Synthesis of Cu(II) and Ni(II) Phthalocyanines Bearing Nitro and 4-(1-Methyl-1-phenylethyl)phenoxy Groups

Serafima A. Znoyko,^a@ Anastasia I. Mikhailova,^a Olga B. Akopova,^b Natalia V. Bumbina,^b Nadezhda V. Usol'tseva,^b Vladimir E. Maizlish,^a and Gennady P. Shaposhnikov^a

Dedicated to Oleg A. Golubchikov on the occasion of his 70th anniversary

^aResearch Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

^bResearch Institute of Nanomaterials, Ivanovo State University, 153025 Ivanovo, Russia

^@Corresponding author E-mail: znoykosa@yandex.ru

DOI: 10.6060/mhc180169z

Macroheterocycles 2018 11(1) 41-51

Bifunctional substituted copper and nickel phthalocyanines were synthesized. These compounds were modified by introduction of sulfonic and sulfonamide groups into aryloxy fragments. Spectral and mesomorphic properties of synthesized compounds were studied.

References:

Click here to expand or collapse this section

1. Demus D., Goodby J., Gray G.W., Spiess H.-W., Vill V. Handbook of Liquid Cristals: Fundamentals, 1. WILEY-VCH Verlag GmbH, 1998.

2. Nanoscience with Liquid Crystals from Self-Organized Nanostructures to Applications (Li Q., Ed.) Kent: Springer, 2014. 420 p.

3. Chandrasekhar S., Sadashiva B.K., Suresh K.A. Pramana 1977, 9, 471–480.
https://doi.org/10.1007/BF02846252

4. Goodby J.W., Robinson P.S., Teo B.K., Cladis P.E. Mol. Cryst. Liq. Cryst. 1980, 56, 303–309.
https://doi.org/10.1080/01406568008070142

5. Piechocki C., Simon J., Skoulios A., Guillon D., Weber P. J. Amer. Chem. Soc. 1982, 104, 5245–5247.
https://doi.org/10.1021/ja00383a050

6. Li Q., Li L. Photoconducting discotic liquid crystals. In: Thermotropic Liquid Crystal (Ramamorthy A., Ed.) Dordrecht, The Netherlands: Springer, 2007. 297 p.
https://doi.org/10.1007/1-4020-5354-1_11

7. Takita Y., Hasegava H., Takahashi Y., Harada Y., Kanda A., Hanasaki N., Inabe T. J. Porphyrins Phthalocyanines 2014, 18, 814–818.
https://doi.org/10.1142/S108842461450062X

8. The Porphyrin Handbook (Kadish K.M., Smith K.M., Guilard R., Eds.) San Diego, California: Academic Press, Elsevier Science, 2003, 16, 285.

9. Basova T., Hassan A., Durmus M., Gürek A.G., Ahsen V. Coord. Chem. Rev. 2016, 310, 131–153.
https://doi.org/10.1016/j.ccr.2015.11.005

10. Tekdas D.A., Gürek A.G., Ahsen V. J. Porphyrins Phthalocyanines 2014, 18, 899–908.
https://doi.org/10.1142/S1088424614500709

11. Motoyoshi R., Suzuki A., Kikuchi K., Oku T. Synth. Met. 2009, 159, 1345–1348.
https://doi.org/10.1016/j.synthmet.2009.03.010

12. Zhou X.Q., Wang B., Han Z.X., He C.Y. Applied Mechanics and Materials 2013, 303–306, 45–48.
https://doi.org/10.4028/www.scientific.net/AMM.303-306.45

13. Rodriguez-Morgade M.S., Pelleja L., Torres T., Palomares E. J. Porphyrins Phthalocyanines 2013, 17, 814–820.
https://doi.org/10.1142/S1088424613500454

14. Makarov V.I., Vasil'chenko S.Yu., Ryabova A.V., Konov V.I., Shevchenko E.N., Lukyanets E.A., Ermakov A.E., Loschenov V.B. Russ. J. Gen. Chem. 2015, 85, 338–342.
https://doi.org/10.1134/S107036321501048X

15. Sato H., Igarashi K., Yama Y., Ichihara M., Itoh E., Ohta K. J. Porphyrins Phthalocyanines 2012, 16, 1148–1158.
https://doi.org/10.1142/S1088424612501131

16. Wöhrle D., Schnurpfeil G., Makarov S.G., Kazarin A., Suvorova O.N. Macroheterocycles 2012, 5, 191–202.
https://doi.org/10.6060/mhc2012.120990w

