1,10-phenanthrolines with tunable luminescence upon protonation: A spectroscopic and computational study

Journal of Physical Chemistry A

Volumn 111, Issue 32, 2007, Pages 7707-7718

  Listorti, Andrea ^b   Degli Esposti, Alessandra ^b   Kishore, Ravuri S K ^a   Kalsani, Venkateshwarlu ^a   Schmittel, Michael ^a   Armaroli, Nicola ^b  

^a UNIVERSITY OF SIEGEN   (Germany)

^b Istituto per la Sintesi Organica e la Fotoreattività   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE SPECTROSCOPY; LUMINESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONATION; QUENCHING; SUBSTITUTION REACTIONS;

ELECTRONIC ABSORPTION; TRIFLUOROACETIC ACID;

AMINES;

PHENANTHROLINE DERIVATIVE; PROTON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; LUMINESCENCE; SPECTROSCOPY;

LUMINESCENCE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENANTHROLINES; PROTONS; SPECTRUM ANALYSIS;

EID: 34548153549     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0723766     Document Type: Article

References (61)

1. deSilva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
2. Bargossi, C.; Fiorini, M. C.; Montalti, M.; Prodi, L.; Zaccheroni, N. Coord. Chem. Rev. 2000, 208, 17.
3. Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3.
4. de Silva, A. P.; Fox, D. B.; Huxley, A. J. M.; Moody, T. S. Coord. Chem. Rev. 2000, 205, 41.
5. Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N. Coord. Chem. Rev. 2000, 205, 59.
6. Fabbrizzi, L.; Licchelli, M.; Rabaioli, G.; Taglietti, A. Coord. Chem. Rev. 2000, 205, 85.
7. Parker, D. Coord. Chem. Rev. 2000, 205, 109.
8. Beer, P. D.; Cadman, J. Coord. Chem. Rev. 2000, 205, 131.
9. Robertson, A.; Shinkai, S. Coord. Chem. Rev. 2000, 205, 157.
10. Keefe, M. H.; Benkstein, K. D.; Hupp, J. T. Coord. Chem. Rev. 2000, 205, 201.
11. Ramamurthy, V.; Schanze, K. S., Eds. Optical sensors and switches; Marcel Dekker: New York, 2001.
12. Prodi, L. New J. Chem. 2005, 29, 20.
13. Callan, J. F.; de Silva, A. P.; Magri, D. C. Tetrahedron 2005, 61, 8551.
14. Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197.
15. Banthia, S.; Samanta, A. J. Phys. Chem. B 2006, 110, 6437.
16. Joshi, H. S.; Jamshidi, R.; Tor, Y. Angew. Chem., Int. Ed. 1999, 38, 2722.
17. Greiner, G.; Maier, I. J. Chem. Soc. Perkin Trans. 2 2002, 1005.
18. Higgins, B.; DeGraff, B. A.; Demas, J. N. Inorg. Chem. 2005, 44, 6662.
19. Wong, K. M. C.; Tang, W. S.; Lu, X. X.; Zhu, N. Y.; Yam, V. W. W. Inorg. Chem. 2005, 44, 1492.
20. Sammes, P. G.; Yahioglu, G. Chem. Soc. Rev. 1994, 23, 327.
21. McMillin, D. R.; McNett, K. M. Chem. Rev. 1998, 98, 1201.
22. Armaroli, N. Chem. Soc. Rev. 2001, 30, 113.
23. Armaroli, N.; De Cola, L.; Balzani, V.; Sauvage, J. P.; DietrichBuchecker, C. O.; Kern, J. M. J. Chem. Soc., Faraday Trans. 1992, 88, 553.
24. Loren, J. C.; Siegel, J. S. Angew. Chem., Int. Ed. 2001, 40, 754.
25. Bencini, A.; Bernardo, M. A.; Bianchi, A.; Fusi, V.; Giorgi, C.; Pina, F.; Valtancoli, B. Eur. J. Inorg. Chem. 1999, 1911.
26. Aragoni, M. C.; Arca, M.; Demartin, F.; Devillanova, F. A.; Isaia, F.; Garau, A.; Lippolis, V.; Jalali, F.; Papke, U.; Shamsipur, M.; Tei, L.; Yari, A.; Verani, G. Inorg. Chem. 2002, 41, 6623.
27. Pina, J.; de Melo, J. S.; Pina, F.; Lodeiro, C.; Lima, J. C.; Parola, A. J.; Soriano, C.; Clares, M. P.; Albelda, M. T.; Aucejo, R.; Garcia-Espana, E. Inorg. Chem. 2005, 44, 7449.
28. Hayashi, K.; Akutsu, H.; Ozaki, H.; Sawai, H. Chem. Commun. 2004, 1386.
29. Armaroli, N. Photochem. Photobiol. Sci. 2003, 2, 73.
30. Armaroli, N.; De Cola, L.; Balzani, V.; Sauvage, J. P.; DietrichBuchecker, C. O.; Kern, J. M.; Bailai, A. J. Chem. Soc., Dalton Trans. 1993, 3241.
31. Brinen, J. S.; Rosebrook, D. D.; Hirt, R. C. J. Phys. Chem. 1963, 67, 2651.
32. Schulman, S. G.; Capomacchia, A. C. J. Phys. Chem. 1975, 79, 1337.
33. Bandyopadhyay, B. N.; Harriman, A. J. Chem. Soc., Faraday Trans. I 1977, 73, 663.
34. Schulman, S. G.; Tidwell, P. T.; Cetorelli, J. J.; Winefordner, J. D. J. Am. Chem. Soc. 1971, 93, 3179.
35. Dietrich-Buchecker, C. O.; Sauvage, J. P.; Armaroli, N.; Ceroni, P.; Balzani, V. New J. Chem. 1996, 20, 801.
36. Armaroli, N.; Ceroni, P.; Balzani, V.; Kern, J. M.; Sauvage, J. P.; Weidmann, J. L. J. Chem. Soc., Faraday Trans. 1997, 93, 4145.
37. Kalsani, V.; Schmittel, M.; Listorti, A.; Accorsi, G.; Armaroli, N. Inorg. Chem. 2006, 45, 2061.
38. Lüning, U.; Müller, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 80.
39. Schmittel, M.; Michel, C.; Wiegrefe, A.; Kalsani, V. Synthesis 2001, 1561.
40. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991.
41. Meech, S. R.; Phillips, D. J. Photochem. 1983, 23, 193.
42. Frisch, M. J.; et al. Gaussian 03, Revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.
43. Hariharan, P. C.; Pople, J. A. Theor. Chem. Ace. 1973, 28, 213.
44. Parr, R. G.; Yang, W. Density-functional theory of atoms and molecules; Oxford University Press: Oxford, UK, 1989.
45. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
46. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
47. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
48. McWeeny, R. In Methods of Molecular Quantum Mechanics; Craig, D. P., McWeeny, R., Eds.; Academic Press: London, UK, 1978.
49. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
50. Dreuw, A.; Weisman, J. L.; Head-Gordon, M. J. Chem. Phys. 2003, 119, 2943.
51. + in the course of the proton addition has been discarded on the basis of lacking high-field shifts of the tert-butyl groups.
52. Dreuw, A.; Head-Gordon, M. Chem. Rev. 2005, 105, 4009.
53. Savin, A.; Umrigar, C. J.; Gonze, X. Chem. Phys. Lett. 1998, 288, 391.
54. Gritsenko, O.; Baerends, E. J. J. Chem. Phys. 2004, 121, 655.
55. Grimme, S.; Parac, M. Chem. Phys. