Theoretical study on phthalocyanine, pyrazinoporphyrazine and their complexation with Mg2+ and Zn2+

Molecular Simulation

Volumn 36, Issue 3, 2010, Pages 192-198

  Lee, A ^a   Kim, D ^a   Choi, S H ^a   Park, J W ^b   Jaung, J Y ^c   Jung, D H ^a  

^a Insilicotech Co Ltd   (South Korea)

^b The Catholic University of Korea   (South Korea)

^c Hanyang University   (South Korea)

Author keywords

Metal complex; Phthalocyanine; Pyrazinoporphyrazine; TDDFT; UV vis absorption spectra; ZINDO

Indexed keywords

ABSORPTION BAND; ABSORPTION PEAKS; BAND GAPS; BLUE-SHIFTED; COORDINATED COMPOUNDS; FRONTIER MOLECULAR ORBITALS; INTERMEDIATE NEGLECT OF DIFFERENTIAL OVERLAP; METAL COORDINATION; METAL-FREE PHTHALOCYANINE; NITROGEN ATOM; PHTHALOCYANINE; PYRAZINES; PYRROLE RING; Q BANDS; SEMI-EMPIRICAL; THEORETICAL STUDY; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; UV-VIS ABSORPTION SPECTRA;

ABSORPTION; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; LIGHT ABSORPTION; METAL COMPLEXES; METALS; MOLECULAR ORBITALS; NITROGEN COMPOUNDS; ULTRAVIOLET SPECTROSCOPY; ZINC;

COORDINATION REACTIONS;

EID: 77649136130     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020903177641     Document Type: Article

References (28)

