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Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine

Year 2021, Volume: 9 Issue: Special 1, 58 - 64, 30.04.2021
https://doi.org/10.51354/mjen.884756

Abstract

 2(3),9(10),16(17),23(24)-tetrakis-2,6-dimethoxyphenoxy substituted magnesium (II) phthalocyanine, which has very good solubility in polar and non-polar solvents and does not aggregate, was synthesized. Its structure was characterized by spectroscopic methods such as elemental analysis, UV-vis, FT-IR, MALDI-TOF mass and 1H NMR. It has very good solubility in polar aprotic solvents such as dimethyl sulfoxide, N, N- Dimethylformamide, tetrahydrofuran, dichloromethane, and non-polar solvents such as toluene, chloroform. Its aggregation properties have been studied both in the solvents mentioned above and in N, N- Dimethylformamide at different concentrations. Its photophysical properties were determined in N, N-dimethyl formamide. The effects of the nature and presence of 2,6-dimethoxyphenoxy group, which is an antioxidant derivative, on the phthalocyanine skeleton on the spectroscopic and photophysical properties were investigated by comparing it with unsubstituted magnesium (II) phthalocyanine. It can be a good nominee for various technological applications in that it does not aggregate and has good solubility in polar and non-polar solvents, as well as better and favorable fluorescence properties than its analog in the previous study.

