Abstract
Chloranil through condensation reaction with vicinal diamine such as diaminomaleonitrile produced heterocyclic monomer, p-benzoquinonebis[2,3-b; 2′,3′-b′]pyrazine-5,6-dinitrile. The tetranitrile monomer was cyclo-tetramerised using lithium/pentanol and acetic acid affording the corresponding tetra p-benzoquinone bis[2,3-b; 2′,3′-b′]pyrazinoporphyrazine)]-based network polymer (2H-Pz). The tetranitril monomer was cyclo-tetramerised using metal salt and quinoline affording the corresponding porphyrazinato-metal II-based network polymers (M-Pz), M = Co, Ni or Cu. Elemental analytical results, IR and NMR spectral data of the prepared molecules are consistent with their assigned formulations. Molecular masses and metal contents of the synthesized polymers proved to be of high molecular masses which confirm the efficiency of tetramerization polymerization and complexation reactions. The prepared pyrazinoporphyrazines were used as efficient catalysts for the oxidation of thiophenol and benzylthiol to their disulfides in the presence of air atmosphere. The results of oxidation of thiophenol and benzylthiol show that after 15 min the maximum yield of the corresponding disulfides reached 95%, 91%, respectively.
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Jörg, K., Subramanian, L.R. and Michael, H., J. Porphyrins Phthalocyanines, 2000, 4: 498
Sakamoto, K., Ohno-Okumura, E., Kato, T., Watanabe, M. and Cook, M., J. Metal-Based Drugs, 2008, 2008: 1
Faust, R. and Weber, C., J. Org. Chem., 1999, 64: 2571
Wang, C.S., Bryce, M.R., Batsanov, A.S. and Howard, J.A.K., Chem. Eur. J., 1973, 10: 1679
Budd, P.M., Ghanem, B., Msayib, K., McKeown, N.B. and Tattershall, C., J. Mater. Chem., 2003, 13: 2721
Mani, N.S., Beall, L.S., White, A.J.P., Williams, D.J., Barrett, A.G.M. and Hoffman, B.M., Chem. Commun., 1994, 1943
Shindy, H.A., El-Maghraby, M.A. and Eissa, F.M., Dyes Pigm., 2006, 68: 11
Schutten, J.H. and Beelen, T.P.M., J. Molec. Catal., 1981, 10: 85
Brouwer, W.M., Fiet, P. and German, A.L., J. Molec. Catal., 1984, 22: 297
Brouwer, W.M., Traa, P.A.M., de Weerd, T.J.W., Piet, F. and German, A.L., Die Angew. Makromol., Chem., 1984, 128: 133
Arai, H. and Yashiro, M., J. Molec. Catal., 1978, 3: 427
Abdel-Razik, H.H., El-Sayed, S. and Hassen, A., J. Appl. Polym. Sci., 2011, 121: 3579
Abdel-Razik, H.H. and Mahmoud, K.H., J. Appl. Polym. Sci., 2012, 123: 1329
Kim, J., Jaung, J.Y. and Ahn, H., Macromol. Res., 2008, 16(4): 367
Jaung, J.Y., Matsuoka, M. and Fukunishi, K., Synthesis, 1998, 1998: 1347
Puigdollers, J., Voz, C., Fonrodona, M., Cheylan, S., Stella, M., Andreu, J., Vetter, M. and Alcubilla, R., J. Non-Cryst. Solids, 2006, 352: 1778
Wizel, S., Margel, S., Gedanken, A., Rojas, T.C., Fernandez, A. and Prozorov, R., J. Mater. Res., 1999, 14(10): 3913
Bruder, I., Schöneboom, J., Dinnebier, R., Ojala, A., Schäfer, S., Sens, R., Erk, P. and Weis, J., Org. Electron., 2010, 11: 377
Cory, M.G. and Zerner, M.C., Chem. Rev., 2001, 91: 813
Chen, Q., Gu, D. and Gan, F., Physica B, 1995, 212: 189
McKeown, N.B., Makhseed, S. and Budd, P.M., Chem. Commun., 2002, 2780
Iranpoor, N. and Zeynizadeh, B., Synthesis, 1999, 49
Sonavane, S.U., Chidambaram, M., Almog, J. and Sasson, Y., Tetrahedron Lett., 2007, 48: 6048
Joglekar, H., Samant, S. and Joshi, J., Water Res., 1991, 25: 135
Sadana, A. and Katzer, J., J. Catal., 1974, 35: 140
Rollman, L.D., J. Amer. Chem. Soc., 1975, 97: 2132
Alejandre, A., Medina, F., Salagre, P., Fabregat, A. and Sueiras, J.E., Appl. Catal. B: Environ., 1998, 18: 307
Hay, A.S., Adv. Polym. Sci., 1967, 4: 496
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Abdel-Razik, H.H., Asghar, B.H. & Kenawy, E. Synthesis, characterization and spectroscopic investigation of pyrazinoporphyrazine network polymer-supported metal (II)-based catalysts. Chin J Polym Sci 31, 242–250 (2013). https://doi.org/10.1007/s10118-013-1184-0
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DOI: https://doi.org/10.1007/s10118-013-1184-0