Synthesis and Characterization of Nitrotetrasubstituted Metallophthalocyanine (Zn, Co, Ni, Cu) Derivatives
DOI:
https://doi.org/10.5281/zenodo.14582491Keywords:
Phthalocyanine, Nitrophthalocyanine, Zinc, Cobalt, Nickel, CopperAbstract
4-(2,4-dinitrophenoxy)phthalonitrile, 1, was prepared by the reaction of 4-hydroxyphthalonitrile and 1-chloro-2,4-dinitrobenzene in the presence of K2CO3. Zn(II), 2, metallophthalocyanine was synthesized by the reaction of phthalonitrile derivative with Zn(OAc)2 ·2H2O in quinoline. Co(II), 3, Ni(II), 4, and Cu(II), 5, metallophthalocyanine derivatives were synthesized by the reaction of phthalonitrile derivative 1 with CoCl2 ·6H2O, NiCl2·6H2O and CuCl2 salts in ethylene glycol, respectively. Compound 1 has been characterized by FT-IR and 1H-NMR spectroscopies. Metallophalocyanin compounds 2-5 have been characterized by the UV/Vis, and FT-IR spectroscopies.
References
H. Wu, Z. Chen, J. Zhang, F. Wu, C. He, Y. Wuab, Z. Ren, J.Mater. Chem. A., 5, 24493-24501, 2017.
A. L. Ndiaye,J. Brunet, C. Varenne, A. Pauly, J. Phys. Chem. C., 122, 21632-21643, 2018.
D. Zou, W. Zhao, B. Cui, D. Lia, D. Liu, Phys. Chem.Chem. Phys., 20, 2048-2056, 2018.
P. Brogdon, H. Cheema, J. H. Delcamp, ChemSusChem.Rev., 11, 86-103, 2018.
Z. Liu, B. Su, X. Liu, J. Han, H. Ye, . T. Shi, Z. Tang, G. Liao, Nano-Micro Lett., 1-13, 2018.
O. K. Nag, J. Naciri, J. S. Erickson, E. Oh, J. B. Delehanty, Bioconjugate Chem., 29 2701-2714, 2018.
Andres de la Escosura, M. V. Martinez-Diaz, J. Barbera, T. Torres, J. Org. Chem., 73, 1475-1480, 2008.
E. Venuti, R.G. Della Valle, I. Bilotti, A. Brillante, M. Cavallini, A. Calo, Y. H. Geerts, J. Phys. Chem. C, 115, 12150-12157, 2011.
G. de la Torre, P. Vazquez, F. Agullo-Lopez, and T. Torres, Chem. Rev. 104, 3723-3750, 2004.
S. M. O’Flaherty, S. V. Hold, M.J. Cook, T. Torres, Y. Chen, M. Hanack, W.J. Blau, Adv. Materıals Rev., 15, 19-31, 2003.
N. Nwaji, J. Mack, J. Britton, T. Nyokong, New J. Chem., 41, 2020-2028, 2017.
Z. Fredj, M. B. Ali, M. N. Abbas, E. Dempsey, Analytica Chimica Acta 1057, 98-105, 2019.
K. Sato, K. Ando,S. Okuyama,S. Moriguchi,T. Ogura,S. Totoki,H. Hanaoka,T. Nagaya,R. Kokawa, H. Takakura,M. Nishimura,Y. Hasegawa,P. L. Choyke,M. Ogawa, H. Kobayashi, ACS Cent. Sci., 4, 1559-1569, 2018.
X. Li, Bing-De Zheng, Xiao-Hui Peng, Song-Zi Li, Jia-Wen Ying, Y. Zhao, Jian-Dong Huang, J. Yoon, Coord.Chem. Rev., 379, 147-160, 2019.
D. Zhu, S. Roy, Z. Liu, H. Weller, W. J. Parak, N. Feliu, Advanced Drug Delivery Rev., 138, 117-132, 2019.
F. Yurt1, K. Ocakoglu, M. Ince, S. G. Colak, Ö. Er, H. M. Soylu, C. Gunduz, C. B. Avci, C. C. Kurt, Chem Biol Drug Des. 91, 789-796, 2018.
Ö. Bekaroğlu, Ball –Type Phthalocyanines: Synthesis and Properties, Struct Bond, 135, 105-136, 2010.
M. B. Sağlam, A. R. Özkaya, Transit. Met. Chem., 41, 605-612, 2016.
M. Ruf, A. M. Lawrence, B. C. Noll, and C. G. Pierpont, Inorg. Chem., 37, 1992-1999, 1998.
W. Lu, J. Duan, S. Ai, Chinese Chemical Letters, 389-391, 2018.
A.B.P.Lever, M.R. Hempstead, C.C.Leznoff, W.Llu, M.Melnik, W.A.Nevln and P.Seymour, Recent studies in phthalocyanine chemistry, Pure & Appl. Chem.,58, 11, 1467-1476, 1986.
S. Makarov, C. Litwinski, E. A. Ermilov, O. Suvorova, B. Röder, D. Wöhrle, Chem. Eur. J., 12, 1468-474, 2006.
A. Yu Tolbin, L. G.Tomilova, N. S. Zefirov, Russian Chemical Reviews, 77, 435-449, 2008 .
J. Kan, H. Wang,W. Sun,W. Cao,J. Tao, J. Jiang, Inorg. Chem., 52, 8505-8510, 2013.
E. Yabas¸ E. Bağda, E. Bağda, Dyes and Pigments 120, 220-227, 2015.
M. S. Ağırtaş, A. Altındal, B. Salih, S. Sayman, Ö. Bekaroğlu, Dalton Trans., 40, 3315-3324, 2011.
M. Canlıca, B. C. Ömür, B. Salih, Inorganic Chemistry Communications, 103, 75-8, 20191.
E. Doğan, M. Özer, A. Altındal, A. R. Özkaya, B. Salih, Ö. Bekaroğlu, J. Porphyrins Phthalocyanines, 20, 1320-1333, 2016.
E. A. Kuzmina, T. V. Dubinina and L. G. Tomilova, New J. Chem., 2019, 43, 9314-9327.
J. H. Zagala, S. Griveaub, J. F. Silva , T. Nyokongc, F. Bediouib, Coordination Chemistry Reviews, 254 2755–2791, 2010.
M. S. Roy, Y. S. Deol, Y. Janu, A. K. Gautam, M. Kumar, P. Balraju, G. D. Sharma, J Mater Sci: Mater Electron, 20, 984–995, 2009.
Y. Wang, J. Chen, C. Jiang, N. Ding, C. Wang, D. Li, X. Liu, Q. Zhang, Z. Li, S. Zhong, J Solid State Electrochem, 21, 947–954, 2017.
J. G. Young, W. Onyebuagu, Synthesis and characterization of di-disubstituted phthalocyanines, J. Org. Chem., 55, 2156-2158, 1990.
W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals, Butterworth/Heinemann, Tokyo, 2003.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2025 MW Journal of Science
This work is licensed under a Creative Commons Attribution 4.0 International License.