Supporting Institution

Çanakkale Onsekiz Mart University, The Scientific Research Coordination Unit

Project Number

FBA-2021-3355

References

  • Referans1 Ingram D.J.E., Bennett J.E., “Paramagnetic resonance in phthalocyanine, chlorophyll, and hemoglobin derivatives”, The Journal of Chemical Physics, 22(6), (1954), 1136-1137.
  • Referans2 Tian M., Wada T., Kimura-Sudab H., Sasabea H., “Novel non-aggregated unsymmetrical metallophthalocyanines for second-order non-linear optics”, Materials Chemistry Communication, 7(6), (1997), 861-863.
  • Referans3 Sorokin A.B., “Phthalocyanine metal complexes in catalysis”, Chemical Reviews, 113(10), (2013), 8152-8191.
  • Referans4 Ben-Hur E., Rosenthal I., “Photosensitized inactivation of Chinese hamster cells by phthalocyanines”, Photochemistry and Photobiology, 42(2), (1985), 129—133.
  • Referans5 Bayrak R., Albay C., Koç M., Altın İ., Değirmencioğlu İ., Sökmen M., “Preparation of phthalocyanine/TiO2 nanocomposites for photocatalytic removal of toxic Cr(VI) ions Process”, Process Safety and Environmental Protection, 102, (2016), 294-302.
  • Referans6 Petritsch K., Friend R.H., Lux A., Rozenberg G., Moratti S.C., Holmes A.B., “Liquid Crystalline Phthalocyanines in Organic Solar Cells”, Synthetic Metals, 102, (1999), 1776-1777.
  • Referans7 Lü K., Zhou J., Zhou L., Chen X.S., Chan S.H., Sun Q., “Pre-combustion CO2 capture by transition metal ions embedded in phthalocyanine sheets”, The Journal of Chemical Physics, 136(23), (2012), 234703.
  • Referans18 Singh S., Aggarwal A., Bhupathiraju N. V. S. Dinesh K., Arianna G., Tiwari K., Drain C.M., “Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics”, Chemical Reviews, 115(118), (2015), 10261−10306.
  • Referans9 Snow A.W., The Porphyrin Handbook Phthalocyanines: Properties and Materials in Phthalocyanine Aggregation, Vol.17, K.M. Kadish, K.M. Smith, R. Guilard Eds. New York, Academic Press, 2003, pp. 129-176.
  • Referans10 Lukyanets E.A., Nemykin V.N., “The key role of peripheral substituents in the chemistry of phthalocyanines and their analogs”, Journal of Porphyrins and Phthalocyanines, 14(01), (2010), 1-40.
  • Referans11 Qi Z-L., Cheng Y-H., Xu Z., Chen M-L, “Recent Advances in Porphyrin-Based Materials for Metal Ions Detection”, International Journal of Molecular Science 21, (2020), 5839- 5866.
  • Referans12 Ishii K., Kobayashi N., in The Porphyrin Handbook, ed. K. M. Kadish, K. M. Smith, R. Guiard, Academic Press, New York, 2003, vol. 16, pp.1–42.
  • Referans13 Janczak J., Kubiak R., “From 1,3-dicyanobenzene to 3-cyanobenzamide—its molecular structure in the gas-phase and in the crystal”, Journal of Molecular Structure, 644 (2003), 13-21.
  • Referans14 Janczak J., Śledź M., Kubiak R., “Catalytic trimerization of 2- and 4-cyanopyridine isomers to the triazine derivatives in presence of magnesium phthalocyanine”, Journal of Molecular Structure, 659, (2003), 71-79.
  • Referans15 McKewon N.B., “Phthalocyanine Materials: Synthesis, Structure and Function”, Cambridge University Press, Cambridge, 1998.
  • Referans16 Loutfy, R.O., Hor, A.M., DiPaola-Baranyi, G., Hsiao, C.K. “Electrophotographic Photoreceptors Incorporating Aggregated Phthalocyanines”, Journal of Imaging Science, 29(3), (1985), 116-121.
  • Referans17 Khe N.C., Aizawa M., Kaishi N.K., “The Use of Magnesium Phthalocyanine Compound as Electrophotographic Receptor Available for Laser Diode Recording”, 1986(3), (1986), 393- 401.
  • Referans18 Herbst W., Hunger K., Industrial Organic Pigments: Production, Properties, Applications, Wiley-VCH, New York, 1993.
  • Referans19 Loutfy R.O., McIntre L.F., “Photoelectrochemical solar energy conversion by polycrystalline films of phthalocyanine” Solar Energy Materials, 6(4), (1982), 467-479.
  • Referans20 Loutfy R.O.,“High-conversion polymerization of fluorescence probes. 1. Polymerization of methyl methacrylate”, Macromolecules, 14, (1981), 270-275.
  • Referans21 Ghosh A.K., Morel D.L., Feng T., Shaw R.F., Rowe C.A., “Photovoltaic and rectification properties of Al/Mg phthalocyanine/Ag Schottky‐barrier cells”, Journal of Applied Physics, 45, (1974), 230-236.
  • Referans22 Bayona A.M.D.P., Mroz P., Thunshelle C., Hamblin M.R., Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers, Chemical Biology & Drug Design, 89(2), (2017), 192-206.
  • Referans23 Soares A.R.M. , Tomé J.P.C. , Neves M.G.P.M.S., Tomé A.C., Cavaleiro J.A.S. , Torres T., “Synthesis of water-soluble phthalocyanines bearing four or eight d-galactose units”, Carbohydrate Research, 344(4), (2009), 507-510.
  • Referans24 Kandaz M. , Özkaya A.R., Koca A., Salih B., “Water and alcohol-soluble octakis-metalloporphyrazines bearing sulfanyl polyetherol substituents: synthesis, spectroscopy, and electrochemistry”, Dyes and Pigments, 74(2), (2007), 483-489.
  • Referans25 Nishida M., Horiuchi H., Momotake A., Nishimura Y., Hiratsuka H., Arai T., “Singlet molecular oxygen generation by water-soluble phthalocyanine dendrimers with different aggregation behavior”, Journal of Porphyrins and Phthalocyanines, 15, (2011), 47-53.
  • Referans26 Janczak J., Idemori Y.M., “Synthesis, crystal structure and characterisation of aquamagnesium phthalocyanine—MgPc(H2O). The origin of an intense near-IR absorption of magnesium phthalocyanine known as ‘X-phase’ ”, Polyhedron, 22(9), (2003), 1167-1181.
  • Referans27 Taştemel A., Karaca B.Y., Durmuş M., Bulut M., “Photophysical and photochemical properties of novel metallophthalocyanines bearing 7-oxy-3-(m-methoxyphenyl) coumarin groups”, Journal of Luminescence 168, (2015), 163–171.
  • Referans28 Pişkin Mehmet, “The novel 2,6-dimethoxyphenoxy substituted phthalocyanine dyes having high singlet oxygen quantum yields”, Polyhedron. 104, (2016), 17-24.
  • Referans29 Kharisov B.I., Blanco L.M., Torres-Martinez L.M., García-Luna A., “Electrosynthesis of Phthalocyanines: Influence of Solvent”, Industrial & Engineering Chemistry Research, 38(8) (1999) 2880-2887.
  • Referans30 Stillman M.J., Nyokong T., Phthalocyanines Properties and Applications, vol. 1, C. C. Leznoff and A. B. P Lever, Eds., New York, Wiley-VCH Publishers,1989, ch. 3, pp. 133–289.
  • Referans31 Enkelkamp H., Nolte R.J.M.,” Molecular materials based on crown ether functionalized phthalocyanines”, Journal of Porphyrins and Phthalocyanines, 4(5), (2000), 454-459.
  • Referans32 Dominquez D.D., Snow A.W., Shirk J.S., Pong R.G.S., “Polyethyleneoxide‐capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation”, Journal of Porphyrins and Phthalocyanines, 5(7), (2001), 582-592.
  • Referans33 Nyokong T.,“Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines”, Coordination Chemistry Reviews, 251(13-14), (2007), 1707-1722.
  • Referans34 Tuhl A., Chidawanayika W., Ibrahim H. M., Al-Awadi N., Litwinski C., Nyokong T., Behbehani H., Manaa H., Makhseed S., “Tetra and octa(2,6-di-iso-propylphenoxy)-substituted phthalocyanines: a comparative study among their photophysicochemical properties”, Journal of Porphyrins and Phthalocyanines Vol. 16(01), (2012), 163-174.
  • Referans35 Kobayashi N., Ogata H., Nonaka N., Luk'yanets E.A., “Effect of Peripheral Substitution on the Electronic Absorption and Fluorescence Spectra of Metal‐Free and Zinc Phthalocyanines”, Chemistry—A European Journal, 9(20), (2003), 5123-5134
Year 2021, Volume: 9 Issue: Special 1, 58 - 64, 30.04.2021
https://doi.org/10.51354/mjen.884756

Abstract

Project Number

FBA-2021-3355

References

  • Referans1 Ingram D.J.E., Bennett J.E., “Paramagnetic resonance in phthalocyanine, chlorophyll, and hemoglobin derivatives”, The Journal of Chemical Physics, 22(6), (1954), 1136-1137.
  • Referans2 Tian M., Wada T., Kimura-Sudab H., Sasabea H., “Novel non-aggregated unsymmetrical metallophthalocyanines for second-order non-linear optics”, Materials Chemistry Communication, 7(6), (1997), 861-863.
  • Referans3 Sorokin A.B., “Phthalocyanine metal complexes in catalysis”, Chemical Reviews, 113(10), (2013), 8152-8191.
  • Referans4 Ben-Hur E., Rosenthal I., “Photosensitized inactivation of Chinese hamster cells by phthalocyanines”, Photochemistry and Photobiology, 42(2), (1985), 129—133.
  • Referans5 Bayrak R., Albay C., Koç M., Altın İ., Değirmencioğlu İ., Sökmen M., “Preparation of phthalocyanine/TiO2 nanocomposites for photocatalytic removal of toxic Cr(VI) ions Process”, Process Safety and Environmental Protection, 102, (2016), 294-302.
  • Referans6 Petritsch K., Friend R.H., Lux A., Rozenberg G., Moratti S.C., Holmes A.B., “Liquid Crystalline Phthalocyanines in Organic Solar Cells”, Synthetic Metals, 102, (1999), 1776-1777.
  • Referans7 Lü K., Zhou J., Zhou L., Chen X.S., Chan S.H., Sun Q., “Pre-combustion CO2 capture by transition metal ions embedded in phthalocyanine sheets”, The Journal of Chemical Physics, 136(23), (2012), 234703.
  • Referans18 Singh S., Aggarwal A., Bhupathiraju N. V. S. Dinesh K., Arianna G., Tiwari K., Drain C.M., “Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics”, Chemical Reviews, 115(118), (2015), 10261−10306.
  • Referans9 Snow A.W., The Porphyrin Handbook Phthalocyanines: Properties and Materials in Phthalocyanine Aggregation, Vol.17, K.M. Kadish, K.M. Smith, R. Guilard Eds. New York, Academic Press, 2003, pp. 129-176.
  • Referans10 Lukyanets E.A., Nemykin V.N., “The key role of peripheral substituents in the chemistry of phthalocyanines and their analogs”, Journal of Porphyrins and Phthalocyanines, 14(01), (2010), 1-40.
  • Referans11 Qi Z-L., Cheng Y-H., Xu Z., Chen M-L, “Recent Advances in Porphyrin-Based Materials for Metal Ions Detection”, International Journal of Molecular Science 21, (2020), 5839- 5866.
  • Referans12 Ishii K., Kobayashi N., in The Porphyrin Handbook, ed. K. M. Kadish, K. M. Smith, R. Guiard, Academic Press, New York, 2003, vol. 16, pp.1–42.
  • Referans13 Janczak J., Kubiak R., “From 1,3-dicyanobenzene to 3-cyanobenzamide—its molecular structure in the gas-phase and in the crystal”, Journal of Molecular Structure, 644 (2003), 13-21.
  • Referans14 Janczak J., Śledź M., Kubiak R., “Catalytic trimerization of 2- and 4-cyanopyridine isomers to the triazine derivatives in presence of magnesium phthalocyanine”, Journal of Molecular Structure, 659, (2003), 71-79.
  • Referans15 McKewon N.B., “Phthalocyanine Materials: Synthesis, Structure and Function”, Cambridge University Press, Cambridge, 1998.
  • Referans16 Loutfy, R.O., Hor, A.M., DiPaola-Baranyi, G., Hsiao, C.K. “Electrophotographic Photoreceptors Incorporating Aggregated Phthalocyanines”, Journal of Imaging Science, 29(3), (1985), 116-121.
  • Referans17 Khe N.C., Aizawa M., Kaishi N.K., “The Use of Magnesium Phthalocyanine Compound as Electrophotographic Receptor Available for Laser Diode Recording”, 1986(3), (1986), 393- 401.
  • Referans18 Herbst W., Hunger K., Industrial Organic Pigments: Production, Properties, Applications, Wiley-VCH, New York, 1993.
  • Referans19 Loutfy R.O., McIntre L.F., “Photoelectrochemical solar energy conversion by polycrystalline films of phthalocyanine” Solar Energy Materials, 6(4), (1982), 467-479.
  • Referans20 Loutfy R.O.,“High-conversion polymerization of fluorescence probes. 1. Polymerization of methyl methacrylate”, Macromolecules, 14, (1981), 270-275.
  • Referans21 Ghosh A.K., Morel D.L., Feng T., Shaw R.F., Rowe C.A., “Photovoltaic and rectification properties of Al/Mg phthalocyanine/Ag Schottky‐barrier cells”, Journal of Applied Physics, 45, (1974), 230-236.
  • Referans22 Bayona A.M.D.P., Mroz P., Thunshelle C., Hamblin M.R., Design features for optimization of tetrapyrrole macrocycles as antimicrobial and anticancer photosensitizers, Chemical Biology & Drug Design, 89(2), (2017), 192-206.
  • Referans23 Soares A.R.M. , Tomé J.P.C. , Neves M.G.P.M.S., Tomé A.C., Cavaleiro J.A.S. , Torres T., “Synthesis of water-soluble phthalocyanines bearing four or eight d-galactose units”, Carbohydrate Research, 344(4), (2009), 507-510.
  • Referans24 Kandaz M. , Özkaya A.R., Koca A., Salih B., “Water and alcohol-soluble octakis-metalloporphyrazines bearing sulfanyl polyetherol substituents: synthesis, spectroscopy, and electrochemistry”, Dyes and Pigments, 74(2), (2007), 483-489.
  • Referans25 Nishida M., Horiuchi H., Momotake A., Nishimura Y., Hiratsuka H., Arai T., “Singlet molecular oxygen generation by water-soluble phthalocyanine dendrimers with different aggregation behavior”, Journal of Porphyrins and Phthalocyanines, 15, (2011), 47-53.
  • Referans26 Janczak J., Idemori Y.M., “Synthesis, crystal structure and characterisation of aquamagnesium phthalocyanine—MgPc(H2O). The origin of an intense near-IR absorption of magnesium phthalocyanine known as ‘X-phase’ ”, Polyhedron, 22(9), (2003), 1167-1181.
  • Referans27 Taştemel A., Karaca B.Y., Durmuş M., Bulut M., “Photophysical and photochemical properties of novel metallophthalocyanines bearing 7-oxy-3-(m-methoxyphenyl) coumarin groups”, Journal of Luminescence 168, (2015), 163–171.
  • Referans28 Pişkin Mehmet, “The novel 2,6-dimethoxyphenoxy substituted phthalocyanine dyes having high singlet oxygen quantum yields”, Polyhedron. 104, (2016), 17-24.
  • Referans29 Kharisov B.I., Blanco L.M., Torres-Martinez L.M., García-Luna A., “Electrosynthesis of Phthalocyanines: Influence of Solvent”, Industrial & Engineering Chemistry Research, 38(8) (1999) 2880-2887.
  • Referans30 Stillman M.J., Nyokong T., Phthalocyanines Properties and Applications, vol. 1, C. C. Leznoff and A. B. P Lever, Eds., New York, Wiley-VCH Publishers,1989, ch. 3, pp. 133–289.
  • Referans31 Enkelkamp H., Nolte R.J.M.,” Molecular materials based on crown ether functionalized phthalocyanines”, Journal of Porphyrins and Phthalocyanines, 4(5), (2000), 454-459.
  • Referans32 Dominquez D.D., Snow A.W., Shirk J.S., Pong R.G.S., “Polyethyleneoxide‐capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation”, Journal of Porphyrins and Phthalocyanines, 5(7), (2001), 582-592.
  • Referans33 Nyokong T.,“Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines”, Coordination Chemistry Reviews, 251(13-14), (2007), 1707-1722.
  • Referans34 Tuhl A., Chidawanayika W., Ibrahim H. M., Al-Awadi N., Litwinski C., Nyokong T., Behbehani H., Manaa H., Makhseed S., “Tetra and octa(2,6-di-iso-propylphenoxy)-substituted phthalocyanines: a comparative study among their photophysicochemical properties”, Journal of Porphyrins and Phthalocyanines Vol. 16(01), (2012), 163-174.
  • Referans35 Kobayashi N., Ogata H., Nonaka N., Luk'yanets E.A., “Effect of Peripheral Substitution on the Electronic Absorption and Fluorescence Spectra of Metal‐Free and Zinc Phthalocyanines”, Chemistry—A European Journal, 9(20), (2003), 5123-5134
There are 35 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Research Article
Authors

Mehmet Pişkin 0000-0002-4572-4905

Ömer Faruk Öztürk 0000-0002-4545-7149

Zafer Odabaş 0000-0002-0647-0404

Project Number FBA-2021-3355
Publication Date April 30, 2021
Published in Issue Year 2021 Volume: 9 Issue: Special 1

Cite

APA Pişkin, M., Öztürk, Ö. F., & Odabaş, Z. (2021). Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine. MANAS Journal of Engineering, 9(Special 1), 58-64. https://doi.org/10.51354/mjen.884756
AMA Pişkin M, Öztürk ÖF, Odabaş Z. Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine. MJEN. April 2021;9(Special 1):58-64. doi:10.51354/mjen.884756
Chicago Pişkin, Mehmet, Ömer Faruk Öztürk, and Zafer Odabaş. “Synthesis, Spectroscopy, and Photophysical Properties of Newly Magnesium (II) Phthalocyanine”. MANAS Journal of Engineering 9, no. Special 1 (April 2021): 58-64. https://doi.org/10.51354/mjen.884756.
EndNote Pişkin M, Öztürk ÖF, Odabaş Z (April 1, 2021) Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine. MANAS Journal of Engineering 9 Special 1 58–64.
IEEE M. Pişkin, Ö. F. Öztürk, and Z. Odabaş, “Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine”, MJEN, vol. 9, no. Special 1, pp. 58–64, 2021, doi: 10.51354/mjen.884756.
ISNAD Pişkin, Mehmet et al. “Synthesis, Spectroscopy, and Photophysical Properties of Newly Magnesium (II) Phthalocyanine”. MANAS Journal of Engineering 9/Special 1 (April 2021), 58-64. https://doi.org/10.51354/mjen.884756.
JAMA Pişkin M, Öztürk ÖF, Odabaş Z. Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine. MJEN. 2021;9:58–64.
MLA Pişkin, Mehmet et al. “Synthesis, Spectroscopy, and Photophysical Properties of Newly Magnesium (II) Phthalocyanine”. MANAS Journal of Engineering, vol. 9, no. Special 1, 2021, pp. 58-64, doi:10.51354/mjen.884756.
Vancouver Pişkin M, Öztürk ÖF, Odabaş Z. Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine. MJEN. 2021;9(Special 1):58-64.

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