Synthesis and some properties of 4-{4-[tris(4- octyloxyphenyl)methyl]phenoxy}phthalonitrile and copper, nickel, and cobalt phthalocyaninates on its basis

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

In four stages, by o -alkylation of phenol with 1-bromooctane, alkylation of octyloxybenzene with carbon tetrachloride, alkylation of phenol with tris(4-octyloxyphenyl)methanol, and nucleophilic substitution of the nitro group in 4-nitrophthalonitrile with tris(4-octyloxyphenyl)- 4-hydroxyphenylmethane, 4-{4-[tris(4-octyloxyphenyl)methyl]phenoxy}phthalonitrile was synthesized. Its reactions with copper(II), nickel(II), and cobalt(II) acetates in the presence of urea gave the corresponding metal phthalocyanines. The spectral properties of the obtained compounds were studied. All the phthalocyanines are not associated in chloroform at concentrations up to ~4×10-5 mol/L. They do not exhibit mesomorphic properties, but upon cooling after heating, the copper and nickel complexes pass into a glass state.

About the authors

V. A Ivakin

Ivanovo State University of Chemistry and Technology

Email: vlad.ivakin.00@mail.ru

T. A Rumyantseva

Ivanovo State University of Chemistry and Technology

N. E Galanin

Ivanovo State University of Chemistry and Technology

References

  1. Znoiko S.A., Elizarova A.P., Kustova T.V., Nakonechnaya A.N. // Chem. Chem. Tech. 2021. Vol. 64. N 4. P. 42. doi: 10.6060/ivkkt.20216404.6380
  2. de la Torre G., Claessens C.G., Torres T. // Chem. Commun. 2007. N 20. P. 2000. doi: 10.1039/B614234F
  3. Perry J.W., Mansour K., Lee I.Y.S., Wu X.L., Bedworth P.V., Chen C.T., Ng D., Marder S.R, Miles P., Wada T., Tian M., Sasabe H. // Science. 1996. Vol. 273. N 5281. P. 1533. doi: 10.1126/science.273.5281.153
  4. Durmus M., Yesilot S., Ahsen V. // New J. Chem. 2006. Vol. 30. N 5. P. 675. doi: 10.1039/B600196C
  5. Baygu Y., Capan R, Erdogan M., Ozkaya C., Acikbas Y., Kabay N., Gök Y. // Synth. Met. 2021. Vol. 280. 116870. doi: 10.1016/j.synthmet.2021.116870
  6. Sahin Z., Meunier-Prest R., Dumoulin F., Kumar A., Isci Ü., Bouvet M. // Sens. Actuators (B). 2021. Vol. 332. 129505. doi: 10.1016/j.snb.2021.129505
  7. Lo P.-C., Rodriguez-Morgade M.S., Pandey R.K., Ng D.K.P., Torres T., Dumoulin F. // Chem. Soc. Rev. 2020. Vol. 49. N 4. P. 1041. doi: 10.1039/C9CS00129H
  8. Cakir V., Arslan T. // Inorg. Chim. Acta. 2022. Vol. 530. 120678. doi: 10.1016/j.ica.2021.120678
  9. Solgun D.G., Horoz S., Agirtas M.S. // Inorg. Nano-Met. Chem. 2018. Vol. 48. N 10. P. 508. doi: 10.1080/24701556.2019.1572624
  10. Usol'tseva N., Bykova V., Ananjeva G., Zharnikova N., Kudrik E. // Mol. Cryst. Liq. Cryst. 2004. Vol. 411. N 1. P. 329. doi: 10.1080/15421400490435350
  11. Zharnikova N., Usol'tseva N., Kudrik E., Thelakkat M. // J. Mater. Chem. 2009. Vol. 19. N 20. P. 3161. doi: 10.1039/b821306b
  12. Nakamura H., Sugiyama K., Ohta K., Yasutake M. // J. Mater. Chem. (C). 2017. Vol. 5. N 29. P. 7297. doi: 10.1039/c7tc01197k
  13. Usol‘tseva N.V., Kazak AV., Luk‘yanov I.Yu., Sotsky V.V., Smirnova A.I., Yudin S.G., Shaposhnikov G.P. // Phase Trans. 2014. Vol. 87. N. 8. P. 801. doi: 10.1080/01411594.2014.893343
  14. Usol'tseva N.V., Smirnova A.I., Kazak A.V., Giricheva N.I., Galanin N.E., Shaposhnikov G.P., Bodnarchuk V.V., Yablonskii S.V. // Opto-Electronics Rev. 2017. Vol. 25. N 2. P. 127. doi: 10.1016/j.opelre.2017.03.003
  15. Брагина Н.А., Федулова И.Н., Новиков Н.В., Крутикова Е.С., Миронов А.Ф., Быкова В.В., Ананьева Г.А., Усольцева Н.В. // Макрогетероциклы. 2009. Т. 2. № 3-4. С. 228.
  16. Галанин Н.Е., Шапошников Г. П. // ЖОрХ. 2015. Т. 51. Вып. 5. С. 743
  17. Galanin N.E., Shaposhnikov G.P. // Russ. J. Org. Chem. 2015. Vol. 51. N 5. P. 727. doi: 10.1134/S1070428015050243
  18. Mohan K.T.M., Achar B.N. // J. Phys. Chem. Solids. 2006. Vol. 67. N 11. P. 2282. doi: 10.1016/j.jpcs.2006.05.005
  19. Тихомирова Т.В., Пеледина А.А., Майзлиш В.Е., Вашурин А.С., Шапошников Г.П. // ЖОХ. 2018. Т. 88. Вып. 4. С. 662
  20. Tikhomirova T.V., Peledina A.A., Maizlish V.E., Vashurin A.S., Shaposhnikov G.P. // Russ. J. Gen. Chem. 2018. Vol. 88. N 4. Р. 742. doi: 10.1134/S1070363218040199

Copyright (c) 2023 Russian Academy of Sciences

This website uses cookies

You consent to our cookies if you continue to use our website.

About Cookies