SYNTHESIS OF (E,E)-AZOAZOMETHINES BASED ON 4-AMINOAZOBENZENE

Liquid crystal display devices are widely used in industries such as measuring instrumentation, consumer and industrial electronics, medical equipment and others. The production of these devices is a promising and growing branch of industry in Belarus. The analysis of the liquid crystal device market suggests that the demand for film polarizers of all types (transmissive, reflective and permeable-reflective) will increase due to the constant growth of liquid crystal device manufacture and their scope expanding. Currently, manufacturers of liquid crystal devices in Belarus buy polarizers abroad, and the price is determined by the manufacturers. Obviously, the researches aimed at creating domestic film polarizers of various functional purposes and for the development of technologies for their manufacture, are relevant. 4-aminoazobenzene (aniline yellow colorant) is used in the production of more complex intermediates, dyestuffs, chemical additives to polymers, pharmaceuticals, pesticides, etc. 4-aminoazobenzene is an accessible parent compound for the synthesis of promising compounds for the development of optical materials. By reaction of 4-aminoazobenzene series with vanillin aldehydes in a medium of boiling absolute methanol in the presence of catalytic amounts of glacial acetic acid, (E,E)-azoazomethynes with 75–88 % yields were synthesized. 

1. Filippovich L. N. Spectral properties of polyvinylalcohole films containing azobenzeneazonaphtalene dyes and their mixture. Vescі Nacyanal’naj akademіі navuk Belarusі. Serya hіmіchnyh navuk = Proceedings of the National Academy of Sciences of Belarus. Chemical Series, 2005, no. 5, pp. 112–115 (in Russian).

2. Fillipovich L. N., Ariko N. G., Agabekov V. E., Malashko P. M. Spectral-polarization properties and light resistance of polyvinyl-alcohol films colored with disazo dyes. Journal of Applied spectroscopy, 2005, vol. 72, no 5, pp. 617–624. ) Doi: 10.1007/s10812-005-0123-4

3. Agabekov V., Ariko N., Filippovich L. Spectral-polarizing properties and light stability of film polarizers with azodyes // Journal of the Society for Information Display, 2006, vol. 14, no 7, pp. 627–632. Doi : 10.1889/1.2235693.

4. Filippovich L. N. Optical anisotropy of PVA films colored with dichroic dyes. Vescі Nacyanal’naj akademіі navuk Belarusі. Serya hіmіchnyh navuk = Proceedings of the National Academy of Sciences of Belarus. Chemical Series, 2006, no. 5, pp. 96–99 (in Russian).

5. Filippovich L. N. Influence of the physical structure of the film polarizers polymer matrix on their optical properties and light fastness. Molodezh’ v nauke–2007: prilozhenie k zhurnalu «Vestsi Natsyyanal’nai akademii navuk Belarusi». Ch. 3: Seriya fizik-matematicheskikh. nauk. Seriya fiziko-tekhnicheskikh nauk. Seriya khimicheskikh nauk [Youth in Science–2007 : Supplement to Proceedings of the National Academy of Sciences of Belarus. Vol. 3: Physical-Mathematical Science series. PhysicalTechnical Sciences series. Chemical series]. Minsk, 2008, pp. 321–325 (in Russian).

6. Agabekov V. E., Ariko N. G., Shahab S. N., Filippovich L. N., Malashko P. M. Influence of dichroic dye nature and physical structure of polymer on spectral and thermal properties of polarizing films. Doklady BGUIR, 2008, no. 5, pp. 109–118 (in Russian).

7. Filippovich L. N., Ariko N. G., Agabekov V. E. Optical anisotropy and photostability of polarizing films dyed with Brilliant Yellow. Journal of Applied Spectroscopy, 2009, vol. 76, no. 3, pp. 440–446. Doi: 10.1007/s10812-009-9182-2

8. Shahab S. N., Ariko N. G., Agabekov V. E., Filippovich L. N. Influence of the structure of organic dyes on heat conductivity of colored polyvinyl alcohol films. Vescі Nacyanal’naj akademіі navuk Belarusі. Serya hіmіchnyh navuk = Proceedings of the National Academy of Sciences of Belarus. Chemical Series, 2009, no. 4, pp. 58–68 (in Russian).

9. Filippovich L. N. Polarizing films for the near-UV region of the spectrum. Molodezh’ v nauke–2009: prilozhenie k zhurnalu «Vestsi Natsyyanal’nai akademii navuk Belarusi». Ch. 1: Seriya khimicheskikh nauk [Youth in Science–2009 : Supplement to Proceedings of the National Academy of Sciences of Belarus. Vol. 1: Chemical series]. Minsk, 2010, pp. 82–87 (in Russian).

10. Agabekov V., Filippovich L., Shahab S., Ariko N., Ivanova N. Optical characteristics and thermo stability of film polarizers with azodyes. Advanced Display Technologies. Proc. of the 11th Intern. symp., Yalta, Crimea, Ukraine, Sept. 8–12, 2002. San Jose, 2002. 1 electronic optical disc (CD–ROM).

