Synthesis of Tri(4-tritylphenoxy)- and Hexa(4-methylphenoxy)-Substituted Hemihexaphyrazines

Elena A. Danilova,^a Natalia V. Bumbina,^b and Mikhail K. Islyaikin^a@

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

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

^@Corresponding author E-mail: islyaikin@isuct.ru

DOI: 10.6060/mhc2011.1.10

New representatives of hemihexaphyrazines bearing bulky substituents were synthesized by condensation of 2,5-diamino-1,3,4-thiadiazole with products derived in situ from interaction of 4-(4-tritylphenoxy)- or 4,5-bis(4-methylphenoxy)phthalonitriles with sodium alkoxides in methanol-butanol mixture. Target compounds purified by column chromatography were characterized by elemental analysis, UV-vis, IR, ¹H NMR spectroscopy and mass spectrometry.

References:

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1. Sessler J.L., Seidel D., Vivian A.E., Scot B.L., Keogh D.W. Angew. Chem. Int. Ed. Engl. 2001, 40, 591-594.
http://dx.doi.org/10.1002/1521-3773(20010202)40:3<591::AID-ANIE591>3.0.CO;2-0

2. Sessler J.L., Melfi P.J., Pantos G.D. Coord. Chem. Rev. 2006, 250, 816-843.
http://dx.doi.org/10.1016/j.ccr.2005.10.007

3. Sessler J.L., Gale P. Anion Receptor Chemistry. W-S. Cho – RSC Publishing, 2006. 400 p. – ISBN: 978-0-85404-974-5.

4. Sessler J.L., Weghorn S.J. Expanded, Contracted and Isomeric Porphyrins. New York: Pergamon, 1997. 520 p.

5. Sessler J.L., Gebauer A., Weghorn S.J. Expanded Porphyrins. In: The Porphyrin Handbook (K.M. Kadish, K.M. Smith, R. Guilard, Edrs.) San Diego CA: Academic Press, 2000, Vol. 2, p. 55-124.

6. Lash T.D. Syntheses of Novel Porphyrinoid Chromophores. In: The Porphyrin Handbook (K.M. Kadish, K.M. Smith, R. Guilard, Edrs.) San Diego CA: Academic Press, 2000, Vol. 2, p. 125-200.

7. Jasat A., Dolphin D. Chem. Rev. 1997, 97, 2267-2340.
http://dx.doi.org/10.1021/cr950078b

8. Rio Y., Rodriguez-Morgade M.S., Torres T. Org. Biomol. Chem. 2008, 6, 1877-1894.
http://dx.doi.org/10.1039/b800617b

9. Organic Photovoltaics: Concepts and Realization (C. Brabec, V. Dyakonov, J. Parisi, N. S. Sariciftci, Eds.) Berlin: Springer-Verlag, 2003. 297 p.

10. Organic Photovoltaics: Mechanisms, Materials, and Devices (S.-S. Sun, N.S. Sariciftci, Eds.). CRC Press: Boca Raton FL, 2005. 664 p.

11. Organic Photovoltaics: Materials, Device Physics, and Manufacturing Technologies (C. Brabec, U. Scherf, V. Dyakonov, Eds.). Weinheim: Wiley-VCH, 2008. 597 p.

12. Sessler J. L., Seidel D. Angew. Chem. Int. Ed. 2003, 42, 5134-5175.
http://dx.doi.org/10.1002/anie.200200561

13. Chandrashekar T.K., Venkatraman S. Acc. Chem. Res. 2003, 36, 676-691.
http://dx.doi.org/10.1021/ar020284n

14. Latos-Grazynski L. Core-Modified Heteroanalogues of Porphyrins and Metalloporphyrins. In: The Porphyrin Handbook (K.M. Kadish, K.M. Smith, R. Guilard, Eds.) San Diego CA: Academic Press, 2000, Vol. 2, p. 361-417.

