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Suda Çözünür Yeni Ftalosiyaninlerin Sentezi ve Fotofizikokimyasal Özelliklerinin İncelenmesi

Year 2017, Volume: 17 Issue: 2, 469 - 478, 31.08.2017

Abstract

Bu çalışmada periferal olmayan konumlarında tetra sübstitüe karboksilik asit uçları içeren,
suda çözünür, dört yeni ftalosiyanin türevi sentezlenmiştir. Bunun için öncelikle 3-
nitroftalonitril ile 4-merkaptobenzoikasit tepkimeye sokularak yeni bir ftalonitril türevi (1) elde
edilmiştir. Bu yeni ftalonitril türevi FTIR, 1H NMR ve MS gibi spektroskopik teknikler ile
elementel analiz kullanılarak karakterize edilmiştir. 1 bileşiğinden çıkılarak metalsiz (2a), çinko
(2b), kobalt (2c) ve nikel (2d) metalli dört farklı ve suda çözünür ftalosiyanin türevi
sentezlenmiştir. Bu türevler arasındaki metalsiz ve çinko ftalosiyaninlerin fotofiziksel ve
fotokimyasal özellikleri incelenmiştir. Fotofiziksel özellik olarak bileşiklerin (2a ve 2b) floresans
emisyon ve uyarılma spektrumları alınmış, floresans kuantum verimleri ile floresans ömürleri
hesaplanmıştır. Fotokimyasal çalışma olarak ise bileşiklerin (2a ve 2b) singlet oksijen kuantum
verimleri hesaplanmıştır. Elde edilen sonuçlar ışığında özellikle 2b bileşiği, atık sulardaki
organik kirleticilerin foto bozunmasında kullanılmak üzere önerilebilir.

