Synthesis and Characterization of Some Five-Coordinated Tetraazaporphyrin and Phthalocyanine Manganese(III) Complexes

Ekaterina N. Ovchenkova,^a Michael Hanack,^b and Tatyana N. Lomova^a@

^aInstitute of the Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, Russia

^bUniversität Tübingen, Institut für Organische Chemie, Morgenstelle 18, 72076 Tübingen, Germany

^@Corresponding author E-mail: tnl@isc-ras.ru

DOI: 10.6060/mhc2010.1.63
Macroheterocycles 2010 3(1) 63-67

Soluble pentacoordinated manganese(III) complexes with substituted tetraazaporphyrins (TAPs) containing m-trifluoromethylphenyl, p-tert-butylphenyl groups and phthalocyanines (Pcs) containing m-trifluoromethylphenyl, m-trifluoromethylphenoxy and 3,5-di-tert-butylphenoxy groups have been synthesized either by direct metallation of macrocycles (TAPMn, 1a, and PcMns, 3a and 4a) or by template cyclotetramerization of the corresponding fumaronitrile (TAPMn, 2a) and phthalonitrile (PcMn, 5a) and characterized in details.

References:

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1. The Porphyrin Handbook (Kadish K.M., Smith K.M., Guilard R., Eds.) Vol. 6, Applications: Past, Present and Future. Academic Press, 2000.

2. The Porphyrin Handbook (Kadish K.M., Smith K.M., Guilard R., Eds.) Vol. 19, Applications of Phthalocyanines. Academic Press, 2003.

3. Meunier B., Robert A., Pratviel G., Bernadou О. In: The Porphyrin Handbook (Kadish K.M., Smith K.M., Guilard R., Eds.) Academic Press, Vol. 4, Ch. 31, 2000, p. 119.

Arasasingham R.D., He G.-X., Bruce T.C. J. Am. Chem. Soc. 1993, 115, 7985.
http://dx.doi.org/10.1021/ja00071a008

5. DismukesG. C. Chem. Rev. 1996, 96, 2909.
http://dx.doi.org/10.1021/cr950053c

6. Yachandra V.K., Sauer K., Klein M.P. Chem. Rev. 1996, 96, 2927.
http://dx.doi.org/10.1021/cr950052k

7. Klyueva M.E., Korolev V.V., Arefyev I.M., Lomova T.N. J. Porphyrins Phthalocyanines 2008, 12, 584.

8. Miller J.S., Vazquez C., Calabrese J.C., McLean R.S., Epstein A.J. Adv. Mater. 1994, 6, 217.
http://dx.doi.org/10.1002/adma.19940060306

9. Senge M.O. In: The Porphyrin Handbook (Kadish K.M., Smith K.M., Guilard R., Eds.) Academic Press, Vol. 10, Ch. 61, 2000, p. 1.

10. Engel M. K. In: The Porphyrin Handbook (Kadish K.M., Smith K.M., Guilard R., Eds.) Academic Press, Vol. 20, Ch. 122, 2003, p. 1.

11. Joergensen K.A., Pedersen J.A. Acta Chim. Scand. 1991, 45, 403.
http://dx.doi.org/10.3891/acta.chem.scand.45-0403

12. Goldberg D.P., Telser J., Krzystek J., Montalban A.G., Brunel L.C., Barrett A.G.M., Hoffman B.M. J. Am. Chem. Soc. 1997, 119, 8722.
http://dx.doi.org/10.1021/ja971169o

13. Krzystek J., Telser J., Pardi L.A., Goldberg D.P., Hoffman B.M., Brunel L.C. Inorg. Chem. 1999, 38, 6121.
http://dx.doi.org/10.1021/ic9901970

14. Donzello M.P., Dini D., D'Arcangelo, Ercolani C., Zhan R., Ou Zh., Stuzhin P.A., Kadish K.M. J. Am. Chem. Soc. 2003, 125, 14190.
http://dx.doi.org/10.1021/ja0344361

15. L'Her M., Pondaven A. In: The Porphyrin Handbook (Kadish K.M., Smith K.M., Guilard R., Eds.) Academic Press, Vol. 16, Ch. 104, 2003, p. 117.
http://dx.doi.org/10.1016/B978-0-08-092390-1.50009-6

16. Dolotova O.V., Bundina N.I., Kaliya O.L., Lukyanets E.A. J. Porphyrins Phthalocyanines 1997, 1, 355.
http://dx.doi.org/10.1002/(SICI)1099-1409(199710)1:4<355::AID-JPP39>3.0.CO;2-7