1. L. Edwards and M. Goutermans, Porphyrins: XV. Vapor absorption spectra and stability: Phthalocyanines, J. Mol. Spec. 33 (1970), pp. 292-310.
2. E. Ough, T. Nyokong, K.A.M. Creber, and M.J. Stillman, Electrochemistry and spectroscopy of magnesium phthalocyanine. Analysis of the absorption and magnetic circular dichroism spectra, Inorg. Chem. 27 (1988), pp. 2724-2732.
3. N. Kobayashi, K. Adachi, and T. Osa, Some spectroscopic, electrochemical and spectroelectrochemical properties of tetrapyra- zinoporphyrazine and its iron and cobalt complexes, Anal. Sci. 6 (1990), pp. 449-453.
4. T. Harazono and I. Takagishi, Solvent effects on electronic states of pthalocyanines, Bull. Chem. Soc. Jpn. 66 (1993), pp. 1016-1023.
5. R. Slota and G. Dyrda, UV photostability of metal phthalocyanines in organic solvents, Inorg. Chem. 42 (2003), pp. 5743-5750.
6. K. Bayo, J.C. Mossoyan, and G.V. Ouedraogo, Preparation and analysis by UV-vis of zinc phthalocyanine complexes, Spec. Acta Part A 60 (2004), pp. 653-657.
7. T.M. Mohan and B.N. Achar, UV-visible spectral study on the stability of lead phthalocyanine complexes, J. Phys. Chem. Sol. 67 (2006), pp. 2282-2288.
8. M.G. Cory, H. Hirose, and M.C. Zerner, Calculated structures and electronic absorption spectroscopy for magnesium phthalocyanine and its anion radical, Inorg. Chem. 34 (1995), pp. 2969-2979.
9. J.O. Morley, Theoretical investigation of the structure and spectra of zinc phthalocyanines, J. Phys. Chem. 99 (1995), pp. 1928-1934.
10. A.B.J. Parusel and S. Grimme, DFT/MRCI calculations on the excited states of porphyrin, hydroporphyrins, tetrazaporphyrins and metalloporphyrins, J. Por. Phtha. 5 (2001), pp. 225-232.
11. K.A. Nguyen and R. Pachter, Ground state electronic structures and spectra of zinc complexes of porphyrin, tetraazaporphyrin, tetrabenzoporphyrin, and phthalocyanine: A density functional theory study, J. Chem. Phys. 114 (2001), pp. 10757-10767.
12. G. Ricciardi and A. Rosa, Ground and excited states of zinc phthalocyanine studied by density functional methods, J. Phys. Chem. A 105 (2001), pp. 5242-5254.
13. X. Zhou, A.M. Ren, J.K. Feng, and X.J. Liu, Theoretical studies on the one- and two-photon absorption of tetrabenzoporphyrins and phthalocyanines, Can. J. Chem. 82 (2004), pp. 19-26.
14. Z. Liu, X. Zhang, Y. Zhang, and J. Jiang, The molecular, electronic structures and IR and Raman spectra of metal-free, N,N0-dideuterio, and magnesium tetra-2,3-pyrazino-porphyrazines: Density functional calculations, Vib. Spec. 43 (2007), pp. 447-459.
15. S.F. Yuan and Z.R. Chen, Study on the prediction of visible absorption maximum of phthalocyanine compounds by semiempirical quantum methods, J. Phys. Chem. A 109 (2005), pp. 2582-2585.
16. S. Matsumoto, K. Matsuhama, and J. Mizuguchi, β Metal free phthalocyanine, Acta Cryst. C 55 (1999), pp. 131-133.
17. - (X = F, C1, Br); Crystal structure of Bis(tripheny1phosphine)iminiumchloro (phtha1ocyaninato)magnesate acetone solvate, Z. Anorg. Allg. Chem. 622 (1996), pp. 1085-1090.
18. W.R. Scheidt and W. Dow, Molecular stereochemistry of phthalo-cyanatozinc(II), J. Am. Chem. Soc. 99 (1977), pp. 1101-1104.
19. V.N. Nemykin, R.G. Hadt, R.V. Belosludov, H. Mizuseki, and Y. Kawazoe, Influence of molecular geometry, exchange-correlation functional, and solvent effects in the modeling of vertical excitation energies in phthalocyanines using time-dependent density functional theory (TDDFT) and polarized continuum model TDDFT methods: Can modern computational chemistry methods explain experimental controversies?, J. Phys. Chem. A 111 (2007), pp. 12901-12913.
20. E.G. Gal'pern, E.A. Luk'yanets, and M.G. Gal'pern, Influence of azasubstitution on the electronic absorption spectra of phthalocyanins, Russ. Chem. Bull. 9 (1973), pp. 1976-1980.
21. N. Kobayashi and H. Konami, Molecular orbitals and electronic spectra of phthalocyanine analogues, in Phthalocyanines: Properties and Applications, C.C. Leznoff and A.B.P. Lever, eds., Vol. 4, VCH Publishers, New York, NY, 1996, pp. 343-404.
22. B. Delley, From molecules to solids with the DMol3 approach, J. Chem. Phys. 113 (2000), pp. 7756-7764.
23. J.P. Perdew, K. Burke, and M. Ernzerhof, Generalized gradient approximation made simple, Phys. Rev. Lett. 77 (1996), pp. 3865-3868.
24. B. Delley, An all-electron numerical method for solving the local density functional for polyatomic molecules, J. Chem. Phys. 92 (1990), pp. 508-517.
25. M.C. Zerner, G.H. Loew, R.F. Kirchner, and U.T. Mueller-Westerhoff, An intermediate neglect of differential overlap technique for spectroscopy of transition-metal complexes. Ferrocene, J. Am. Chem. Soc. 102 (1980), pp. 589-599.
26. E.J. Bylaska, W.A. de Jong, K. Kowalski, T.P. Straatsma, M. Valiev, D. Wang, E. Aprà, T.L. Windus, S. Hirata, M.T. Hackler, Y. Zhao, P.-D. Fan, R.J. Harrison, M. Dupuis, D.M.A. Smith, J. Nieplocha, V. Tipparaju, M. Krishnan, A.A. Auer, M. Nooijen, E. Brown, G. Cisneros, G.I. Fann, H. Früchtl, J. Garza, K. Hirao, R. Kendall, J.A. Nichols, K. Tsemekhman, K. Wolinski, J. Anchell, D. Bernholdt, P. Borowski, T. Clark, D. Clerc, H. Dachsel, M. Deegan, K. Dyall, D. Elwood, E. Glendening, M. Gutowski, A. Hess, J. Jaffe, B. Johnson, J. Ju, R. Kobayashi, R. Kutteh, Z. Lin, R. Littlefield, X. Long, B. Meng, T. Nakajima, S. Niu, L. Pollack, M. Rosing, G. Sandrone, M. Stave, H. Taylor, G. Thomas, J. van Lenthe, A. Wong, and Z. Zhang, NWChem: A Computational Chemistry Package for Parallel Computers, Version 5.0, Pacific Northwest Laboratory, Richland, WA, 2006.
27. M.G. Gal'pern and E.A. Luk'yanets, Phthalocyanines and related compounds. III. Synthesis and electron absorption spectra of some nitrogen-containing heterocyclic analogs of phthalocyanine, Z. Obs. Khimi. 39 (1969), pp. 2536-2541.
28. S.V. Kudrevich, M.G. Gal'pern, and J.E. Van Lier, Octacarboxy substituted tetra(2,3-pyrazino)porphyrazines and their derivatives, Canadian patent application. (1994), 2133284.