References

  • Allen, C.M., Sharman, W.M. and Van Lier, J.E., 2001. Current status of phthalocyanines in the photodynamic therapy of cancer.J. Porphyr. Phthalocyanines,5, 161–169.
  • Atmaca, G.Y., Dizman, C., Eren, T. and Erdoğmuş, A., 2015.Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties.Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 137, 244–249.
  • Braun, A. and Tcherniac, J., 1907. Berichte der deutschen chemischen Gesellschaft.Ber.Deutsch. Chem. Ges.,40, 2709-2714.
  • De Diesbach, H. and Von der Weid, E., 1927. Quelques Sels Complexes o-Dinitriles avec le Cuivre la Pyridine.Helv.Chim.Acta.,10, 886-887.
  • Dinçer, H., Mert, H., Çalış, E., Yaşa, G. and Erdogmuş, A., 2015. Synthesis and photophysicochemical studies of poly(ethylene glycol) conjugated symmetrical and asymmetrical zinc phthalocyanines. Journal of Molecular Structure, 1102, 190-196.
  • Du, H., Fuh, R.A., Li, J., Corkan, A. and Lindsey J.S., 1998. PhotochemCAD†: A Computer-Aided Design and Research Tool in Photochemistry. Photochem.Photobiol.,68, 141-142.
  • Durmuş, M. and Nyokong, T., 2008. Photophysicochemical and Fluorescence Quenching Studies of Benzyloxyphenoxy Substituted Zinc Phthalocyanines. Spectrochim. Acta A,69, 1170–1177.
  • Durmuş¸ M. and Nyokong, T., 2007.Synthesis and solvent effects on the aggregation and fluorescence properties of substituted zinc phthalocyanines.Polyhedron, 26, 2767–2776.
  • Giuntini, F., Raoul Y., Dei, D., et al., 2005. Synthesis of tetrasubstituted Zn(II)-phthalocyanines carrying four carboranyl-units as potential BNCT and PDT agents. Tetrahedron Let.,46, 2979–2982.
  • Gouterman, M., 1961.Spectra of porphyrins.J. Mol. Spec., 6, 138-163. Kadish, K., Smith, K. and Guilard, R., 2003. The Porphyrin Handbook. Tokyo, Academic Press.
  • Khoza, P., Nyokong , T., 2015. Photocatalytic behaviour of zinc tetraamino phthalocyanine-silver nanoparticles immobilized on chitosan beads.Journal of Molecular Catalysis A: Chemical,399, 25–32.
  • Kırbaç, E. Atmaca, G. Y. and Erdoğmuş, A., 2014. Novel highly soluble fluoro, chloro, bromo-phenoxy-phenoxy substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties.J. Organomet. Chem.,752, 115–122. Köksoy, B., Durmuş, M. and Bulut, M., 2015.
  • Tetra- and octa-[4-(2-hydroxyethyl)phenoxy bearing novel metal-free and zinc(II) phthalocyanines: Synthesis, characterization and investigation of photophysicochemical properties. Journal of Luminescence,161, 95–102.
  • Linstead, R.P., 1934. Phthalocyanines I.A New Type of Synthetic Coloring Matters.J. Chem. Soc.,28, 1016-1017.
  • Mack, J. and Stillman, M.J., 2001. Assignment of the optical spectra of metal phthalocyanines through spectral band deconvolution analysis and ZİNDO calculations. Coordin. Chem. Rev.,219, 993-1032.
  • Marais, E., Klein, R., Antunes, E. and Nyokong, T., 2007.Photocatalysis of 4-nitrophenol using zinc phthalocyanine complexes.J. Mol. Catal. A: Chem.,261, 36–42.
  • Maree, S.E. and Nyokong, T., 2001. Syntheses and photochemical properties of octasubstituted phthalocyaninato zinc complexes. J. Porphyrin. Phthalocyanines.,5, 782-792.