17. Banfi S., Montanary F., Quici S., Barhanova S.V., Kaliya O.L., Kopranenkov V.N., Luk'yanets E.A. Tetrahedron Lett. 1995, 36, 2317.
http://dx.doi.org/10.1016/0040-4039(95)00244-7

18. Dismukes G.S. Chem. Rev. 1996, 96, 2909.
http://dx.doi.org/10.1021/cr950053c

19. Bazanov M.I., Siling S.A., Smirnoff R.P., Zharnikova N.A., Bichkivski S.K., Samoilova L.A., Kassura V.P., Pilyus N.T., Ulitina O.E., Mesheryakova V.S., Petroff A.V. Russ. J. Electrochem. 1996, 32, 1120.

20. Marinina L.E., Mikhalenko S.A., Luk`yanets E.A. Russ. J. Gen. Chem. 1973, 43, 2010.

21. Baumann T.F., Barrett A.G.M., Hoffman B.M. Inorg. Chem. 1997, 36, 5661.
http://dx.doi.org/10.1021/ic9701367

22. Plater M.J., Jeremiah A., Bourhill G. J. Chem. Soc., Perkin Trans. 1 2002, 91.
http://dx.doi.org/10.1039/B107689M

23. Stuzhin P.A., Khelevina O.G., Metelkova S.S., Berezin B.D. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1986, 29, 19 (in Russ.).

24. Vagin S., Barthel M., Dini D., Hanack M. Inorg. Chem. 2003, 42, 2683.
http://dx.doi.org/10.1021/ic0205738

25. Klueva M.E., Repina N.V., Chizhova N.V., Berezin B.D. Russ. J. Coord. Chem. 2005, 31, 19.
http://dx.doi.org/10.1007/s11173-005-0031-4

26. Boucher L. J. Coord. Chem. Rev. 1972, 7, 289.
http://dx.doi.org/10.1016/S0010-8545(00)80024-7

27. Stuzhin P.A., Hamdush M., Homborg H. Mendeleev Commun. 1997, 5, 196.
http://dx.doi.org/10.1070/MC1997v007n05ABEH000819

28. Berezin B.D., Khelevina O.G., Stuzhin P.A. Russ. J. Phys. Chem. 1985, 59, 2181.

29. Hanack M., Datz A. Chem. Ber. 1976, 119, 1281.
http://dx.doi.org/10.1002/cber.19861190417

30. Janczak J., Kubiak R., Sledz M. Polyhedron 2003, 22, 2689.
http://dx.doi.org/10.1016/S0277-5387(03)00361-9

31. Klyueva M.E., Kosareva O.V., Kiseleva E.N., Klyuev M.V., Lomova T.N. J. Porphyrins Phthalocyanines 2004, 8, 728.

32. Gouterman M. In: The Porphyrins. Vol. III, part A. Physical Chemistry (D. Dolphin, Ed.) Academic Press: New York, 1978, 1.

33. Vagin S., Hanack M. Eur. J. Org. Chem. 2004, 600.
http://dx.doi.org/10.1002/ejoc.200300507

34. Hanack M., Heckmann H. Eur. J. Inorg. Chem. 1998, 367.
http://dx.doi.org/10.1002/(SICI)1099-0682(199803)1998:3<367::AID-EJIC367>3.0.CO;2-5

35. Schneider T., Heckmann H., Barthel M., Hanack M. Eur. J. Org. Chem. 2001, 3055.
http://dx.doi.org/10.1002/1099-0690(200108)2001:16<3055::AID-EJOC3055>3.0.CO;2-E

36. Dini D., Yang G.Y., Hanack M. J. Chem. Phys. 2003, 119, 4857.
http://dx.doi.org/10.1063/1.1595633

37. Kondratenko N.V., Nemykin V.N., Luk'yanets E.A., Kostromina N.A., Volkov S.V., Yagupolskii L.M. J. Porphyrins Phthalocyanines 1997, 1, 341.
http://dx.doi.org/10.1002/(SICI)1099-1409(199710)1:4<341::AID-JPP37>3.0.CO;2-K

38. Kondratenko N.V., Tretyakova I.N., Luk'yanets E.A., Volkov S.V., Orlova R.K., Nemykin V.N., Yagupolskii L.M. Dyes Pigments 1999, 41, 101.
http://dx.doi.org/10.1016/S0143-7208(98)00066-7

39. Akopov D.A., Akopova O.B. Russ. J. Struct. Chem. 2002, 43, 1139.
http://dx.doi.org/10.1023/A:1023667216047

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