Abstract
The synthesis of peripherally and non-peripherally substituted erbium phthalocyanines with cyclohexylphenoxyl or phenylphenoxyl fragments by the template condensation of substituted phthalonitrile and erbium chloride in boiling isoamyl alcohol was studied. The role of the influence of the substituents in the macrocycle on the yield of the product was revealed. The change in the spectra of the synthesized compounds in various solvents was studied.
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Ö. Bekaroğlu, Y. Bian, G. Bottari, X. Cai, G. de la Torre, U. Hahn, N. Ishikawa, J. Jiang, N. Kobayashi, X. Li, Y. Liu, J.-Y. Liu, P.-C. Lo, Q. Luo, D. K. P. Ng, T. Nyokong, H. Tian, T. Torres, H. Wang, H. Wu, S. Yoshimoto, Y. Zhang, Functional Phthalocyanine Molecular Materials, Springer Science, Berlin, 2010, 135, 325 pp.
N. B. McKeown, Phthalocyanine Materials: Synthesis, Structure, and Function, Cambridge University Press, Cambridge, 1998, 211 pp.
A. L. Thomas, Phthalocyanine Research and Applications, CRC Press, Boca Raton, 1990, 204 pp.
O. I. Koifman, T. A. Ageeva, I. P. Beletskaya, A. D. Averin, A. A. Yakushev, L. G. Tomilova, T. V. Dubinina, A. Yu. Tsivadze, Yu. G. Gorbunova, A. G. Martynov, D. V. Konarev, S. S. Khasanov, R. N. Lyubovskaya, T. N. Lomova, V. V. Korolev, E. I. Zenkevich, T. Blaudeck, Ch. von Borczyskowski, D. R. T. Zahn, A. F. Mironov, N. A. Bragina, A. V. Ezhov, K. A. Zhdanova, P. A. Stuzhin, G. L. Pakhomov, N. V. Rusakova, N. N. Semenishyn, S. S. Smola, V. I. Parfenyuk, A. S. Vashurin, S. V. Makarov, I. A. Dereven’kov, N. Zh. Mamardashvili, T. S. Kurtikyan, G. G. Martirosyan, V. A. Burmistrov, V. V. Aleksandriiskii, I. V. Novikov, D. A. Pritmov, M. A. Grin, N. V. Suvorov, A. A. Tsygankov, A. Yu. Fedorov, N. S. Kuzmina, A. V. Nyuchev, V. F. Otvagin, A. V. Kustov, D. V. Belykh, D. B. Berezin, A. B. Solovieva, P. S. Timashev, E. R. Milaeva, Yu. A. Gracheva, M. A. Dodokhova, A. V. Safronenko, D. B. Shpakovsky, S. A. Syrbu, Yu. A. Gubarev, A. N. Kiselev, M. O. Koifman, N. Sh. Lebedeva, E. S. Yurina, Macroheterocycles, 2020, 13, 311.
A. Kumar, V. K. Vashistha, D. K. Das, Coord. Chem. Rev., 2021, 431, 213678.
A. S. Malyasova, E. A. Kostrova, I. G. Abramov, V. E. Maizlish, O. I. Koifman, Russ. Chem. Bull., 2021, 70, 2405; DOI: https://doi.org/10.1007/s11172-021-3360-7.
G. F. M. Pereira, T. T. Tasso, Inorgan. Chim. Acta, 2021, 120271.
B. D. Zheng, J. Ye, X. Q. Zhang, N. Zhang, M. T. Xiao, Coord. Chem. Rev., 2021, 447, 214155.
N. Sh. Lebedeva, R. S. Kumeev, G. A. Al’per, A. S. Vashurin, T. V. Tararykina, J. Solution Chem., 2007, 36, 793.
A. S. Vashurin, T. V. Tikhomirova, V. E. Maizlish, Russ. J. Inorg. Chem., 2015, 60, 379.
W. L. Chan, C. Xie, W. S. Lo, J. C. G. Bünzli, W. K. Wong, K. L. Wong, Chem. Soc. Rev., 2021, 50, 12189.
V. E. Pushkarev, L. G. Tomilova, V. N. Nemykin, Coord. Chem. Rev., 2016, 319, 110.
E. Tokunaga, S. Mori, Y. Sumii, N. Shibata, ACS Omega, 2018, 3, 10912.
E. A. Safonova, A. G. Martynov, S. E. Nefedov, G. A. Kirakosyan, Y. G. Gorbunova, A. Y. Tsivadze, Inorg. Chem., 2016, 55, 2450.