  • McKeown, N.B., 1998. Phthalocyanine Materials—Synthesis, Structure and Function. Cambridge, Cambridge University Press. Miller, J.D., Baron, E.D., Scull, H., Hsia, A., Berlin, J.C., McCormick, T., Colussi, V., Kenney, M.E., Copper, K.D. and Oleinick, N.L., 2007. Photodynamic therapy with the phthalocyanine photosensitizer Pc 4: the case experience with preclinical mechanistic and early clinical–translational studies. Toxicol. Appl. Pharmacol.,224, 290–299.
  • Musluoğlu, E., Gürek, A., Ahsen, V., Gül, A., Bekaroğlu, Ö., 1992. Unsymmetrical Phthalocyanines with a Single Macrocyclic Substituent.Chem. Ber.,125, 2337-2339.
  • Nombona, N., Chidawanyika, W. and Nyokong, T., 2012.Spectroscopic and physicochemical behavior of magnesium phthalocyanine derivatives mono-substituted with a carboxylic acid group.J. Molec. Structure,1012, 31–36.
  • Ogunbayo, T.B. and Nyokong, T., 2010. Photophysical and photochemical properties of Ni(II), Pd(II) and Pt(II) aryloxo and alkylthio derivatised phthalocyanine. J. Mol. truct.,973, 96–103. Ogunsipe, A., Chen, J.Y., Nyokong, T., 2004. Photophysical and photochemical studies of zinc(II) phthalocyanine derivatives—effects of substituents and solvents. New J. Chem.,7, 822-827.
  • Ogunsipe, A., Maree, D., Nyokong, T., 2003.Solvent effects on the photochemical and fluorescence properties of zinc phthalocyanine derivatives.J. Mol. Struct., 650, 131–140.
  • Oluwole, D.O., Prinsloo, E. and Nyokong, T., 2017.Photophysical behavior and photodynamic therapy activity of conjugates of zinc monocarboxyphenoxy phthalocyanine with human serum albumin and chitosan.Spectrochimica Acta Part A: Molecular and Biomolecular Spect.,173, 292–300.
  • Robertson, J. M., 1935. An X-Ray Study of the Structure of the Phthalocyanines. I. Metal-Free, Nickel, Copper and Platinum Compounds.Journal of the Chemical Soc.,29, 615-621.
  • Strickler, S. J. and Berg, R.A., 1962.Relationship between Absorption Intensity and Fluorescence Lifetime of Molecules.J. Chem. Phys.,37, 814-822.
  • Turek, P., Petit, P., Andre, J.J., Simon, J., Even, R., Boudjema, B., Guillaud, G. and Maitrot, M., 1987. A New Series of Molecular Semiconductors: Phthalocyanine Radicals. J. Am. Chem. Soc.,109, 5119-5122.
  • Wöhrle, D., Suvorova, O., Gerdes, R., Bartels, O., Lapok, L., Baziakina, N., Makarov, S. and Slodek, A., 2004.Efficient Oxidations and Photooxidations with Molecular Oxygen using Metal Phthalocyanines as Catalysts and Photocatalysts.J. Porphyrins Phthalocyanines,8,1020–1041.
  • a.Yılmaz, Y., Erdoğmuş A. and Şener, M.K., 2014. Diphenylethoxy-substituted metal-free and metallophthalocyanines as potential photosensitizer for photodynamic therapy: synthesis and photophysical and photochemical properties. Turk J Chem., 38, 1083- 1093.
  • b.Yılmaz, Y., Mack, J., Şener, M. K., Sönmez, M. and Nyokong, T. 2014.Photophysical and Photochemical Properties and TD-DFT Calculations of Novel Highly Soluble Zinc and Platinum Phthalocyanines.Journal of Photochemistry and Photobiology A:Chemistry,277, 102–110.
Year 2017, Volume: 17 Issue: 2, 469 - 478, 31.08.2017

