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Year 2018, Volume: 5 Issue: 3, 1051 - 1060, 01.09.2018
https://doi.org/10.18596/jotcsa.437645

Abstract

References

  • 1. Barr JB, Wallon SB. The chemistry of furfuryl alcohol resins. J Appl Polym Sci. 1971 May;15(5):1079–90.
  • 2. Ulbrich K, Kreitmeier P, Reiser O. Microwave- or microreactor-assisted conversion of furfuryl alcohols into 4-hydroxy-2-cyclopentenones. Synlett. 2010 Aug 28;2010(13):2037–40.
  • 3. Çimen Y, Ermiş E, Dumludağ F, Özkaya AR, Salih B, Bekaroğlu Ö. Synthesis, characterization, electrochemistry and VOC sensing properties of novel ball-type dinuclear metallophthalocyanines. Sensors Actuators, B Chem. 2014;202:1137–47.
  • 4. Jiang Y, Lu Y, Lv X, Han D, Zhang Q, Niu L, et al. Enhanced Catalytic Performance of Pt-Free Iron Phthalocyanine by Graphene Support for Efficient Oxygen Reduction Reaction. ACS Catal. 2013 Jun;3(6):1263–71.
  • 5. Karaca H, Şişman İ, Güzel E, Sezer S, Selimoğlu F, Ergezen B, et al. Thiochalcone substituted phthalocyanines for dye-sensitized solar cells: Relation of optical and electrochemical properties for cell performance. Journal of Coordination Chemistry [Internet]. 2018; Available from: 10.1080/00958972.2018.1468027
  • 6. Arıcan D, Erdoğmuş A, Koca A. Electrochromism of the Langmuir-Blodgett films based on monophthalocyanines carrying redox active metal centers. Thin Solid Films. 2014 Jan;550:669–76.
  • 7. Shilpa Harish T, Viswanath P. Annealing assisted structural and surface morphological changes in Langmuir-Blodgett films of nickel octabutoxy phthalocyanine. Thin Solid Films. 2016 Jan;598:170–6.
  • 8. Basova T V., Parkhomenko RG, Polyakov M, Gürek AG, Atilla D, Yuksel F, et al. Effect of dispersion of gold nanoparticles on the properties and alignment of liquid crystalline copper phthalocyanine films. Dye Pigment. 2016;125:266–73.
  • 9. Güzel E, Yaşa Atmaca G, Erdoğmuş A, Koçak MB. Novel sulfonated hydrophilic indium(III) and gallium(III) phthalocyanine photosensitizers: preparation and investigation of photophysicochemical properties. J Coord Chem. 2017 Aug 3;70(15):2659–70.
  • 10. Güzel E, Atsay A, Nalbantoglu S, Şaki N, Dogan AL, Gül A, et al. Synthesis, characterization and photodynamic activity of a new amphiphilic zinc phthalocyanine. Dye Pigment. 2013;97(1):238–43. 11. Detty MR, Gibson SL, Wagner SJ. Current clinical and preclinical photosensitizers for use in photodynamic therapy. J Med Chem. 2004 Jul;47(16):3897–915.
  • 12. Robertson CA, Evans DH, Abrahamse H. Photodynamic therapy (PDT): A short review on cellular mechanisms and cancer research applications for PDT. J Photochem Photobiol B Biol. 2009 Jul 17;96(1):1–8.
  • 13. Özçeşmeci I, Burat AK, Bayir ZA. Synthesis and photophysical properties of novel unsymmetrical metal-free and metallophthalocyanines. J Organomet Chem. 2014;750:125–31.
  • 14. Sevim AM, Arıkan S, Özçeşmeci İ, Gül A. Photophysical properties of anthracenylmethyloxycarbonylmethylsulfanyl-phthalocyanines. Synth Met. 2013;183:1–7.
  • 15. Yilmaz I, Gürek A, Ahsen V. Synthesis, electrochemical, and spectroelectrochemical properties of tetrakis(13,17-dioxa nonacosane-15-sulphanyl) phthalocyaninato zinc(II). Polyhedron. 2005;24(7):791–8.
  • 16. Güzel E, Çetin Ş, Günsel A, Bilgiçli AT, Şişman İ, Yarasir MN. Comparative studies of photophysical and electrochemical properties of sulfur-containing substituted metal-free and metallophthalocyanines. Res Chem Intermed. 2018;44(2):971–89.
  • 17. Akkurt B, Hamuryudan E. Enhancement of solubility via esterification: Synthesis and characterization of octakis (ester)-substituted phthalocyanines. Dye Pigment. 2008 Nov;79(2):153–8.
  • 18. Özçeşmeci İ, Özçeşmeci M, Gül A, Hamuryudan E. Synthesis and spectroscopic investigation of boronic esters of metal-free fluorinated and non-fluorinated phthalocyanines. Synth Met. 2016 Dec 1;222:344–50.
  • 19. Yaşa G, Erdoğmuş A, Uğur AL, Şener MK, Avcıata U, Nyokong T. Photophysical and photochemical properties of novel phthalocyanines bearing non-peripherally substituted mercaptoquinoline moiety. J Porphyr Phthalocyanines. 2012 Jul;16(07n08):845–54.
  • 20. Güzel E, Koca A, Koçak MB. Anionic water-soluble sulfonated phthalocyanines: microwave-assisted synthesis, aggregation behaviours, electrochemical and in-situ spectroelectrochemical characterisation. Supramol Chem. 2017 Jul 3;29(7):536–46.
  • 21. Güzel E, Güney S, Kandaz M. One pot reaction and three type products; 1(4),8(11)-15(18),22(25) adjacent azine attached as macrocyclically mono, bunk-type (dimer) and polymeric metallo phthalocyanines; Synthesis, spectroscopy, and electrochemistry. Dye Pigment. 2015;113:416–25.
  • 22. Tuncer H, Görgülü AO, Hökelek T. 4-(Furan-2-ylmethoxy)benzene-1,2-dicarbonitrile. Acta Crystallogr Sect E Struct Reports Online. 2012;68(1):o153–o153.
  • 23. Maree MD, Nyokong T, Suhling K, Phillips D. Effects of axial ligands on the photophysical properties of silicon octaphenoxyphthalocyanine. J Porphyr Phthalocyanines. 2002 Jun 9;06(06):373–6.
  • 24. Saka ET, Durmuş M, Kantekin H. Solvent and central metal effects on the photophysical and photochemical properties of 4-benzyloxybenzoxy substituted phthalocyanines. J Organomet Chem. 2011;696(4):913–24.
  • 25. Güzel E, Koca A, Gül A, Koçak MB. Microwave-assisted synthesis, electrochemistry and spectroelectrochemistry of amphiphilic phthalocyanines. Synth Met. 2015;199:372–80. 26. Bayliss NS. The Effect of the Electrostatic Polarization of the Solvent on Electronic Absorption Spectra in Solution. J Chem Phys. 1950;18(3):292.
  • 27. Gürel E, Pişkin M, Altun S, Odabaş Z, Durmuş M. Synthesis, characterization and investigation of the photophysical and photochemical properties of highly soluble novel metal-free, zinc (ii), and indium (iii) phthalocyanines substituted with 2,3,6-trimethylphenoxy moieties. Dalt Trans. 2015 Mar 17;44(13):6202–11.