I. A. Belogorokhov, Y. V. Ryabchikov, E. V. Tikhonov, V. E. Pushkarev, M. O. Breusova, L. G. Tomilova, D. R. Khokhlov, Semiconductors, 2008, 42, 321.
T. Tikhomirova, K. Nalimova, A. Kerner, A. Vashurin, S. Znoyko, J. Porphyr. Phthalocyanines, 2019, 23, 575.
A. Botnar, T. Tikhomirova, K. Nalimova, M. Razumov, A. Vashurin, J. Mol. Struct., 2020, 1205, 127626.
F. Lu, X. Sun, R. Li, D. Liang, P. Zhu, C. F. Choi, J. Jiang, New J. Chem., 2004, 28, 1116.
Y. Horii, Y. Horie, K. Katoh, B. K. Breedlove, M. Yamashita, Inorg. Chem., 2018, 57, 565.
T. V. Tikhomirova, A. A. Filippova, D. K. Govorova, G. P. Shaposhnikov, A. S. Vashurin, Russ. J. Gen. Chem., 2018, 88, 1188.
T. V. Tikhomirova, A. A. Filippova, D. K. Govorova, G. P. Shaposhnikov, A. S. Vashurin, Macroheterocycles, 2018, 11, 35.
A. Botnar, T. Tikhomirova, K. Kazaryan, A. Bychkova, V. Maizlish, I. Abramov, A. Vashurin, J. Mol. Struct., 2021, 1238, 130438.
G. Shaposhnikov, V. Kulinich, V. Maizlish, Modifitsirovannye ftalotsianiny i ikh strukturnye analogi [Modified Phthalocyanines and Their Structural Analogs], URSS, Krasand, Moscow, 2012, 480 pp. (in Russian).
D. B. Brown, in Practical Handbook of Spectroscopy, Routledge, London, 2017, 944.
L. G. Tomilova, V. E. Pushkarev, T. V. Dubinina, A. Yu. Tolbin, Dostizheniya v sinteze i issledovanii svoistv ftalocianinov i ikh analogov [Achievements in Synthesis and Study of Properties of Phthalocyanines and Their Analogs], Ed. L. G. Tomilova, Izd. Mosk. Univ., Moscow, 2019, 240 pp. (in Russian).
C. Rager, G. Schmid, M. Hanack, Chem. Eur. J., 1999, 5, 280.
K. E. Sekhosana, M. Shumba, T. Nyokong, Polyhedron, 2017, 138, 154.
J. A. de Saja, M. L. Rodriguez-Mendez, Adv. Colloid Interface Sci., 2005 116, 1.
H. E. A. Ali, M. Pişkin, S. Altun, M. Durmuş, Z. Odabaş, J. Lumin., 2016, 173, 113.
A. Weissberger, E. S. Proskauer, J. A. Riddick, E. E. Toops, Organic Solvents: Physical Properties and Methods of Purification, Science Publishers Inc, New York, 1955, 520.
US Pat. 20080004391; Pat. Appl. Pub., 2008, 11/766,456. Received November 6, 2021;
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Based on the materials of the All-Russian Congress on Chemistry of Heterocyclic Compounds (October 12–16, 2021, Sochi, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 953–961, May, 2022.
This work was financially supported by the Russian Science Foundation (Project No. 17-73-20017). The study was carried out using the scientific equipment of the Center for Collective Use of the Ivanovo State University of Chemistry and Technology (No. 075-15-2021-671).
No human or animal subjects were used in this research.
The authors declare no competing interests.
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Botnar, A.A., Domareva, N.P., Kazaryan, K.Y. et al. Synthesis and spectral properties of tetraphenoxysubstituted erbium phthalocyanines containing peripheral phenyl and cyclohexyl fragments. Russ Chem Bull 71, 953–961 (2022). https://doi.org/10.1007/s11172-022-3496-0
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DOI: https://doi.org/10.1007/s11172-022-3496-0