Abstract

References

  • Allen, C.M., Sharman, W.M. and Van Lier, J.E., 2001. Current status of phthalocyanines in the photodynamic therapy of cancer.J. Porphyr. Phthalocyanines,5, 161–169.
  • Atmaca, G.Y., Dizman, C., Eren, T. and Erdoğmuş, A., 2015.Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties.Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 137, 244–249.
  • Braun, A. and Tcherniac, J., 1907. Berichte der deutschen chemischen Gesellschaft.Ber.Deutsch. Chem. Ges.,40, 2709-2714.
  • De Diesbach, H. and Von der Weid, E., 1927. Quelques Sels Complexes o-Dinitriles avec le Cuivre la Pyridine.Helv.Chim.Acta.,10, 886-887.
  • Dinçer, H., Mert, H., Çalış, E., Yaşa, G. and Erdogmuş, A., 2015. Synthesis and photophysicochemical studies of poly(ethylene glycol) conjugated symmetrical and asymmetrical zinc phthalocyanines. Journal of Molecular Structure, 1102, 190-196.
  • Du, H., Fuh, R.A., Li, J., Corkan, A. and Lindsey J.S., 1998. PhotochemCAD†: A Computer-Aided Design and Research Tool in Photochemistry. Photochem.Photobiol.,68, 141-142.
  • Durmuş, M. and Nyokong, T., 2008. Photophysicochemical and Fluorescence Quenching Studies of Benzyloxyphenoxy Substituted Zinc Phthalocyanines. Spectrochim. Acta A,69, 1170–1177.
  • Durmuş¸ M. and Nyokong, T., 2007.Synthesis and solvent effects on the aggregation and fluorescence properties of substituted zinc phthalocyanines.Polyhedron, 26, 2767–2776.
  • Giuntini, F., Raoul Y., Dei, D., et al., 2005. Synthesis of tetrasubstituted Zn(II)-phthalocyanines carrying four carboranyl-units as potential BNCT and PDT agents. Tetrahedron Let.,46, 2979–2982.
  • Gouterman, M., 1961.Spectra of porphyrins.J. Mol. Spec., 6, 138-163. Kadish, K., Smith, K. and Guilard, R., 2003. The Porphyrin Handbook. Tokyo, Academic Press.
  • Khoza, P., Nyokong , T., 2015. Photocatalytic behaviour of zinc tetraamino phthalocyanine-silver nanoparticles immobilized on chitosan beads.Journal of Molecular Catalysis A: Chemical,399, 25–32.
  • Kırbaç, E. Atmaca, G. Y. and Erdoğmuş, A., 2014. Novel highly soluble fluoro, chloro, bromo-phenoxy-phenoxy substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties.J. Organomet. Chem.,752, 115–122. Köksoy, B., Durmuş, M. and Bulut, M., 2015.
  • Tetra- and octa-[4-(2-hydroxyethyl)phenoxy bearing novel metal-free and zinc(II) phthalocyanines: Synthesis, characterization and investigation of photophysicochemical properties. Journal of Luminescence,161, 95–102.
  • Linstead, R.P., 1934. Phthalocyanines I.A New Type of Synthetic Coloring Matters.J. Chem. Soc.,28, 1016-1017.
  • Mack, J. and Stillman, M.J., 2001. Assignment of the optical spectra of metal phthalocyanines through spectral band deconvolution analysis and ZİNDO calculations. Coordin. Chem. Rev.,219, 993-1032.
  • Marais, E., Klein, R., Antunes, E. and Nyokong, T., 2007.Photocatalysis of 4-nitrophenol using zinc phthalocyanine complexes.J. Mol. Catal. A: Chem.,261, 36–42.
  • Maree, S.E. and Nyokong, T., 2001. Syntheses and photochemical properties of octasubstituted phthalocyaninato zinc complexes. J. Porphyrin. Phthalocyanines.,5, 782-792.
  • McKeown, N.B., 1998. Phthalocyanine Materials—Synthesis, Structure and Function. Cambridge, Cambridge University Press. Miller, J.D., Baron, E.D., Scull, H., Hsia, A., Berlin, J.C., McCormick, T., Colussi, V., Kenney, M.E., Copper, K.D. and Oleinick, N.L., 2007. Photodynamic therapy with the phthalocyanine photosensitizer Pc 4: the case experience with preclinical mechanistic and early clinical–translational studies. Toxicol. Appl. Pharmacol.,224, 290–299.
  • Musluoğlu, E., Gürek, A., Ahsen, V., Gül, A., Bekaroğlu, Ö., 1992. Unsymmetrical Phthalocyanines with a Single Macrocyclic Substituent.Chem. Ber.,125, 2337-2339.
  • Nombona, N., Chidawanyika, W. and Nyokong, T., 2012.Spectroscopic and physicochemical behavior of magnesium phthalocyanine derivatives mono-substituted with a carboxylic acid group.J. Molec. Structure,1012, 31–36.
  • Ogunbayo, T.B. and Nyokong, T., 2010. Photophysical and photochemical properties of Ni(II), Pd(II) and Pt(II) aryloxo and alkylthio derivatised phthalocyanine. J. Mol. truct.,973, 96–103. Ogunsipe, A., Chen, J.Y., Nyokong, T., 2004. Photophysical and photochemical studies of zinc(II) phthalocyanine derivatives—effects of substituents and solvents. New J. Chem.,7, 822-827.
  • Ogunsipe, A., Maree, D., Nyokong, T., 2003.Solvent effects on the photochemical and fluorescence properties of zinc phthalocyanine derivatives.J. Mol. Struct., 650, 131–140.
  • Oluwole, D.O., Prinsloo, E. and Nyokong, T., 2017.Photophysical behavior and photodynamic therapy activity of conjugates of zinc monocarboxyphenoxy phthalocyanine with human serum albumin and chitosan.Spectrochimica Acta Part A: Molecular and Biomolecular Spect.,173, 292–300.
  • Robertson, J. M., 1935. An X-Ray Study of the Structure of the Phthalocyanines. I. Metal-Free, Nickel, Copper and Platinum Compounds.Journal of the Chemical Soc.,29, 615-621.
  • Strickler, S. J. and Berg, R.A., 1962.Relationship between Absorption Intensity and Fluorescence Lifetime of Molecules.J. Chem. Phys.,37, 814-822.
  • Turek, P., Petit, P., Andre, J.J., Simon, J., Even, R., Boudjema, B., Guillaud, G. and Maitrot, M., 1987. A New Series of Molecular Semiconductors: Phthalocyanine Radicals. J. Am. Chem. Soc.,109, 5119-5122.
  • Wöhrle, D., Suvorova, O., Gerdes, R., Bartels, O., Lapok, L., Baziakina, N., Makarov, S. and Slodek, A., 2004.Efficient Oxidations and Photooxidations with Molecular Oxygen using Metal Phthalocyanines as Catalysts and Photocatalysts.J. Porphyrins Phthalocyanines,8,1020–1041.
  • a.Yılmaz, Y., Erdoğmuş A. and Şener, M.K., 2014. Diphenylethoxy-substituted metal-free and metallophthalocyanines as potential photosensitizer for photodynamic therapy: synthesis and photophysical and photochemical properties. Turk J Chem., 38, 1083- 1093.
  • b.Yılmaz, Y., Mack, J., Şener, M. K., Sönmez, M. and Nyokong, T. 2014.Photophysical and Photochemical Properties and TD-DFT Calculations of Novel Highly Soluble Zinc and Platinum Phthalocyanines.Journal of Photochemistry and Photobiology A:Chemistry,277, 102–110.
There are 29 citations in total.

