Synthesis and Isolation of 2,9,17,23-Tetrakis[(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy]phthalocyanine and Its Magnesium(II) and Zinc(II) Complexes

Andrey V. Ziminov,^@ Marina A. Furman, Evgeny V. Borisov, Nikita S. Seravin, and Stanislav M. Ramsh

Saint-Petersburg State Institute of Technology (Technical University), 190013 Saint-Petersburg, Russian Federation

^@Corresponding author E-mail: ziminov@inbox.ru

DOI: 10.6060/mhc160856z

Macroheterocycles 2016 9(4) 387-394

The synthesis of novel phthalocyanine containing four (3,5-dimethyl-1H-pyrazol-1-yl)phenoxy groups and its complexes with magnesium and zinc is reported. The practically pure C_S regioisomers of peripheral substituted phthalocyanines were separated and isolated by column chromatography with good yields. The structure and symmetry of synthesized phthalocyanines were confirmed by ¹H NMR, ¹³C NMR, IR, UV-Vis, and MS spectral data. Influence of metals and reaction conditions on the isolation of practically pure C_S regioisomers were discussed. Aggregation properties of phthalocyanines were investigated in DMF in different concentration ranges.

References:

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1. Chemistry of Synthetic Dyes (Venkataraman K., Ed.), Leningrad: Khimiya, 1957, Vol. 2, pp. 1278-1304 (in Russ.)

2. Stepanov B.I. Introduction to the Сhemistry and Technology of Organic Dyes, Moscow: Khimiya, 1984. pp. 520-546 (in Russ.)

3. Wohrle D., Suvorova O., Gerdes R., Bartels O., Lapok L., Baziakina N., Makarov S., Slodek A. J. Porphyrins Phthalocyanines 2004, 8, 1020-1041.
https://doi.org/10.1142/S1088424604000398

4. McKeown N.B. Phthalocyanine Materials: Synthesis, Structure and Function. Cambridge: Cambridge University Press, 1998. 211 p.

5. Zhang Y., Cai X., Bian Y., Jiang J. Organic Semiconductors of Phthalocyanine Compounds for Field Effect Transistors (FETs). In: Functional Phthalocyanine Molecular Materials (Jiang J., Ed.), Berlin: Springer-Verlag Berlin Heidelberg, 2010, pp. 275-321.
https://doi.org/10.1007/978-3-642-04752-7_9

6. Ali H., van Lier J.E. Porphyrins and Phthalocyanines as Photosensitizers and Radiosensitizers. In: Handbook of porphyrin science (Kadish K.M., Smith K.M., Guilard R., Eds.), Singapore: World Scientific Publishing Co. Pte. Ltd., 2010, Vol. 4, pp. 1-119.
https://doi.org/10.1142/9789814280228_0016

7. Lukyanets E.A. J. Porphyrins Phthalocyanines 1999, 3, 424-432.
https://doi.org/10.1002/(SICI)1099-1409(199908/10)3:6/7<424::AID-JPP151>3.0.CO;2-K

8. Bonnett R. Chem. Soc. Rev. 1995, 24, 19-33.
https://doi.org/10.1039/cs9952400019

9. Allen C.M., Sharman W.M., van Lier J.E. J. Porphyrins Phthalocyanines 2001, 5, 161-169.
https://doi.org/10.1002/jpp.324

10. Moreira L.M., dos Santos F.V., Lyon J.P., Maftoum-Costa M., Pacheco-Soares C., Soares da Silva N. Aust. J. Chem. 2008, 61, 741–754.
https://doi.org/10.1071/CH08145

11. Martinez-Diaz M.V., Torres T. On the Significance of Phthalocyanines in Solar Cells. In: Handbook of porphyrin science (Kadish K.M., Smith K.M., Guilard R., Eds.), Singapore: World Scientific Publishing Co. Pte. Ltd., 2010, Vol. 10, pp. 141-181.
https://doi.org/10.1142/9789814307246_0017

12. Bayrak R., Akcay H.T., Durmus M., Degirmencioglu I. J. Organomet. Chem. 2011, 696, 3807-3815.
https://doi.org/10.1016/j.jorganchem.2011.09.002

13. Ranyuk E., Cauchon N., Klarskov K., Guerin B., van Lier J.E. J. Med. Chem. 2013, 56, 1520-1534.
https://doi.org/10.1021/jm301311c

