular heterojunction photovoltaic cell. Advanced Materials. 2005;17(1):66–71.
  • 6. Shaheen SE, Ginley DS, Jabbour GE. Organic-based photovoltaics: toward low-cost power generation. MRS bulletin. 2005;30(1):10–19.
  • 7. Brumbach M, Placencia D, Armstrong NR. Titanyl phthalocyanine/C60 heterojunctions: Band-edge offsets and photovoltaic device performance. The Journal of Physical Chemistry C. 2008;112(8):3142–3151.
  • 8. Thompson BC, Fréchet JM. Polymer–fullerene composite solar cells. Angewandte chemie international edition. 2008;47(1):58–77.
  • 9. Szostak J, Jarosz G, Signerski R. Photovoltaic properties of cadmium selenide–titanyl phthalocyanine planar heterojunction devices. Chemical Physics. 2015;456:57–60.
  • 10. Zeyada H, El-Nahass M, El-Menyawy E, El-Sawah A. Electrical and photovoltaic characteristics of indium phthalocyanine chloride/p-Si solar cell. Synthetic Metals. 2015;207:46–53.
  • 11. Bonnett R. Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chemical Society Reviews. 1995;24(1):19–33.
  • 12. Bonnett R. Progress with heterocyclic photosensitizers for the photodynamic therapy (PDT) of tumours. Journal of heterocyclic chemistry. 2002;39(3):455–470.
  • 13. Chan W-S, Brasseur N, La Madeleine G, Quellet R, Van Lier J. Efficacy and mechanism of aluminium phthalocyanine and its sulphonated derivatives mediated photodynamic therapy on murine tumours. European Journal of Cancer. 1997;33(11):1855–1859.
  • 14. Karaca H, Sezer S, Tanyeli C. Synthesis of L-prolinol substituted novel optically active phthalocyanines. Dyes and Pigments. 2011;90(2):100–105.
  • 15. Kurt Ö, Koca A, Gül A, Koçak MB. Synthesis, electrochemistry and in situ spectroelectrochemistry of novel hexadeca-substituted phthalocyanines with three different groups. Synthetic Metals. 2015;206:72–83.
  • 16. Karaca H, Sezer S, Özalp-Yaman Ş, Tanyeli C. Concise synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines having triazole functionality. Polyhedron. 2014;72:147–156.
  • 17. Kobak RZU, Arı MU, Tekin A, Gül A. Aggregation behavior in unsymmetrically substituted metal-free phthalocyanines. Chemical Physics. 2015;448:91–97.
  • 18. Nas A, Kahriman N, Kantekin H, Yaylı N, Durmuş M. The synthesis of novel unmetallated and metallated phthalocyanines including (E)-4-(3-cinnamoylphenoxy) groups at the peripheral positions and photophysicochemical properties of their zinc phthalocyanine derivatives. Dyes and Pigments. 2013;99(1):90–98.
  • 19. Rusanova J, Pilkington M, Decurtins S. A novel fully conjugated phenanthroline-appended phthalocyanine: synthesis and characterisation. Chemical communications. 2002;(19):2236–2237.
  • 20. Li F, Liu Q, Liang Z, Wang J, Pang M, Huang W, vd. Synthesis and biological evaluation of peptide-conjugated phthalocyanine photosensitizers with highly hydrophilic modifications. Organic & biomolecular chemistry. 2016;14(13):3409–3422.
  • 21. Acar İ, Arslan T, Topçu S, Aktaş A, Şen S, Serencam H. Synthesis and electrochemistry of metallophthalocyanines bearing ${$4-[(2E)-3-(3, 4, 5-trimethoxyphenyl) prop-2-enoyl] phenoxy$}$ groups. Journal of Organometallic Chemistry. 2014;752:25–29.
  • 22. Yildiz SZ, Colak S, Tuna M. Non-ionic peripherally substituted soluble phthalocyanines: Synthesis characterization and investigation of their solution properties. Journal of Molecular Liquids. 2014;195:22–29.
  • 23. Ovchenkova EN, Bichan NG, Lomova TN. New soluble octakis-substituted Co (II) phthalocyanines: Synthesis, spectra, supramolecular chemistry. Dyes and Pigments. 2016;128:263–270.
  • 24. Ngo D, Kalala M, Hogan V, Manchanayakage R. One-pot synthesis of chalcone epoxides—A green chemistry strategy. Tetrahedron Letters. 2014;55(32):4496–4500.
