SYNTHESIS, CHARACTERIZATION AND SPECTROSCOPIC PROPERTIES OF PHTHALOCYANINES BEARING UMBELLIFERONE MOIETIES

Year 2016, Volume: 2 Issue: 2, 120 - 128, 25.12.2016

Meryem Çamur Mustafa Bulut

Abstract

The preparing and structure determination of new phthalonitrile complex bearing umbelliferone substituent and its phthalocyanine derivatives [M= metal-free, zinc (II), cobalt (II), copper (II)] were made. The structures of these original complexes were characterized by infrared, proton nuclear magnetic resonance, ultraviolet-visible and mass spectroscopic methods.

Keywords

Phthalocyanine; Coumarin; Spectroscopy.

References

• [1] Sandhu, S., Bansal, Y., Silakari, O., Bansal, G., Coumarin Hybrids as Novel Therapeutic Agents, Review Article. Bioorg. Med. Chem., 22, 3806–3814, 2014.
• [2] Jain, P. K., Himanshu, J., Coumarin: Chemical and Pharmacological Profile. J. Appl. Pharm. Sci., 02, 236-240, 2012.
• [3] Azelmata, J., Fioritob, S., Taddeob, V. A., Genoveseb, S., Epifanob, F., Grenier, D., Synthesis and Evaluation of Antibacterial and Anti-inflammatory Properties of Naturally Occurring Coumarins. Phytochem. Lett., 13, 399–405, 2015.
• [4] Lin, M. H., Cheng, C. H., Chen, K. C., Lee, W. T., Wang, Y. F., Xiao, C. Q., Lin, C. W., Induction of ROS-Independent JNK-Activation-Mediated Apoptosis by a Novel Coumarin- Derivative, DMAC, in Human Colon Cancer Cells. Chem-Biol. Interact., 218, 42–49, 2014.
• [5] Srivastava, P., Vyas, V., Variya, B., Patel, P., Qureshi, G., Ghate, M., Synthesis, Antiinflammatory, Analgesic, 5-Lipoxygenase (5-LOX) Inhibition Activities, and Molecular Docking Study of 7-Substituted Coumarin Derivatives. Bioorg. Chem., 67, 130–138, 2016.
• [6] Meyler's Side Effects of Drugs (Sixteenth Edition), Coumarin anticoagulants. 702-737, 2016.
• [7] Thakur, A., Singla, R., Jaitak, V., Coumarins as Anticancer Agents: A Review on Synthetic Strategies, Mechanism of Action and SAR Studies. Eur. J. Med. Chem., 101, 476-495, 2015.
• [8] Kumar, K. A., Renuka, N., Pavithra G., Kumar, G. V., Comprehensive Review on Coumarins: Molecules of Potential Chemical and Pharmacological Interest. J. Chem. Pharm. Res., 7(9), 67-81, 2015.
• [9] Jain, V. K., Ab Initio Theoretical Reinvestigation of the Ground and Excited State Properties of Silylated Coumarins: Good Candidates for Solid State Dye Lasers and Dye-Sensitized Solar Cells. Spectrochim. Acta A, 150, 806–813, 2015.
• [10] Torres É., Sequeira, S., Parreira, P., Mendes, P., Silva, T., Lobato, K., Brites M. J., Coumarin Dye With Ethynyl Group as π-Spacer Unit for Dye Sensitized Solar Cells. J. Photoch. Photobio. A, 310, 1–8, 2015.
• [11] Van Staden, J. F., Application of Phthalocyanines in Flow- and Sequential-Injection Analysis and Microfluidics Systems: A review. Talanta, 139, 75–88, 2015.
• [12] Leznoff, C. C., Lever, A. B. P., Phthalocyanines Properties and Applications, Vols. 1-4,Weinheim: VCH, 1989-1996.
• [13] Claessens, C. G., Blau, W. J., Cook, M., Hanack, M., Nolte, R. J. M., Torres, T., Wöhrle, D., Phthalocyanines and Phthalocyanine Analogues: The Quest for Applicable Optical Properties. Monats. Chem., 132, 3-11, 2001.
• [14] Liu, J. Y., Li, J., Yuan, X., Wang, W. M., Xue, J. P., In Vitro Photodynamic Activities of Zinc (II) Phthalocyanines Substituted With Pyridine Moieties. Photodiagn. Photodyn., 13, 341– 343, 2016.
• [15] Erdogan, T., Bulut, M., Çamur, M., Novel Phthalocyanines Bearing 7-Oxy-3-(3,5- difluorophenyl)coumarin Moieties: Synthesis, Characterization, Photophysical and Photochemical Properties. J. Photoch. Photobio. A., 300, 6–14, 2015.
• [16] Çamur, M., Durmus, M., Özkaya, A. R., Bulut, M., Synthesis, Photophysical, Photochemical and Electrochemical Properties of Crown Ether Bearing Coumarin Substituted Phthalocyanines. Inorg. Chim. Acta, 383, 287–299, 2012.
• [17] Esenpınar, A. A., Bulut, M., Synthesis and characterization of metal-free and metallophthalocyanines with four pendant coumarinthio/oxy-substituents. Dyes Pigm., 76, 249-255, 2008.
• [18] Perrin, D. D., Armarego, W. L. F., Purification of Laboratory Chemicals, Second Ed., Oxford: Pergamon Press, 1989.
• [19] Young, J. G., Onyebuagu, W., Synthesis and Characterization of Di-disubstituted Phthalocyanines. J. Org. Chem., 55, 2155-2159, 1990.
• [20] Nyokong, T., Structure and Bonding: Functional Phthalocyanine Molecular Materials, Springer. Berlin. First Ed., 135, 45-88, 2010.