17. Smirnova A.I., Usol'tseva N.V., Heunrich B., Donnio B. Liq. Cryst. 2018, 45(4), 625–633.
https://doi.org/10.1080/02678292.2017.1395484

18. Usol'tseva N.V., Smirnova A.I., Kazak A.V., Giricheva N.I., Galanin N.E., Shaposhnikov G.P., Bondarchuk V.V., Yablonskii S.V. Opto-Electronic Review 2017, 25, 127–136.
https://doi.org/10.1016/j.opelre.2017.03.003

19. Kudrik E.V., Zharnikova N.V., Usol'tseva N.V., Bykova V.V., Anan'eva G.A. Liquid Crystals and their Application, Russian Journal 2004, 1(8), 80–88.

20. Takagi Y., Ohta K., Shimosugi Sh., Fujii T., Itoh E. J. Mater. Chem. 2012, 22, 14418–14425.
https://doi.org/10.1039/c2jm32284f

21. Yoshioka M., Ohta K., Yasutake M. RSC Adv. 2015, 5, 13828–13839.
https://doi.org/10.1039/C4RA13474E

22. Ishikawa A., Ohta K., Yasutake M. J. Porphyrins Phthalocyanines 2015, 19, 639–650.
https://doi.org/10.1142/S1088424615500479

23. Watarai A., Ohta K., Yasutake M. J. Porphyrins Phthalocyanines 2016, 20, 822–832.
https://doi.org/10.1142/S1088424616501005

24. Ohta K., Adachi K., Yasutake M. J. Porphyrins Phthalocyanines 2017, 21, 48–58.
https://doi.org/10.1142/S1088424617500043

25. Tschierski C. J. Mater. Chem. 1998, 8, 1485–1508.
https://doi.org/10.1039/a800946e

26. Znoiko S.A., Akopova O.B., Bumbina N.V., Maizlish V.E., Shaposhnikov G.P., Usol'tseva N.V. Macroheterocycles 2014, 7, 287–295.
https://doi.org/10.6060/mhc140930z

27. Znoiko S.A., Akopova O.B., Bumbina N.V., Usoltseva N.V., Maizlish V.E., Shaposhnikov G.P., Abramov I.G. Russ. J. Gen. Chem. 2014, 84, 708–714.
https://doi.org/10.1134/S1070363214040185

28. Znoiko S.A., Maizlish V.E., Shaposhnikov G.P., Bykova V.V., Usol'tseva N.V. Liquid Crystals and Their Application, Russ. J. 2011, 4(38), 69–79.

29. Akopova O.B., Kovaleva M.I. Liquid Crystals and Their Application, Russ. J. 2014, 14, 21–57.

30. Akopova O.B., Bulavkova M.G., Gruzdev M.S., Frolova T.V. Russ. J. Gen. Chem. 2011, 81, 714–720.
https://doi.org/10.1134/S1070363211040165

31. Akopova O.B., Akopov D.A. Computer program «CMP ChemCard» № 2012610165, 10.01.2012. (in Russ.).

32. Shishkina O.V., Maizlish V.E., Shaposhnikov G.P., Lubimtsev A.V., Smirnov R.P., Baran'sky A. Russ. J. Gen. Chem. 1997, 67, 842–845.

33. Filippova A., Vashurin A., Znoyko S., Kuzmin I., Razumov M., Chernova A., Shaposhnikov G., Koifman O. J. Mol. Struct. 2017, 1149, 17–26.
https://doi.org/10.1016/j.molstruc.2017.07.086

34. Pretsch E., Bullmann F., Affolter C. Structural Determination of Organic Compounds. Tables of Spectral Data. Berlin: Springer, 2006. 480 p.

35. Znoiko S.A., Maizlish V.E., Shaposhnikov G.P., Abramov I.G., Voron'ko M.N. Russ. J. Gen. Chem. 2007, 77, 1623–1627.
https://doi.org/10.1134/S1070363207090216

36. Znoyko S.A., Akopova О.B., Bumbina N.V., Smirnova A.I., Serova M.A., Savinova A.I., Usol'tseva N.V., Mayzlish V.E., Shaposhnikov G.P. Liquid Crystals and Their Application, Russ. J. 2016, 16(4), 59–68.
https://doi.org/10.18083/LCAppl.2016.4.59

Attachment	Size
mhc180169z.pdf	3.12 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Synthesis of Cu(II) and Ni(II) Phthalocyanines Bearing Nitro and 4-(1-Methyl-1-phenylethyl)phenoxy Groups

References: