Two-electron reduction of alkyl(sulfanyl)porphyrazines: A route to free-base and peripherally metallated asymmetric porphyrazines

Dalton Transactions

Volumn , Issue 2, 2004, Pages 305-312

  Belviso, Sandra ^a   Giugliano, Anna ^a   Amati, Mario ^a   Ricciardi, Giampaolo ^a   Lelj, Francesco ^a   Scolaro, Luigi Monsù ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; COMPOSITION EFFECTS; ELECTRONS; HIGH TEMPERATURE EFFECTS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; SODIUM COMPOUNDS; SUBSTITUTION REACTIONS;

ALKYLSULFANYL PORPHYRAZINES; ASYMMETRIC PORPHYRAZINES; INTRAMOLECULAR REARRANGEMENTS; SOLVATOCHROMISM; TRICHLOROBENZENE;

SULFUR COMPOUNDS;

EID: 0742301718     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/B312495A     Document Type: Article

References (45)

1. (a) E. Rose, A. Lecas, M. Quelquejeu, A. Kossanyi and B. Boitrel, Coord. Chem. Rev., 1998, 178-180, 1408
2. (b) N. Kobayashi, Coord. Chem. Rev., 2001, 219-221, 99
3. (c) S. M. LeCours, H.-W. Guan, S. G. Di Magno, C. H. Wang and M. J. Therien, J. Am. Chem. Soc., 1996, 118, 1497
4. (d) S. Priyadarshy, M. J. Therien and D. N. Beratan, J. Am. Chem. Soc., 1996, 118, 1504
5. (e) Y. Liu, Y. Xu, D. Zhu, Y. Wade, H. Sasabe, L. Liu and W. Wang, Thin Solid Films, 1994, 244, 943
6. (f) F. Bonosi, G. Ricciardi, F. Lelj and G. Martini, J. Phys. Chem., 1994, 98, 10613
7. (g) F. Bonosi, G. Ricciardi, F. Lelj and G. Martini, Thin Solid Films, 1994, 243, 335
8. (h) Y. Liu, Y. Xu, D. Zhu and X. Zhao, Thin Solid Films, 1996, 289, 282
9. (i) R. Ricceri, G. Ricciardi, F. Lelj, G. Martini and G. Gabrielli, Thin Solid Films, 1999, 342, 277
10. (j) E. M. Maya, P. Vazquez and T. Torres, Chem.-Eur. J., 1999, 5, 2004
11. (k) A. Sastre, B. del Rey and T. Torres, J. Org. Chem., 1996, 61, 8591
12. (l) A. Sastre, M. A. Díaz-García, B. del Rey, C. Dhenaut, J. Zyss, I. Ledoux, F. Agulló-López and T. Torres, J. Phys. Chem. A, 1997, 101, 9773
13. (m) J. V. Bakboord, M. J. Cook and E. Hamuryudan J. Porphyrins Phthalocyanines, 2000, 4, 510
14. N. Kobayashi, R. Kondo, S. Nakajima and T. Osa, J. Am. Chem. Soc., 1990, 112, 9640
15. (n) N. Kobayashi, J. Porphyrins Phthalocyanines, 1999, 3, 453
16. (o) M. Geyer, F. Plenzig, J. Rauschnabel, M. Hanack, B. del Rey, A. Sastre and T. Torres, Synthesis, 1996, 1139.
17. S. Belviso, G. Ricciardi, F. Lelj, L. Monsù Scolaro, A. Bencini and C. Carbonera, J. Chem. Soc., Dalton Trans., 2001, 1143.
18. +, affortding the neutral porphyrazine, a behaviour that closely mimic that of the hemiporphyrinogen: (a) G. Solari, E. Solari, G. Lemercier, C. Floriani, A. Chiesi-Villa and C. Rizzoli, Inorg. Chem., 1997, 36, 2691
19. (b) A. Rosa, G. Ricciardi, M. Rosi, A. Sgamellotti and C. Floriani, J. Chem. Soc., Dalton Trans., 1993, 24, 3759.
20. (a) D. N. Mason, G. B. Deacon, L. J. Yellowlees and A. Bond, Dalton Trans., 2003, 890
21. (b) H. A. Boucher, G. A. Lawrence, P. A. Lay, A. M. Sargeson, A. M. Bond, D. F. Sangster and J. C. Sullivan, J. Am. Chem. Soc., 1983, 105, 4652
22. (c) R. Cini, F. P. Fanizzi, F. P. Intini and G. Natile, J. Am. Chem. Soc, 1991, 113, 7805
23. (d) G. Bandoli, P. A. Caputo, F. P. Intini, M. F. Sivo and G. Natile, J. Am. Chem. Soc., 1997, 119, 10370.
24. (a) S. Belviso, G. Ricciardi and F. Lelj, J. Mater. Chem., 2000, 10, 297
25. (b) F. Lelj, G. Morelli, G, Ricciardi, A. Roviello and A. Sirigu, Mol. Cryst., Liq. Cryst., 1992, 12, 941.
26. K. Andersen, M. Anderson, O. P. Anderson, S. Baum, T. F. Baumann, L. S. Beall, W. E. Broderick, A. S. Cook, D. M. Eichhorn, D. Goldberg, H. Hope, W. Jarrell, S. J. Lange, Q. J. McCubbin, N. S. Mani, T. Miller, A. Garrido Montalban, M. S. Rodriguez-Morgade, S. Lee, H. Nie, M. M. Olmstead, M. Sabat, J. W. Sibert, C. Stern, A. J. P. White, D. B. G. Williams, D. J. Williams and A. G. M. Barrett and B. M. Hoffman, J. Heterocycl. Chem., 1998, 35, 1013, and references therein.
27. (a) P. S. Pregosin, Coord. Chem. Rev., 1982, 44, 247
28. (b) P. S. Pregosin, Annu. Rep. NMR Spectrosc., 1986, 17, 285-349.
29. A. J. Bard and L. R. Faulkner, in Electrochemical Methods, Fundamentals and Applications, New York, John Wiley & Sons, 1980.
30. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzeewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98 (Revision A.11), Gaussian, Inc., Pittsburgh, PA, 2001.
31. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
32. A. Nicklass, M. Dolg, H. Stoll and H. Preuss, J. Chem. Phys., 1995, 102, 8942, and references therein.
33. T. H. Dunning, Jr. and P. J. Hay, in Modern Theoretical Chemistry, ed. H. F. Schaefer, III, Plenum, New York, 1976, vol. 3, 1.
34. G. Schaftenaar and J. H. Noordik, J. Comput.-Aid. Mol. Des., 2000, 14, 123 (www.cmbi.kun.nl/∼schaft/molden/molden.html).
35. J. Stillman and T. Nyokongiu, in Phthalocyanines, Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH, New York-Weinheim-Cambridge, 1989.
36. E. A. Makarova, V. N. Kopranenkov, V. K. Shevtsov and E. A. Luk'yanets, Chem. Heterocycl. Compd., 1994, 30, 1043.
37. (a) F. D'Sonza, A. Villard, E. Van Caesnelbecke, M. Franzen, T. Boschi, P. Tagliatesta and K. M. Kadish, Inorg. Chem., 1993, 32, 4042
38. (b) K. M. Kadish, Z. Ou, X. Tan, T. Boschi, D. Monti, V. Fares and P. Tagliatesta, J. Chem. Soc., Dalton Trans., 1999, 1595.
39. Handbook of Liquid Crystals, ed. D. Demus, J. Goodby, G. W. Gray, H. W. Spiess and V. Vill, Weinheim, New York, Chichester, Brisbane, Singapore, Toronto; Wiley-VCH, New York, 1998, vol. 2B, ch. XVI, p. 945.
40. B. D. Plate, S. M. Choi, U. Werner-Zwanziger, D. V. Baxter, J. M. Zaleski and M. H. Chisholm, Chem. Mater., 2002, 14, 1930.
41. (a) G Ricciardi, A. Rosa, I. Ciofini and A. Bencini, Inorg. Chem., 1998, 38, 1422
42. (b) G. Ricciardi, A. Bavoso, A. Bencini, A. Rosa, F. Lelj and F. Bonosi, J. Chem. Soc., Dalton Trans., 1996, 13, 2799
43. (c) G. Ricciardi, A. Bencini, A. Bavoso, A. Rosa and F. Lelj, J. Chem. Soc., Dalton Trans., 1996, 15, 3243.
44. Note: Structure (b) has only one chlorine atom in the coordination sphere, whereas the second chlorine atom is at a distance of 3.024 Å from the Pt atom. At the B3LYP/SDD level of approximation, the structures (a) and (b) are nearly isoenergetic, but the use of the polarized 6-31G* basis set leads to a more evident separation in energy. This fact seems to be associated to basis set shortcomings. The lack of polarized basis functions on the negative charged chlorine atoms can induce a basis set superimposition error (BSSE). In the case of structure (b), the BSSE should be larger, because one chlorine atom is part of the external coordination sphere and is close to the methyl groups. This is a quite different spatial arrangement in comparison to structure (a), where the two chlorine atoms are part of the inner coordination sphere and a neutral sulfur atom (S2) is at 3.405 Å from the Pt atom. Structure (c) and structure (d) are square-based pyramidal five-coordinated structures with one chloride donor atom in axial position. As expected for Pt(II) complexes they are energetically by far less accessible in comparison to structure (a).
45. E. M. Maya, E. M. García-Frutos, P. Vázquez, T. Torres, G. Martín, G. Rojo, F. Agulló-López, R. H. González-Jonte, V. R. Ferro, J. M. García de la Vega, I. Ledoux and J. Zyss, J. Phys. Chem. A, 2003, 107, 2110.