Preparation and investigation of aggregation, fluorescence and singlet oxygen generation properties of gallium and metal-free phthalocyanines

Year 2018, Volume: 5 Issue: 3, 1051 - 1060, 01.09.2018
https://doi.org/10.18596/jotcsa.437645

Abstract

The synthesis, characterization, aggregation, optical, fluorescence and singlet oxygen generation properties of 2-furylmethoxy substituted gallium and metal-free phthalocyanines (2 and 3, respectively) are reported for the first time. Characterization of the novel synthesized compounds was performed with elemental analysis, ultraviolet-visible spectrophotometry, fourier transform infrared spectrometry, 1H-NMR spectroscopy and mass spectrometry. When the concentration behavior of the synthesized complexes is examined in a certain concentration range in THF, it has been shown that the phthalocyanines predominantly consist of monomeric species. Furyl-containing new phthalocyanines are quite soluble in common organic solvents and this makes them possible to be used in several important applications. Fluorescence behavior of these phthalocyanines were investigated. In this study, the metal ion’s effect on the UV-Vis and photophysical features of the MPcs is also cited. These results show that the metal in the core of the phthalocyanine is an important factor in the fluorescence behavior and quantum yield (ΦF) of the complexes. In singlet oxygen generation studies showed that the phthalocyanines containing the 2-furylmethoxy group indicated a high level of photosensitization and singlet oxygen generation capacity. Consequently, these gallium and metal-free complexes are promising photosensitizer for photodynamic therapy applications.

References

  • 1. Barr JB, Wallon SB. The chemistry of furfuryl alcohol resins. J Appl Polym Sci. 1971 May;15(5):1079–90.
  • 2. Ulbrich K, Kreitmeier P, Reiser O. Microwave- or microreactor-assisted conversion of furfuryl alcohols into 4-hydroxy-2-cyclopentenones. Synlett. 2010 Aug 28;2010(13):2037–40.
  • 3. Çimen Y, Ermiş E, Dumludağ F, Özkaya AR, Salih B, Bekaroğlu Ö. Synthesis, characterization, electrochemistry and VOC sensing properties of novel ball-type dinuclear metallophthalocyanines. Sensors Actuators, B Chem. 2014;202:1137–47.
  • 4. Jiang Y, Lu Y, Lv X, Han D, Zhang Q, Niu L, et al. Enhanced Catalytic Performance of Pt-Free Iron Phthalocyanine by Graphene Support for Efficient Oxygen Reduction Reaction. ACS Catal. 2013 Jun;3(6):1263–71.
  • 5. Karaca H, Şişman İ, Güzel E, Sezer S, Selimoğlu F, Ergezen B, et al. Thiochalcone substituted phthalocyanines for dye-sensitized solar cells: Relation of optical and electrochemical properties for cell performance. Journal of Coordination Chemistry [Internet]. 2018; Available from: 10.1080/00958972.2018.1468027
  • 6. Arıcan D, Erdoğmuş A, Koca A. Electrochromism of the Langmuir-Blodgett films based on monophthalocyanines carrying redox active metal centers. Thin Solid Films. 2014 Jan;550:669–76.
  • 7. Shilpa Harish T, Viswanath P. Annealing assisted structural and surface morphological changes in Langmuir-Blodgett films of nickel octabutoxy phthalocyanine. Thin Solid Films. 2016 Jan;598:170–6.
  • 8. Basova T V., Parkhomenko RG, Polyakov M, Gürek AG, Atilla D, Yuksel F, et al. Effect of dispersion of gold nanoparticles on the properties and alignment of liquid crystalline copper phthalocyanine films. Dye Pigment. 2016;125:266–73.
  • 9. Güzel E, Yaşa Atmaca G, Erdoğmuş A, Koçak MB. Novel sulfonated hydrophilic indium(III) and gallium(III) phthalocyanine photosensitizers: preparation and investigation of photophysicochemical properties. J Coord Chem. 2017 Aug 3;70(15):2659–70.
  • 10. Güzel E, Atsay A, Nalbantoglu S, Şaki N, Dogan AL, Gül A, et al. Synthesis, characterization and photodynamic activity of a new amphiphilic zinc phthalocyanine. Dye Pigment. 2013;97(1):238–43. 11. Detty MR, Gibson SL, Wagner SJ. Current clinical and preclinical photosensitizers for use in photodynamic therapy. J Med Chem. 2004 Jul;47(16):3897–915.
  • 12. Robertson CA, Evans DH, Abrahamse H. Photodynamic therapy (PDT): A short review on cellular mechanisms and cancer research applications for PDT. J Photochem Photobiol B Biol. 2009 Jul 17;96(1):1–8.
  • 13. Özçeşmeci I, Burat AK, Bayir ZA. Synthesis and photophysical properties of novel unsymmetrical metal-free and metallophthalocyanines. J Organomet Chem. 2014;750:125–31.
  • 14. Sevim AM, Arıkan S, Özçeşmeci İ, Gül A. Photophysical properties of anthracenylmethyloxycarbonylmethylsulfanyl-phthalocyanines. Synth Met. 2013;183:1–7.
  • 15. Yilmaz I, Gürek A, Ahsen V. Synthesis, electrochemical, and spectroelectrochemical properties of tetrakis(13,17-dioxa nonacosane-15-sulphanyl) phthalocyaninato zinc(II). Polyhedron. 2005;24(7):791–8.
