Issue

Vol. 25 No. 4 (2013): Vol 25 Issue 4

Copyright (c) 2013 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Density Functional Theory Studies of Octakis(propyl) Porphyrazine and Its Fe(II) Complex

https://doi.org/10.14233/ajchem.2013.14280
Millicent K. Mongale
Department of Chemistry, School of Mathematical and Physical Sciences, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa
David A Isabirye
Department of Chemistry, School of Mathematical and Physical Sciences, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa
Mwadham M. Kabanda
Department of Chemistry, School of Mathematical and Physical Sciences, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa
Eno E. Ebenso
Department of Chemistry, School of Mathematical and Physical Sciences, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa

Corresponding Author(s) : Eno E. Ebenso

Eno.Ebenso@nwu.ac.za

Asian Journal of Chemistry, Vol. 25 No. 4 (2013): Vol 25 Issue 4

Abstract

The synthesis and characterization of metallated porphyrazine compounds is gaining increasing attention because of the numerous functionalities for this class of compounds. In this study synthesis and quantum chemical calculations (utilizing the B3LYP/6-31G(d,p) method) on 2,3,7,8,12,13,17,18-octakis(propyl)porphyrazine ligand and its iron metallated complex have been investigated to determine the metallation effects on the electronic and geometric properties of the ligand. The time-dependent density functional theory (TDDFT) approach was utilized for the analysis of the UV-visible spectra. The variation in geometric parameters, HOMO-LUMO gap, dipole moment and Mulliken atomic charges suggest that metallation induces significant geometric changes that is dependent on the spin state of iron. A comparison of porphyrazine ligand and 2,3,7,8,12,13,17,18-octakis(propyl)porphyrazine ligand suggests that alkylation has minimal influence on the geometry of the porphyrazine moiety.