11. Agabekov V., Ariko N., Ivanova N., Filippovich L., Sahahb S., Matusevich V., Kiessling A., Kowarchik R. Chemical and optical investigations of film polarizers with azodyes. Organic Optoelectronics and Photonics. Proceedings of International Symposium, 2004, vol. 5464, pp. 292–296. Doi: 10.1117/12.545149.

12. Agabekov V., Ariko N., Shahab S., Filippovich L. Anisotropy of polarizing polyvinyl alcohol films. Proc. SPIE the Intern. XV International Symposium on Advanced Display Technologies, 2007, vol. 6637, pp. 66370H. Doi: 10.1117/12.742595.

13. Agabekov V. E., Ariko N. G., Shahab S. N., Filippovich L. N. Spectral polarizing and thermal-physical properties of polyvinyl alcohol films with dichroic dyes. Khimiya i tekhnologiya novykh veshchestv i materialov: sb. nauch. tr [Chemistry and technology of new substances and materials: collection of studies]. Minsk, 2008, vol. 2, pp. 3–27 (in Russian).

14. Filippovich L. N., Ariko N. G., Shahab S. N., Agabekov V. E. Thermal stability of dichroic polarizers based on polyvinyl alcohol. Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimii: sb. nauch. tr. [Chemical reagents, chemicals and processes of low-tonnage chemistry : collection of studies]. Minsk, 2011, pp. 245–255 (in Russian).

15. Agabekov V. E., Ariko N. G., Shahab S. N., Filippovich L. N. Dichroic polarizers based on polyvinyl alcohol and diazodyes. Mezhdunarodnaya konferentsiya «HighMatTesh», Kiev, Ukraina, 15–19 okt. 2007 g.: tezisy dokladov [International conference «HighMatTesh», Kiev, Ukraine, 15–19 Oct. 2007: Book of abstracts]. Kiev, 2007, pp. 426 (in Russian).

16. Agabekov V. E., Ariko N. G., Filippovich L. N., Ivanova N. A., Kosmacheva T. G., Kulevskaya I. V., Shahab S. N., Globa I. Yu., Dayneko O. A. Technological process of preparation of dichroic film polarizers based on polyvinyl alcohol. II Mezhdunarodnaya konferentsiya po khimii i khimicheskoi tekhnologii : tez. dokl., Erevan, Resp. Armeniya, 13–17 sent. 2010 g. [II International conference on chemi stry and chemical technology : Book of abstracts, Yerevan, Republic of Armeina, 13–17 Sept. 2010]. Yerevan, 2010, pp. 158–159 (in Russian).

17. Shakhab S. N., Filippovich L. N., Ariko N. G., Agabekov V. E. Dichroic polarizers for visible and ultraviolet areas of the spectrum. Available at: https://www.researchgate.net/publication/274632568_DIHROICNYE_POLARIZATORY_ DLA_VIDIMOJ_I_ULTRAFIOLETOVOJ_OBLASTEJ_SPEKTRA

18. Filippovich L. N., Ariko N. G., Almodarresiyeh H. A., Shahab S. N., Malashko P. M., Agabekov V. E. Influence of the structure and orientational distribution of azodyes on optical anisotropy of colored PVA films. Peredovye displeinye i svetovye tekhnologii : materialy KhKh Mezhdunar. simp., Yalta, Ukraina, 8–12 okt. 2012 g. [Advanced display and light technologies: materials of XX International. simp., Yalta, Ukraine, 8–12 Oct. 2012]. Kiev, 2012, pp. 22 (in Russian).

19. Almodarresiyeh H. A., Shahab S. N., Agabekov V. E., Ariko N. G. Spectral properties of polarizing films containing mixture of dichroic dyes. Vescі Nacyanal’naj akademіі navuk Belarusі. Serya hіmіchnyh navuk = Proceedings of the National Academy of Sciences of Belarus. Chemical Series, 2013, no. 3, pp. 55–59.

20. Almodarresiyeh H. A., Shahab S. N., Agabekov V. E., Ariko N. G. Broadband dichroic polarizers. Vestnik Mskovskogo gosudarstvennogo oblastnogo universiteta. Seriya: Fizika-matematika = Bulletin MGOU. Series: Physics and mathematics, 2013, no. 1, pp. 82–90 (in Russian).

21. Almodarresiyeh H. A., Shahab S. N., Filippovich L. N., Ariko N. G., Agabekov V. E. Preparation and optical properties of broad-band polyvinyl alcohol films colored with a mixture of dichroic dyes. Doklady Natsional’noi akademii nauk Belarusi = Doklady of the National Academy of Sciences of Belarus, 2014, vol. 58, no. 1, pp. 57–61 (in Russian).

22. Agabekov V. E., Ariko N. G., Filippovich L. N, Shahab S. N., Almodarresiyeh H. A. Dichroic dyes for broadband film polarizers. Khimiya i tekhnologiya novykh veshchestv i materialov: cbornik statei [Chemistry and technology of new substances and materials : collection of studies]. Minsk, 2014, pp. 58–75 (in Russian).

23. Almodarresiyeh H.A., Shahab S., Agabekov V., Ariko N. Polarizing film for wide spectral range. The 3-rd International scientific conference of Iranian students in Belarus, Minsk, 2 June 2012. Minsk, 2012. 1 electronic optical disk (CD–ROM).