  • 25. Ghouili A, Dusek M, Petricek V, Ayed TB, Hassen RB. Synthesis, crystal structure and spectral characteristics of highly fluorescent chalcone-based coumarin in solution and in polymer matrix. Journal of Physics and Chemistry of Solids. 2014;75(2):188–193.
  • 26. Niu C-G, Guan A-L, Zeng G-M, Liu Y-G, Li Z-W. Fluorescence water sensor based on covalent immobilization of chalcone derivative. Analytica chimica acta. 2006;577(2):264–270.
  • 27. Shan Y, Liu Z, Cao D, Sun Y, Wang K, Chen H. Nitro substituted chalcone derivatives as quick-response chemosensors for cyanide anions. Sensors and Actuators B: Chemical. 2014;198:15–19.
  • 28. Wei Y, Qin G, Wang W, Bian W, Shuang S, Dong C. Development of fluorescent FeIII sensor based on chalcone. Journal of Luminescence. 2011;131(8):1672–1676.
  • 29. Sun Y, Chen H, Cao D, Liu Z, Chen H, Deng Y, vd. Chalcone derivatives as fluorescence turn-on chemosensors for cyanide anions. Journal of Photochemistry and Photobiology A: Chemistry. 2012;244:65–70.
  • 30. Delavaux-Nicot B, Maynadié J, Lavabre D, Fery-Forgues S. Ca 2+ vs. Ba 2+ electrochemical detection by two disubstituted ferrocenyl chalcone chemosensors. Study of the ligand–metal interactions in CH 3 CN. Journal of organometallic chemistry. 2007;692(4):874–886.
  • 31. Gladkov L, Shkirman S, Sushko N, Konstantinova V, Sokolov N, Solovyov K. IR spectra of Zn phthalocyanine and Zn phthalocyanine-d 16 and their interpretation on the basis of normal coordinate analysis. Spectroscopy letters. 2001;34(6):709–719.
  • 32. Shinohara H, Tsaryova O, Schnurpfeil G, Wöhrle D. Differently substituted phthalocyanines: Comparison of calculated energy levels, singlet oxygen quantum yields, photo-oxidative stabilities, photocatalytic and catalytic activities. Journal of Photochemistry and Photobiology A: Chemistry. 2006;184(1):50–57.
  • 33. Pan Y, Chen W, Lu S, Zhang Y. Novel aqueous soluble cobalt phthalocyanine: synthesis and catalytic activity on oxidation of 2-mercaptoethanol. Dyes and pigments. 2005;66(2):115–121.
  • 34. Iliev VI, Ileva AI, Dimitrov LD. Catalytic oxidation of 2-mercaptoethanol by cobalt (II)-phthalocyanine complexes intercalated in layered double hydroxides. Applied Catalysis A: General. 1995;126(2):333–340.
  • 35. Karaca H, Çayeğil B, Sezer S. Synthesis characterization and metal sensing applications of novel chalcone substituted phthalocyanines. Synthetic Metals. 2016;215:134–141.
  • 36. Nombona N, Nyokong T. The synthesis, cyclic voltammetry and spectroelectrochemical studies of Co (II) phthalocyanines tetra-substituted at the α and β positions with phenylthio groups. Dyes and Pigments. 2009;80(1):130–135.
  • 37. Karaca H, Teker M, Gül A. Catalytic Oxidation of 2-Mercaptoethanol by a Water-Soluble Porhphyrazinatocobalt (II) Complex. Chem J. 2016;6(01):55–58.
  • 38. Karaca H, Akcay N, Teker M. PORPHYRAZINE IMMOBILIZATION ON POLYESTER FABRIC AND HETEROGENEOUS CATALYTIC APPLICATION ON OXIDATION OF 2-MERCAPTOETHANOL. FRESENIUS ENVIRONMENTAL BULLETIN. 2016;25(5):1714–1718.
  • 39. Karaca H, Tetrapirol Türevlerinin Katalitik Etkilerinin İncelemesi, PhD Thesis, Sakarya University, Institute Of Natural Sciences, 2004.
  • 40. Karaca H. Redox chemistry, spectroelectrochemistry and catalytic activity of novel synthesized phthalocyanines bearing four schiff bases on the periphery. Journal of Organometallic Chemistry. 2016;822:39–45.
There are 40 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Hüseyin Karaca

Publication Date January 1, 2018
Submission Date November 13, 2017
Acceptance Date April 16, 2018
Published in Issue Year 2018 Volume: 5 Issue: 2

Cite

Vancouver Karaca H. Synthesis of Novel Chalcone Substituted Metallophthalocyanines: Electrochemistry, Spectroelectrochemistry and Catalytic Oxidation of 2-mercaptoethanol. JOTCSA. 2018;5(2):701-18.

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