Keywords

Porphyrazine synthesis DFT studies HOMO-LUMO gap
K. Mongale, M., A Isabirye, D., M. Kabanda, M., & E. Ebenso, E. (2012). Synthesis and Density Functional Theory Studies of Octakis(propyl) Porphyrazine and Its Fe(II) Complex. Asian Journal of Chemistry, 25(4), 2308–2314. https://doi.org/10.14233/ajchem.2013.14280
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. E.J. Baerends, G. Ricciardi, A. Rosa and S.J.A. van Gisbergen, Coord. Chem. Rev., 230, 5 (2002).
  2. E.G. Sakellariou, A.G. Montalban, H.G. Meunier, R.B. Ostler, G. Rumbles, A.G.M. Barrett and B.M. Hoffman, J. Photochem. Photobiol. A-Chem., 136, 185 (2000).
  3. H. Ali and J.E. van Lier, Chem. Rev., 99, 2379 (1999).
  4. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim (1995).
  5. G. De la Torre, P. Vazquez, F. Agullo-Lopez and T. Torres, J. Mater. Chem., 8, 1671 (1998).
  6. Z.-C. Sun, Y.-B. She, Y. Zhou, X.-F. Song and K. Li, Molecules, 16, 2960 (2011).
  7. J. Haber, L. Matachowski, K. Pamin and J. Poltowicz, J. Mol. Catal. A: Chem., 198, 215 (2003).
  8. O. Zakharieva, A.X. Trautwein and C. Veeger, Biophys. Chem., 88, 11 (2000).
  9. L. Bourre, G. Simonneaux, Y. Ferrand, S. Thibaut, Y. Lajat and T. Patrice, J. Photochem. Photobiol. B, 69, 179 (2003).
  10. M. Biesaga, J. Orska, D. Fiertek, J. Izdebski and M. Trojanowicz, Fresenius J. Anal. Chem., 364, 160 (1999).
  11. C.M. Drain, K.C. Russell and J.M. Lehn, Chem. Commun., 3, 337 (1996).
  12. G. Ergün, J. Chem. Res., 2008, 465 (2008).
  13. H. Akkus and A. Gül, Transition Metal Chem., 26, 689 (2001).
  14. J. Tang, L. Chen, J. Sun, K. Lv and K. Deng, Inorg. Chem. Commun., 13, 236 (2010).
  15. X. Zhang, Y. Zhang and J. Jiang, J. Mol. Struct., 673, 103 (2004).
  16. X. Zhang and J. Jiang, J. Elect. Spectrosc. Rel. Phenom., 142, 145 (2005).
  17. X. Zhang, N. Kobayashi and J. Jiang, Spectrochim. Acta A, 64, 526 (2006).
  18. Z. Liu, X. Zhang, Y. Zhang, R. Li and J. Jiang, Spectrochim. Acta A, 65, 467 (2006).
  19. V.N. Nemykin, R.G. Hadt, R.V. Belosludov, H. Mizuseki and Y. Kawazoe, J. Phys. Chem. A, 111, 12901 (2007).
  20. A. Baccouche, B. Peigne´, F. Ibersiene, D. Hammoute`ne, A. Boutarfaia, A. Boucekkine, C. Feuvrie, O. Maury, I. Ledoux and H. LeBozec, J. Phys. Chem. A, 114, 5429 (2010).
  21. D. Qi and J. Jiang, J. Phys. Chem. A, 115, 13811 (2011).
  22. K.A. Nguyen and R. Pachter, J. Chem. Phys., 114, 10757 (2001).
  23. J. Mack, Y. Asano, N. Kobayashi and M.J. Stillman, J. Am. Chem. Soc., 127, 17697 (2005).
  24. J. Fan, M. Seth, J. Autschbach and T. Ziegler, Inorg. Chem., 47, 11656 (2008).
  25. J. Autschbach, T. Ziegler, S.J.A. van Gisbergen and E.J. Baerends, J. Chem. Phys., 116, 6930 (2002).
  26. Y. Shao, L.F. Molnar, Y. Jung, J. Kussmann, C. Ochsenfeld, S.T. Brown, A.T.B. Gilbert, L.V. Slipehenko, S.V. Levehenko, D.P. O'Neill, R.A. DiStasio Jr., R.C. Lochan, T. Wang, G.J.O. Beran, N.A. Besley, J.M. Herbert, C.Y. Lin, T. Van Voorhis, S.H. Chien, A. Sodt, R.P. Steele, V.A. Rassolov, P.E. Maslen, P.P. Korambath, R.D. Adamson, B. Austin, J. Baker, E.F.C. Byrd, H. Dachsel, R.J. Doerksen, A. Dreuw, B.D. Dunietz,A.D. Dutoi, T.R. Furlani, S.R. Gwaltney, A. Heyden, S. Hirata, C.P. Hsu, G. Kedziora, R.Z. Khalliulin, P. Klunzinger, A.M. Lee, M.S. Lee, W.Z. Liang, I. Lotan, N. Nair, B. Peters, E.I. Proynov, P.A. Pieniazek, Y.M. Rhee, J. Ritchie, E. Rosta, C.D. Sherrill, A.C. Simmonett, J.E. Subotnik, H.L. Woodcock III, W. Zhang, A.T. Bell, A.K. Chakraborty, D.M. Chipman, F.J. Keil, A. Warshel, W.J. Hehre, H.F. Schaefer, J. Kong, A.I. Krylov, P.M.W. Gill and M. Head-Gordon, Phys. Chem. Chem. Phys., 8, 3172 (2010).
  27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu,A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. AlLaham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez and J.A. Pople, GAUSSIAN 03, Gaussian, Inc., Pittsburgh, PA (2003).
  28. R.P. Linstead and M. Whalley, J. Chem. Soc., 4839 (1952).
  29. J. Fitzgerald, B.S. Haggerty, A.N. Rheingold and L. May, Inorg. Chem., 31, 2006 (1992).
  30. J. Fitzgerald, W. Taylor and H. Owen, Synthesis, 686 (1991).
  31. S.J. Lange, H. Nie, C.L. Stern, A.G.M. Barrett and B. Hoffmann, Inorg. Chem., 37, 6435 (1998).
  32. T.P. Forsyth, A.G. Montalban, A.G.M. Barrett and B. Hoffmann, J. Org. Chem., 63, 331 (1998).
  33. B. Cosimelli, G. Roncucci, D. Dei, L. Fantetti, F. Ferroni, M. Ricci and D. Spinelli, Tetrahedron, 59, 10025 (2003).
  34. P. Kubát and J. Mosinger, J. Photochem. Photobiol. A, 96, 93 (1996).
  35. D.P. Goldberg, A.G. Montalban, A.J.P. White, D.J. Williams, A.G.M. Barrett and B. Hoffmann, Inorg. Chem., 37, 2873 (1998).
  36. M. Gouterman, J. Chem. Phys., 30, 1139 (1959).
  37. B.A. Hess, Jr. and L.J. Schaad, J. Am. Chem. Soc., 93, 2413 (1971).
  38. R.C. Haddon and T. Fukunaga, Tetrahedron Lett., 21, 1191 (1980).
  39. R.G. Pearson, Proc. Natl. Acad. Sci. USA, 83, 8440 (1986).
  40. R.G. Pearson, J. Am. Chem. Soc., 110, 2092 (1988).
  41. R.G. Pearson, J. Org. Chem., 54, 1423 (1989).
  42. Z. Zhou, R.G. Parr and J.F. Garst, Tetrahedron. Lett., 29, 4843 (1988).
  43. P. Zimcik, V. Novakova, M. Miletin and K. Kopecky, Macroheterocycles, 1, 21 (2008).
  44. N. Kobayashi and H. Konami, in eds.: C.C. Leznoff and A.B.P. Lever, Molecular Orbitals and Electronic Spectra of Phthalocyanine Analogues, in Phthalocyanines: Properties and Applications, VCH Publishers, New York, vol. 4 (1996).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 1 Download : 1