14. Saka E.T., Gol C., Durmus M., Kantekin H., Biyiklioglu Z. J. Photochem. Photobiol. A: Chem 2012, 241, 67-78.
https://doi.org/10.1016/j.jphotochem.2012.05.023

15. Kobayashi N., Ogata H., Nonaka N., Luk'yanets E.A. Chem. Eur. J. 2003, 9, 5123-5134.
https://doi.org/10.1002/chem.200304834

16. Ali H., van Lier J.E. Chem. Rev. 1999, 99, 2379-2450.
https://doi.org/10.1021/cr980439y

17. Akcay H.T., Piskin M., Demirbas U., Bayrak R., Durmus M., Mentese E., Kantekin H. J. Organomet. Chem. 2013, 745-746, 379-386.
https://doi.org/10.1016/j.jorganchem.2013.08.029

18. Karimi A.R., Bayat F. Tetrahedron Lett. 2013, 54, 45-48.
http://dx.doi.org/10.1016/j.tetlet.2012.10.071

19. Nas A., Kantekin H., Durmus M., Gumrukcuoglu N. J. Lumin. 2014, 154, 15-21.
https://doi.org/10.1016/j.jlumin.2014.03.058

20. Bayrak R., Karaoglu K., Unver Y., Sancak K., Dumludag F., Degirmencioglu I. J. Organomet. Chem. 2012, 712, 57-66.
https://doi.org/10.1016/j.jorganchem.2012.04.010

21. Youssef T.E., Alhamed Y.A., Al-Shahrani S.S., Ali K.A. Rev. Chim. (Bucharest) 2014, 65(5), 560-564.

22. Youssef T.E., Al-Turaif H., Baleanu D. Rev. Chim. (Bucharest) 2014, 65(11), 1266-1270.

23. Demirbas U., Piskin M., Bayrak R., Unluer D., Dugdu E., Durmus M., Kantekin H. Synth. Met. 2016, 219, 76-82.
https://doi.org/10.1016/j.synthmet.2016.05.008

24. Wierzchowski M., Sobotta L., Skupin-Mrugalska P., Kruk J., Jusiak W., Yee M., Konopka K., Duzgunes N., Tykarska E., Gdaniec M., Mielarek J., Goslinski T. J. Inorg. Biochem. 2013, 127, 62-72.
https://doi.org/10.1016/j.jinorgbio.2013.06.012

25. Zhang X.-F., Lin Y., Guo W., Zhu J. Spectrochim Acta A. 2014, 133, 752-758.
https://doi.org/10.1016/j.saa.2014.06.063

26. Nas A., Dilber G., Durmus M., Kantekin H. Spectrochim Acta A. 2015, 1335, 55-62.
https://doi.org/10.1016/j.saa.2014.06.135

27. Yanik H., Goksel M., Yesilot S., Durmus M. Tetrahedron Lett. 2016, 57(26), 2922-2926.
https://doi.org/10.1016/j.tetlet.2016.05.080

28. Khoza P., Antunes E., Nyokong T. Polyhedron 2013, 61, 119-125.
https://doi.org/10.1016/j.poly.2013.05.046

29. Lau J.T.F., Lo P.C., Fong W.P., Ng D.K.P. J. Med. Chem. 2012, 55, 5446-5454.
https://doi.org/10.1021/jm300398q

30. Dehe D., Lothschulz C., Thiel W. New J. Chem. 2010, 34, 526-532.
https://doi.org/10.1039/b9nj00485h

31. Bayrak R., Akcay H.T., Durmus M., Degirmencioglu I. J. Organomet. Chem. 2011, 696, 3807-3815.
https://doi.org/10.1016/j.jorganchem.2011.09.002

32. Kulinich V.P., Badaukaite R.A., Tikhomirov T.V., Shaposhnikov G.P. Russ. J. Gen. Chem. 2013, 83, 744-751.
https://doi.org/10.1134/S1070363213040233

33. Fadda A.A., El-Mekawy R.E., El-Shafei A.I. J. Porphyrins Phthalocyanines 2015, 19, 753-768.
https://doi.org/10.1142/S1088424615500480

34. Ramalingam K., Thyvelikakath G.X., Berlin K.D., Chesnul R.W., Brown R.P., Durham N.N., Ealick S.E., Vander Helm D. J. Med. Chem. 1977, 20, 847-850.
https://doi.org/10.1021/jm00216a024

35. Mariappan G., Saha B.P., Sutharson L., Singh A., Garg S., Pandey L., Kumar D. Saudi Pharm. J. 2011, 19, 115-122.
https://doi.org/10.1016/j.jsps.2011.01.003

36. Gursoy A., Demiravak S., Capan G., Erol K., Vural K. Eur. J. Med. Chem. 2000, 35, 359-364.
https://doi.org/10.1016/S0223-5234(00)00117-3

37. Gawad A.N.M., Hassan G.S., Georgey H.H. Med. Chem. Res. 2012, 21, 983-994.
https://doi.org/10.1007/s00044-011-9606-4

38. Rashad A.E., Hegab M.I., Abdel-Megeid R.E., Micky J.A., Abdel-Megeid F.M.E. Bioorg. Med. Chem. 2008, 16, 7102-7106.
https://doi.org/10.1016/j.bmc.2008.06.054

39. Chauhan A., Sharma P. K., Kaushik N. Int. J. ChemTech. Res. 2011, 3, 11-17.

40. Ngubeni G.N., Britton J., Mack J., New E., Hancox I., Walker M., Nyokong T., Jones T.S., Khene S. J. Mater. Chem. C 2015, 3, 10705-10714.
https://doi.org/10.1039/C5TC01601K

41. Sommerauer M., Rager C., Hanack M. J. Am. Chem. Soc. 1996, 118, 10085-10093.
https://doi.org/10.1021/ja961009x

42. Durmus M., Yesilot S., Ahsen V. New J. Chem. 2006, 30, 675-678.
https://doi.org/10.1039/B600196C

43. Hanack M., Meng D., Beck A., Sommerauer M., Subramanian L.R. J. Chem Soc., Chem. Commun. 1993, 1, 58-60.
https://doi.org/10.1039/c39930000058

44. Rager G., Schmid G., Hanack M. Chem. Eur. J. 1999, 5, 280-288.
https://doi.org/10.1002/(SICI)1521-3765(19990104)5:1<280::AID-CHEM280>3.0.CO;2-0

45. Lunardi C.N., Rotta J.C.G., Tedesco A.C. J. Porphyrins Phthalocyanines 2003, 7, 493-499.
https://doi.org/10.1142/S1088424603000628

46. Bai M., Zhang Y., Song R., Han S., Wan P., Zhang C. Dyes and Pigments 2013, 97, 469-474.
https://doi.org/10.1016/j.dyepig.2013.01.016

47. Cespendes-Guirao F.J., Martin-Gomis L., Fernandez-Lazaro F., Sastre-Santos A. J. Porphyrins Phthalocyanines 2009, 13, 266-274.
https://doi.org/10.1142/S108842460900036X

48. Ziminov A.V., Furman M.A., Kolganova A.I., Ramsh S.M. Russ. J. Org. Chem. 2016, 52, 133-135.
https://doi.org/10.1134/S1070428016010267

49. Ziminov A.V., Pudova D.I., Kolganova A.I., Stretovich M.A., Furman M.A., Ramsh S.M. Macroheterocycles 2015, 8(1), 26-31.
https://doi.org/10.6060/mhc140721z

50. Ziminov A.V., Ramsh S.M., Terukov E.I., Trapeznikova I.N., Shamanin V.V., Yurre T.A. Semiconductors 2006, 40(10), 1131-1136.
https://doi.org/10.1134/S1063782606100022

51. Derkacheva, V.M., Lukyanets E.A. Zh. Obshch. Khim. 1980, 50(10), 2313-2318 (in Russ.).

52. Ogunsipe A., Chen J.-Y., Nyokong T. New J. Chem. 2004, 28, 822-827.
https://doi.org/10.1039/B315319C

53. Lyubimtsev A., Iqbal Z., Crucius G., Syrbu S., Taraymovich E.S., Ziegler T., Hanack M. J. Porphyrins Phthalocyanines 2011, 15, 39-46.
https://doi.org/10.1142/S1088424611002891

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Synthesis and Isolation of 2,9,17,23-Tetrakis[(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy]phthalocyanine and Its Magnesium(II) and Zinc(II) Complexes

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