24. Filippovich L. N., Malashko P. M., Ariko N. G., Almodarresiyeh H. A., Shahab S. N., Agabekov V. E. Preparation and properties of azodyes for broadband dichroic polarizers. Khimicheskie reaktivy, reagenty i protsessy malotonnazhnoi khimii: tez. dokl. XXVI Mezhdunar. nauch.-tekhn. konf. «Reaktiv – 2012», Minsk, 2–4 okt. 2012 g. [Chemical reagents, chemicals and processes of low–tonnage chemistry : Book of abstracts of XXVI Int. sci.-tech. conf. “Reagent – 2012”, Minsk, 2–4 Oct. 2012]. Minsk, 2012, pp. 41 (in Russian).

25. Filippovich L. N., Ariko N. G., Almodarresiyeh H. A., Shahab S. N., Malashko P. M., Agabekov V. E. Influence of structure and orientational distribution of azodyes on optical anisotropy of colored PVA films. ХХ Mezhdunarodnyi simpozium «Peredovye displeinye i svetovye tekhnologii», ADLT–12: Yalta, 8–12 okt. 2012 g. [ХХ International Symposium «Advanced Display and Light Technologies», ADLT–12: Yalta, 8–12 Oct. 2012]. Yalta, 2012, pp. 22–23 (in Russian).

26. Almodarresiyeh H. A., Shahab S. N., Filippovich L. N., Ariko N. G., Agabekov V. E. Broadband dichroic polarizers. 21-i mezhdunarodnyi simpozium «Peredovye displeinye i svetovye tekhnologii», ADLT–13: Moskva, 9–12 apr. 2013 g. [21st International Symposium «Advanced Display and Light Technologies», ADLT–13: Moscow, 9–12 April. 2013]. Moscow, 2013, pp. 82 (in Russian).

27. Kustov L. M. Why organic chemistry is important for a physical chemist? Russian Journal of Organic Chemistry, 2016, vol. 52, no. 7, pp. 1072–1075. Doi: 10.1134/s1070428016070319

28. Vorozhtsov N. N. Fundamentals of the synthesis of intermediate products and dyes. Moscow, State Technical Chemical Publishing House ONTI, 1934. 534 p. (in Russian).

29. Dikusar E. A., Kozlov N. G., Tlegenov R. T., Uteniyazov K. U. Azomethins based on vanillin and vanillal. Nukus, Karakalpakstan Publ, 2007. 207 p. (in Russian).

30. Dikusar E. A., Kozlov N. G., Potkin V. I., Tlegenov R. T. Nitrogen-containing vanillin synthons in organic synthesis. Preparation, application, biological activity. Vol. 2. Nukus, Bilim, 2010. 225 p. (in Russian).

31. Dikusar E. A., Kozlov N. G., Potkin V. I., Yuvchenko A. P., Tlegenov R. T. Substituted benzaldehydes of vanillin series in organic synthesis: production, application, biological activity. Minsk, Pravo i ekonomika, 2011. 445 p. (in Russian).

32. Dikusar E. A., Potkin V. I., Kozlov N. G. Vanillin-based benzaldehydes. Synthesis of derivatives, applications and biological activity. Saarbrücken, Deutschland: LAP LAMBERT Academic Publishing GmbH & Co. KG, 2012. 604 p. (in Russian).

33. Minbaev B. U., Yashnova N. IPhysicochemical properties of Schiff bases. Alma-Ata, Science of the Kazakh SSR, 1990. 230 p. (in Rusian).

34. Schmidt M. W., Baldridge K. K., Boatz J. A., Elbert S. T., Gordon M. S., Jensen J. H., Koseki S., Matsunaga N., Nguyen K. A., Su S. J., Midus T. L., Dupnis M., Montgomery J. A. General Atomic and Molecular Electronic-Structure System. Journal of Computational Chemistry, 1993, vol. 14, no. 7, pp. 1347–1363. Doi: 10.1002/jcc.540141112

35. Huzinaga S., Andzelm J. M., Klobukowski M. Gaussian Basis Sets for Molecular Calculations. Amsterdam: Elsevier, 1984. 434 p.

36. Azarko V. A., Dikusar E. A., Potkin V. I., Kozlov N. G., Yuvchenko A. P. Film-forming, thermo- and photosensitive properties of aromatic azomethines based on vanillin. Optika neodnorodnykh struktur – 2007: materialy mezhdunarodnoi nauchno-prakticheskoi konferentsii (2–3 oktyabrya 2007 g.) [Optics of heterogeneous structures – 2007: materials of the international scientific and practical conference (October 2–3, 2007)]. Mogilev, Mogilev State University named after AA Kuleshov, 2007, pp. 27–30 (in Russian).

37. Saleem L. M. N. Tran-cis isomerization of Schiff’s bases (N-benzylideneanilines) on addition of lanthanide shift reagents. Organic Magnetic Resonance, 1982, vol. 19, no. 1, pp. 176–180. Doi: 10.1002/mrc.1270190403