  • 16. Güzel E, Çetin Ş, Günsel A, Bilgiçli AT, Şişman İ, Yarasir MN. Comparative studies of photophysical and electrochemical properties of sulfur-containing substituted metal-free and metallophthalocyanines. Res Chem Intermed. 2018;44(2):971–89.
  • 17. Akkurt B, Hamuryudan E. Enhancement of solubility via esterification: Synthesis and characterization of octakis (ester)-substituted phthalocyanines. Dye Pigment. 2008 Nov;79(2):153–8.
  • 18. Özçeşmeci İ, Özçeşmeci M, Gül A, Hamuryudan E. Synthesis and spectroscopic investigation of boronic esters of metal-free fluorinated and non-fluorinated phthalocyanines. Synth Met. 2016 Dec 1;222:344–50.
  • 19. Yaşa G, Erdoğmuş A, Uğur AL, Şener MK, Avcıata U, Nyokong T. Photophysical and photochemical properties of novel phthalocyanines bearing non-peripherally substituted mercaptoquinoline moiety. J Porphyr Phthalocyanines. 2012 Jul;16(07n08):845–54.
  • 20. Güzel E, Koca A, Koçak MB. Anionic water-soluble sulfonated phthalocyanines: microwave-assisted synthesis, aggregation behaviours, electrochemical and in-situ spectroelectrochemical characterisation. Supramol Chem. 2017 Jul 3;29(7):536–46.
  • 21. Güzel E, Güney S, Kandaz M. One pot reaction and three type products; 1(4),8(11)-15(18),22(25) adjacent azine attached as macrocyclically mono, bunk-type (dimer) and polymeric metallo phthalocyanines; Synthesis, spectroscopy, and electrochemistry. Dye Pigment. 2015;113:416–25.
  • 22. Tuncer H, Görgülü AO, Hökelek T. 4-(Furan-2-ylmethoxy)benzene-1,2-dicarbonitrile. Acta Crystallogr Sect E Struct Reports Online. 2012;68(1):o153–o153.
  • 23. Maree MD, Nyokong T, Suhling K, Phillips D. Effects of axial ligands on the photophysical properties of silicon octaphenoxyphthalocyanine. J Porphyr Phthalocyanines. 2002 Jun 9;06(06):373–6.
  • 24. Saka ET, Durmuş M, Kantekin H. Solvent and central metal effects on the photophysical and photochemical properties of 4-benzyloxybenzoxy substituted phthalocyanines. J Organomet Chem. 2011;696(4):913–24.
  • 25. Güzel E, Koca A, Gül A, Koçak MB. Microwave-assisted synthesis, electrochemistry and spectroelectrochemistry of amphiphilic phthalocyanines. Synth Met. 2015;199:372–80. 26. Bayliss NS. The Effect of the Electrostatic Polarization of the Solvent on Electronic Absorption Spectra in Solution. J Chem Phys. 1950;18(3):292.
  • 27. Gürel E, Pişkin M, Altun S, Odabaş Z, Durmuş M. Synthesis, characterization and investigation of the photophysical and photochemical properties of highly soluble novel metal-free, zinc (ii), and indium (iii) phthalocyanines substituted with 2,3,6-trimethylphenoxy moieties. Dalt Trans. 2015 Mar 17;44(13):6202–11.
There are 25 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Emre Güzel 0000-0002-1142-3936

Publication Date September 1, 2018
Submission Date June 27, 2018
Acceptance Date September 10, 2018
Published in Issue Year 2018 Volume: 5 Issue: 3

Cite

Vancouver Güzel E. Preparation and investigation of aggregation, fluorescence and singlet oxygen generation properties of gallium and metal-free phthalocyanines. JOTCSA. 2018;5(3):1051-60.

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