Details

Primary Language Turkish
Journal Section Articles
Authors

Yusuf Yılmaz

Anwar Youssef This is me

Mehmet Sönmez This is me

Publication Date August 31, 2017
Submission Date January 24, 2017
Published in Issue Year 2017 Volume: 17 Issue: 2

Cite

APA Yılmaz, Y., Youssef, A., & Sönmez, M. (2017). Suda Çözünür Yeni Ftalosiyaninlerin Sentezi ve Fotofizikokimyasal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 17(2), 469-478.
AMA Yılmaz Y, Youssef A, Sönmez M. Suda Çözünür Yeni Ftalosiyaninlerin Sentezi ve Fotofizikokimyasal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. August 2017;17(2):469-478.
Chicago Yılmaz, Yusuf, Anwar Youssef, and Mehmet Sönmez. “Suda Çözünür Yeni Ftalosiyaninlerin Sentezi Ve Fotofizikokimyasal Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 17, no. 2 (August 2017): 469-78.
EndNote Yılmaz Y, Youssef A, Sönmez M (August 1, 2017) Suda Çözünür Yeni Ftalosiyaninlerin Sentezi ve Fotofizikokimyasal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 17 2 469–478.
IEEE Y. Yılmaz, A. Youssef, and M. Sönmez, “Suda Çözünür Yeni Ftalosiyaninlerin Sentezi ve Fotofizikokimyasal Özelliklerinin İncelenmesi”, Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 17, no. 2, pp. 469–478, 2017.
ISNAD Yılmaz, Yusuf et al. “Suda Çözünür Yeni Ftalosiyaninlerin Sentezi Ve Fotofizikokimyasal Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 17/2 (August 2017), 469-478.
JAMA Yılmaz Y, Youssef A, Sönmez M. Suda Çözünür Yeni Ftalosiyaninlerin Sentezi ve Fotofizikokimyasal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2017;17:469–478.
MLA Yılmaz, Yusuf et al. “Suda Çözünür Yeni Ftalosiyaninlerin Sentezi Ve Fotofizikokimyasal Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 17, no. 2, 2017, pp. 469-78.
Vancouver Yılmaz Y, Youssef A, Sönmez M. Suda Çözünür Yeni Ftalosiyaninlerin Sentezi ve Fotofizikokimyasal Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2017;17(2):469-78.