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Some Properties of an Unmetalled phthalocyanine Obtained by Chance at Low Temperature

Year 2020, Volume: 7 Issue: 3, 875 - 882, 30.10.2020
https://doi.org/10.18596/jotcsa.807291

Abstract

A novel tetrasubstituted metal-free phthalocyanine bearing phthalonitrile groups on the peripheral positions was synthesized accidentally by the cyclotetramerization reaction of the 4,4’-(1,3-phenylenebis(oxy))diphthalonitrile. For photodynamic therapy (PDT) application was described photophysical properties including fluorescence quantum yield (ΦF), fluorescence lifetime (τF), triplet state lifetime (τT) and triplet quantum yield (ΦT) and photochemical properties including singlet oxygen quantum yield (Φf) and photodegradation quantum yield (Φd) as well as magnetic circular dichroism (MCD) properties. The ΦT of phthalocyanine compound value was found 0.81. The obtained lifetime (τT) was 40 μs for metal-free Pc.

Supporting Institution

Research Fund of the Yildiz Technical University

Project Number

Project No: 2012-01-02-KAP12

Thanks

This work was supported by the Tubitak-BİDEB-2219 International Postdoctoral Research Scholarship Programme, Applying Number: 1059B191401081 and the Research Fund of the Yildiz Technical University (Project No: 2012-01-02-KAP12). The author is thankful to thank Prof. Kenneth K. Suslick and Prof. Tebello Nyokong for providing me the grant and the facilities in the lab during the research.

References

  • 1. Braun A, Tcherniac J. Uber die Producte der Einwirkung von Acetanhydrid auf Phatalamid, Ber. Deutsch. Chem. Ges., 40, 1907; 40: 2709- 2714.
  • 2. Leznoff CC, Lever ABP. (Eds.),Phthalocyanines: Properties and applications, C.C. VCH Publishers, New York, (1989, 1993, 1993, 1996); 1-4.
  • 3. Kadish KM, Smith KM, Guilard R. (Eds.), The Porphyrin Handbook: Applications of Phthalocyanines, The Porphyrin Handbook, Academic Press, New York 2000; 19.
  • 4. de la Torre G, Vásquez P, Agulló-López F, Torres T. Chem. Rev. 2004; 104: 3723.
  • 5. Rella R, Serra A, Siciliano P, Tepore A, Troisi L, Valli L. Thin Solid Films. 1996; 284-285:870.
  • 6. Armund F, Ferez H, Fouriaux S, Araspin O, Pradeau JP, Claessens CG, Maya EM, Vásquez P, Torres T. Synthetic Metals. 1999; 102: 1476.
  • 7. Snow AW, Barger WR, Klusty M, Wohltjen H, Jarvis NL, Langmuir 1986; 2: 513.
  • 8. Rosenthal I. Photochem. Photobiol. 1991; 53: 859.
  • 9. Spikes JD. J. Photochem. Photobiol. B 1990:6: 259.
  • 10. Brown SG, Tralau CJ, Coleridge-Smith PD, Akdemir DT, Wieman TJ, Br. J. Cancer. 1986; 54: 43.
  • 11. Bonnett R, in Chemical Aspects of Photodynamic Therapy, D. Phillips (Ed.),Gordon and Breach Science, Canada, 2000.
  • 12. Wöhrle D, Suvorova O, Gerdes R, Bartels O, Lapok L, Baziakina N, Makarov S, Slodek A. J. Porphyrins Phthalocyanines.2004; 8: 1020.
  • 13. Mele G, Sole RD, Vasapollo G, García-López E, Palmisano L, Schiavello M.J. Catalysis. 2003; 217: 334.
  • 14. Sehlotho N, Nyokong T. J. Mol. Catal. A: Chem. 2004; 209: 51.
  • 15. Tolbin AY, Ivanov AV, Tomilova LG, Zefirov NS, Mendeleev Commun. 2002; 12: 96.
  • 16. Tolbin AY, Ivanov AV, Tomilova LG, Zefirov NS, J Porphyr. Phtalocyan. 2003; 7: 162.
  • 17. Bonnet R. Chemical Aspect of Photodynamic Therapy , Gordonand Breach, Amsterdam, 2000.
  • 18. Ali H, Van Lier JE. Tetrahedron Lett. 2013; 54: 2956–2959.
  • 19. Canlica M, J. Photochem. Photobiol. A Chem. 2019; 384: 112043.
  • 20. Canlica M, Omur BC, Salih B. Inorg. Chem. Comm. 2019; 103: 75.
  • 21. Greenberg S. Lever ABP, Lenoff CC, Can. J. Chem., 66, 1988, 1059.
  • 22. Keller TM, Dominguez DD, Polymer. 2005; 46: 4614.
  • 23. Kobayashi N. Lever ABP, J. Am. Chem. Soc. 1987; 109: 7433.
  • 24. Kobayashi N, Nakai K. Chem. Commun. 2007; 4077.
Year 2020, Volume: 7 Issue: 3, 875 - 882, 30.10.2020
https://doi.org/10.18596/jotcsa.807291

Abstract

Project Number

Project No: 2012-01-02-KAP12

References

  • 1. Braun A, Tcherniac J. Uber die Producte der Einwirkung von Acetanhydrid auf Phatalamid, Ber. Deutsch. Chem. Ges., 40, 1907; 40: 2709- 2714.
  • 2. Leznoff CC, Lever ABP. (Eds.),Phthalocyanines: Properties and applications, C.C. VCH Publishers, New York, (1989, 1993, 1993, 1996); 1-4.
  • 3. Kadish KM, Smith KM, Guilard R. (Eds.), The Porphyrin Handbook: Applications of Phthalocyanines, The Porphyrin Handbook, Academic Press, New York 2000; 19.
  • 4. de la Torre G, Vásquez P, Agulló-López F, Torres T. Chem. Rev. 2004; 104: 3723.
  • 5. Rella R, Serra A, Siciliano P, Tepore A, Troisi L, Valli L. Thin Solid Films. 1996; 284-285:870.
  • 6. Armund F, Ferez H, Fouriaux S, Araspin O, Pradeau JP, Claessens CG, Maya EM, Vásquez P, Torres T. Synthetic Metals. 1999; 102: 1476.
  • 7. Snow AW, Barger WR, Klusty M, Wohltjen H, Jarvis NL, Langmuir 1986; 2: 513.
  • 8. Rosenthal I. Photochem. Photobiol. 1991; 53: 859.
  • 9. Spikes JD. J. Photochem. Photobiol. B 1990:6: 259.
  • 10. Brown SG, Tralau CJ, Coleridge-Smith PD, Akdemir DT, Wieman TJ, Br. J. Cancer. 1986; 54: 43.
  • 11. Bonnett R, in Chemical Aspects of Photodynamic Therapy, D. Phillips (Ed.),Gordon and Breach Science, Canada, 2000.
  • 12. Wöhrle D, Suvorova O, Gerdes R, Bartels O, Lapok L, Baziakina N, Makarov S, Slodek A. J. Porphyrins Phthalocyanines.2004; 8: 1020.
  • 13. Mele G, Sole RD, Vasapollo G, García-López E, Palmisano L, Schiavello M.J. Catalysis. 2003; 217: 334.
  • 14. Sehlotho N, Nyokong T. J. Mol. Catal. A: Chem. 2004; 209: 51.
  • 15. Tolbin AY, Ivanov AV, Tomilova LG, Zefirov NS, Mendeleev Commun. 2002; 12: 96.
  • 16. Tolbin AY, Ivanov AV, Tomilova LG, Zefirov NS, J Porphyr. Phtalocyan. 2003; 7: 162.
  • 17. Bonnet R. Chemical Aspect of Photodynamic Therapy , Gordonand Breach, Amsterdam, 2000.
  • 18. Ali H, Van Lier JE. Tetrahedron Lett. 2013; 54: 2956–2959.
  • 19. Canlica M, J. Photochem. Photobiol. A Chem. 2019; 384: 112043.
  • 20. Canlica M, Omur BC, Salih B. Inorg. Chem. Comm. 2019; 103: 75.
  • 21. Greenberg S. Lever ABP, Lenoff CC, Can. J. Chem., 66, 1988, 1059.
  • 22. Keller TM, Dominguez DD, Polymer. 2005; 46: 4614.
  • 23. Kobayashi N. Lever ABP, J. Am. Chem. Soc. 1987; 109: 7433.
  • 24. Kobayashi N, Nakai K. Chem. Commun. 2007; 4077.
There are 24 citations in total.

Details

Primary Language English
Subjects Inorganic Chemistry
Journal Section Articles
Authors

Mevlude Canlica 0000-0002-5851-5651

Project Number Project No: 2012-01-02-KAP12
Publication Date October 30, 2020
Submission Date October 7, 2020
Acceptance Date October 13, 2020
Published in Issue Year 2020 Volume: 7 Issue: 3

Cite

Vancouver Canlica M. Some Properties of an Unmetalled phthalocyanine Obtained by Chance at Low Temperature. JOTCSA. 2020;7(3):875-82.