Ferrocenyl-based π-conjugated complexes: Modulation of electronic properties by symmetric/asymmetric cyclopentadienyl substitution

Organometallics

Volumn 24, Issue 6, 2005, Pages 1198-1203

  Paolucci, Demis ^a   Marcaccio, Massimo ^a   Bruno, Carlo ^a   Braga, Dario ^a   Polito, Marco ^a   Paolucci, Francesco ^a   Grepioni, Fabrizia ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; COMPLEXATION; ELECTROCHEMISTRY; ELECTRONIC PROPERTIES; GROUND STATE; MOLECULAR DYNAMICS; ORGANOMETALLICS; OXIDATION; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; REACTION KINETICS; REDOX REACTIONS; SUBSTITUTION REACTIONS; SUPRAMOLECULAR CHEMISTRY;

DENSITY FUNCTIONAL THEORY (DFT); FERROCENYL DIBORONIC ACID; QUANTUM-CHEMICAL METHODS; SUZUKI COUPLING;

TRANSITION METAL COMPOUNDS;

EID: 15944370961     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049212l     Document Type: Article

References (52)

1. (a) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21.
2. (b) Zyss, J.; Ledoux, I.; Volkov, S.; Chernyak, V.; Mukamel, S.; Bartholomew, G. P.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 11956.
3. (c) Lee, J. Y.; Kim, K. S.; Mhin, B. J. J. Chem. Phys. 2001, 115, 9484.
4. (d) Green, M. L.; Marder, S. R.; Thomson, M. E.; Bandy, J. E.; Bloor, D.; Kolinsky, P. V.; Jones, R. J. Nature 1987, 330, 360.
5. (e) Jayaprakash, K. N.; Ray, P. C.; Matsuoka, I.; Bhadbhade, M. M.; Puranik, V. G.; Das, P. K.; Nishihara, H.; Sarkar, A. Organometallics 1999, 18, 3851.
6. (a) Balzani, V.; Juris, A.; Venturi, M.; Campagna, S.; Seroni, S. Chem. Rev. 1996, 96, 759.
7. (b) de Silva, A. P.; McClenaghan, N. D.; McCoy, C. P. Molecular Switches; Wiley-VCH: New York, 2000, pp 339-361.
8. (c) Jiao, J.; Long, G. J.; Grandjean, F.; Beatty, A. M.; Fehlner, T. P. J. Am. Chem. Soc. 2003, 125, 7522.
9. (d) Rambidi, N. G. Microelectron. Eng. 2003, 69, 485.
10. (e) Miyaji, H.; Collinson, S. R.; Prokes, I.; Tucker, J. H. R. Chem. Commun. 2003, 64.
11. (a) de Silva, P. A.; McClenaghan, N. B. Chem. Eur. J. 2004, 10, 574.
12. (b) Credi, A.; Balzani, V.; Langford, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 1997, 119, 2679.
13. (a) Guldi, D. M.; Marcaccio, M.; Paolucci, D.; Paolucci, F.; Tagmatarchis, N.; Tasis, D.; Vázquez, E.; Prato, M. Angew. Chem., Int. Ed. 2003, 42, 4206.
14. (b) Guldi, D. M.; Imahori, H.; Tamaki, K.; Kashiwagi, Y.; Yamada, H.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2004, 108, 541.
15. (c) Campielli, S.; Vàzquez, E.; Milic, D.; Prato, M.; Barberá, J.; Guldi, D. M.; Marcaccio, M.; Paolucci, D.; Paolucci, P.; Deschenaux, R. J. Mater. Chem. 2004, 14, 1266.
16. (d) Carano, M.; Cicogna, F.; D'Ambra, I.; Gaddi, B.; Jngrosso, G.; Mareaccdo, M.; Paolucci, D.; Paolucci, F.; Pinzino, C.; Roffia, S. Organometallica 2002, 21, 5583.
17. (e) Hubig, S. M.; Kochi, J. K. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 618-676, and references cited therein.
18. (a) Braga, D.; Polito, M.; Bracaccini, M.; D'Addario, D.; Tagliavini, E.; Sturba, L.; Grepioni, F. Organometallics 2003, 22, 2142.
19. (b) Braga, D.; Polito, M.; D'Addario, D.; Grepioni, F. Organometallics 2004, 23, 2810.
20. (c) Braga, D.; Polito, M.; D'Addario, D.; Tagliavini, E.; Proserpio, D. M.; Grepioni, F.; Steed, J. W. Organometailics 2003, 22, 4532.
21. Knapp, R.; Rehahn, M. J. Organomet. Chem. 1993, 452, 235.
22. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
23. Marcaccio, M.; Paolucci, F.; Paradisi, C.; Carano, M.; Soffia, S.; Fontanesi, C.; Yellowlees, L. J.; Serroni, S.; Campagna, S.; Balzani, V. J. Electroanal. Chem. 2002, 532, 99.
24. Amatore, C.; Lefrou, C. J. Electroanal. Chem. 1992, 324, 33.
25. Lee, S. M.; Kowallick, R.; Marcaccio, M.; McCleverty, J. A.; Ward, M. D. J. Chem. Soc., Dalton Trans. 1998, 3443.
26. (a) Lever, A. B. P. Inorg. Chem. 1990, 29, 1271.
27. (b) Lu, S.; Streleta, V. V.; Ryan, M. F., Pietro, W. J.; Lever, A. B. P. Inorg. Chem. 1996, 35, 1013.
28. (c) Guedes da Silva, M. F. C.; Trzeciak, A. M.; Zióllcowski, J. J.; Pombeiro, A. J. L. J. Organomet. Chem. 2001, 620, 174.
29. (d) Treichel, P. M.; Durren, G. E.; Mueh, H. J. J. Organomet. Chem. 1972, 44, 339.
30. 13f The calculated gas-phase molecular structures are in excellent agreement with those from X-ray determinations.5
31. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
32. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1873, 28, 213.
33. (c) Rassolov, V.; Pople, J. A.; Ratner, M.; Windus, T. L. J. Chem. Phys. 1998, 109, 1223.
34. (d) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
35. (e) Lee, C.; Wang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
36. (f) Spartan 02; Wavefunction, Inc.
37. Sarapu, A.; Fenske, R. F. Inorg. Chem. 1975, 14, 247.
38. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications; Wiley: New York, 2001; Chapter 12 and pp 200-201.
39. -1. The slow ET kinetics might be associated with the molecular rearrangement coupled to the reduction of the radical monoanion, such as an increase of coplanarity (Figures S2 and S3 in the Supporting Information). Further investigations are currently in progress to identify the nature of such a molecular reorganization.
40. (a) Cattarin, S.; Ceroni, P.; Guldi, D. M.; Maggini, M.; Menna, E.; Paolucci, F.; Roffia, S.; Scorano, G. J. Mater. Chem. 1999, 9, 2743.
41. (b) Zi-Rong, Z.; Evans, D. H. J. Am. Chem. Soc. 1999, 121, 2941.
42. (a) Numes, C. D.; Santoa, T. M.; Carapuça, H. M.; Hazell, A.; Pillinger, M.; Madureire, J.; Xue, W.-M.; Kühn, F. E.; Gonçoives, I. S. New J. Chem. 2002, 26, 1384.
43. (b) Xue, W.-M.; Kühn, F. E.; Herdtweck, E.; Li, Q. Eur. J. Inorg. Chem. 2001, 213.
44. Das, A.; Bajaj, H. C.; Bhadbhade, M. M. J. Organomet. Chem. 1997, 544, 55.
45. Siu-Ming, L.; Marcaccio, M.; McCleverty, J. A.; Ward, M. D. Chem. Mater. 1996, 10, 3272.
46. (a) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629.
47. (b) Carlucci, L.; Ciani, G.; Proserpio, D. M. Cryst. Eng. Commun. 2003, 5, 269.
48. (c) Kitagawa, S.; Kitaura, R.; Noro, S. Angew. Chem., Int. Ed. 2004, 116, 2388.
49. (d) Janiak, C. Dalton 2003, 2781.
50. (a) Haiduc, I.; Edelmann, F. T. Supramolecular Organometallic Chemistry; Wiley-VCH: Weinheim, Germany, 1999.
51. (b) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; Wiley: New York, 2000.
52. (c) Braga, D. Chem. Commun. 2003, 2751.