15. Misra R., Chandrashekar T.K. Acc. Chem. Res. 2008, 41, 265-279.
http://dx.doi.org/10.1021/ar700091k

16. The Porphyrin Handbook (K.M. Kadish, K.M. Smith, R. Guilard, Eds.) San Diego CA: Academic Press, 2000, Vols. 1-14.

17. The Porphyrins (D. Dolphin, Ed.). New York: Academic Press, 1978. 932 p.

18. de la Torre G., Bottari G., Hahn U., Torres T. Struct. Bond. 2010, 135, 1-44.
http://dx.doi.org/10.1007/978-3-642-04752-7_1

19. Rodríguez-Morgade M.S., Cabezón B., Esperanza S., Torres T. Chem. Eur. J. 2001, 7, 2407-2413.
http://dx.doi.org/10.1002/1521-3765(20010601)7:11<2407::AID-CHEM24070>3.0.CO;2-1

20. Danilova E.A., Islyaikin M.K. Synthesis and Properties of tert-Butylsubstituted Macroheterocyclic Compounds and their Complexes with Metals. In: Uspekhi Khimii Porfirinov [Advances in Porphyrin Chemistry] (Golubchikov О.A., Ed.) Chemistry Research Institute, St.-Petersburg University: St.-Petersburg, 2004, Vol. 4, 356–375 (in Russ.).

21. Eckert A.K., Trukhina O.N., Rodríguez-Morgade M.S., Danilova E.A., Islyaikin M.K., Torres T. Mend. Comm., 2010, 20, 192-194.
http://dx.doi.org/10.1016/j.mencom.2010.06.002

22. Danilova E.A., Melenchuk T.V., Trukhina O.N., Zakharov A.V., Islyaikin M.K. Macroheterocycles 2010, 3, 33-37.

23. Zakharov A.V., Shlykov S.A., Danilova E.A., Krasnov A.V., Islyaikin M.K., Girichev G.V. Phys. Chem. Chem. Phys. 2009, 11, 8570-8579.
http://dx.doi.org/10.1039/b905436g

24. Zakharov A.V., Shlykov S.A., Bumbina N.V., Danilova E.A., Krasnov A.V., Islyaikin M.K., Girichev G.V. Chem. Comm. 2008, 3573-3575.
http://dx.doi.org/10.1039/b804308f

25. Trukhina O.N., Rodréguez-Morgade M.S., Wolfrum S., Caballero E., Snejko N., Danilova E.A., Gutiérrez-Puebla E., Islyaikin M.K., Guldi D.M., Torres T. J. Am. Chem. Soc. 2010, 132, 12991-12999.
http://dx.doi.org/10.1021/ja104577d

26. Bumbina N.V., Danilova E.A., Sharunov V.S., Filimonov S.I., Abramov I.G., Islyaikin M.K. Mend. Comm. 2008, 18, 289-290.
http://dx.doi.org/10.1016/j.mencom.2008.09.022

27. Danilova E.A., Islyaikin M.K., Kolesnikov N.A., Melenchuk T.V. Patent RF № 2313523. B.I., 2007, № 36.

28. Mikhailenko S.A., Korobkova E.V., Lukyanets E.A. Russ. J. Org. Chem. 1992, 6, 3-6.

29. Plakhtinsky V.V., Kaninsky P.S., Mironov G.S., Yasinsky O.A., Abramov I.G. Zh. Org. Khim. 1992, 28, 1232-1235. (in Russ.).

30. Yelkin I.A. Synthesis and Properties of Phthalocyanine Metallocomplexes and Macroheterocyclic Compounds with Substituents, Containing Triphenylmethyl Groups. Diss. Cand. Chem. Sci., Ivanovo, 2002. 133 p. (in Russ.)

31. Islyaikin M.K., Danilova E.A., Yagodarova L.D., Rodrigues-Morgade S.M., Torres T. Org. Letters 2001, 3, 2153-2156.
http://dx.doi.org/10.1021/ol015924l

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