Non-Peripheral Octa- Zinc(II) Phthalocyanine: Synthesis and investigation of photosensitizer potential

Year 2022, Volume: 35 Issue: 1, 14 - 24, 01.03.2022

İrem Kulu

https://doi.org/10.35378/gujs.807707

Abstract

New compounds 3,6-bis(2-azidoethoxy)phthalonitrile and 1,4,8,11,15,18,22,25-octakis-(2-azidoethoxy) phthalocyaninato zinc(II) were synthesized and characterized by general spectroscopic methods such as UV-Vis, FT-IR, 1H NMR and mass spectrometry. Moreover, photosensitizer ability for photodynamic therapy applications; singlet oxygen photosensitizer, photodegradation and fluorescence abilities of 14,8,11,15,18,22,25-octakis-(2-azidoethoxy) phthalocyaninato zinc(II) molecule were investigated and reported. 

Keywords

Azido phthalocyanine, Fluorescence, Singlet oxygen, Photophysical, Photochemical

Supporting Institution

-

Project Number

-

Thanks

The author thanks to Prof. Dr. Mahmut DURMUS for his guidance and helpful comments.

References

• 1. Lewis, P. A., Colored Organıc Pıgments. In Applied Polymer Science: 21st Century, Craver, C. D.; Carraher, C. E., Eds. Pergamon: Oxford, 2000; pp 493-526.
• 2. de la Torre, G., Claessens, C. G.,Torres, T., "Phthalocyanines: old dyes, new materials. Putting color in nanotechnology",Chemical Communications, (20): 2000-2015,(2007).
• 3. Wong, R. C. H., Lo, P.-C.,Ng, D. K. P., "Stimuli responsive phthalocyanine-based fluorescent probes and photosensitizers",Coordination Chemistry Reviews, 379: 30-46,(2019).
• 4. Kahriman, N., Ünver, Y., Akçay, H. T., Gülmez, A. D., Durmuş, M.,Değirmencioğlu, İ., "Photophysical and photochemical study on novel axially chalcone substituted silicon (IV) phthalocyanines",Journal of Molecular Structure, 1200: 127132,(2020).
• 5. Robertson, C. A., Evans, D. H.,Abrahamse, H., "Photodynamic therapy (PDT): A short review on cellular mechanisms and cancer research applications for PDT",Journal of Photochemistry and Photobiology B: Biology, 96 (1): 1-8,(2009).
• 6. Abrahamse, H.,Hamblin, M. R., "New photosensitizers for photodynamic therapy",The Biochemical journal, 473 (4): 347-364,(2016).
• 7. De Rosa, F. S.,Bentley, M. V. L. B., "Photodynamic Therapy of Skin Cancers: Sensitizers, Clinical Studies and Future Directives",Pharmaceutical Research, 17 (12): 1447-1455,(2000).
• 8. Castano, A. P., Demidova, T. N.,Hamblin, M. R., "Mechanisms in photodynamic therapy: part one—photosensitizers, photochemistry and cellular localization",Photodiagnosis and Photodynamic Therapy, 1 (4): 279-293,(2004).
• 9. Güzel, E., "Preparation and investigation of aggregation, fluorescence and singlet oxygen generation properties of gallium and metal-free phthalocyanines",Journal of the Turkish Chemical Society Section A: Chemistry, 5 (3): 1051-1060,(2019).
• 10. Sletten, E. M.,Bertozzi, C. R., "Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality",Angewandte Chemie International Edition, 48 (38): 6974-6998,(2009).
• 11. Armarego, W. L., Purification of laboratory chemicals. Butterworth-Heinemann: (2017).
• 12. Mashazi, P., Antunes, E.,Nyokong, T., "Probing electrochemical and electrocatalytic properties of cobalt(II) and manganese(III) octakis(hexylthio)phthalocyanine as self-assembled monolayers",Journal of Porphyrins and Phthalocyanines, 14 (11): 932-947,(2010).
• 13. Qiu, Q., Shi, W., Zhao, S., Zhu, Y., Ding, Z., Zhou, S., Kairuki, M., Huang, W.,Qian, H., "Discovery to solve multidrug resistance: Design, synthesis, and biological evaluation of novel agents",Archiv der Pharmazie, 352 (10): 1900127,(2019)
• 14. Fery-Forgues, S.,Lavabre, D., "Are fluorescence quantum yields so tricky to measure? A demonstration using familiar stationery products",Journal of Chemical Education, 76 (9): 1260,(1999).
• 15. Maree, M. D., Nyokong, T., Suhling, K.,Phillips, D., "Effects of axial ligands on the photophysical properties of silicon octaphenoxyphthalocyanine",Journal of Porphyrins and Phthalocyanines, 6 (06): 373-376,(2002).
• 16. Ogunsipe, A., Chen, J.-Y.,Nyokong, T., "Photophysical and photochemical studies of zinc (II) phthalocyanine derivatives—effects of substituents and solvents",New Journal of Chemistry, 28 (7): 822-827,(2004).
• 17. Brannon, J. H.,Magde, D., "Picosecond laser photophysics. Group 3A phthalocyanines",Journal of the American Chemical Society, 102 (1): 62-65,(1980).
• 18. Ogunsipe, A.,Nyokong, T., "Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media",Journal of Photochemistry and Photobiology A: Chemistry, 173 (2): 211-220,(2005).
• 19. Seotsanyana-Mokhosi, I., Kuznetsova, N.,Nyokong, T., "Photochemical studies of tetra-2, 3-pyridinoporphyrazines",Journal of Photochemistry and Photobiology A: Chemistry, 140 (3): 215-222,(2001).
• 20. Engelkamp, H.,Nolte, R. J., "Molecular materials based on crown ether functionalized phthalocyanines",Journal of Porphyrins and Phthalocyanines, 4 (05): 454-459,(2000).
• 21. Ertem, B., Yalazan, H., Güngör, Ö., Sarkı, G., Durmuş, M., Saka, E. T.,Kantekin, H., "Synthesis, structural characterization, and investigation on photophysical and photochemical features of new metallophthalocyanines",Journal of Luminescence, 204: 464-471,(2018).
• 22. Gurol, I., Durmus, M., Ahsen, V.,Nyokong, T., "Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines",Dalton Trans, (34): 3782-91,(2007).
• 23. Saka, E. T., Gol, C., Durmus, M., Kantekin, H.,Biyikhoglu, Z., "Photophysical, photochemical and aggregation behavior of novel peripherally tetra-substituted phthalocyanine derivatives",Journal of Photochemistry and Photobiology a-Chemistry, 241: 67-78,(2012).
• 24. Gürol, İ., Gümüş, G., Tarakci, D. K., Güngör, Ö., Durmuş, M.,Ahsen, V., "Photophysical and photochemical properties of fluoroether-substituted zinc(II) and titanium(IV) phthalocyanines",Journal of Porphyrins and Phthalocyanines, 22 (01n03): 46-55,(2018).
• 25. Nyokong, T.,Ahsen, V., Photosensitizers in medicine, environment, and security. Springer Science & Business Media: (2012).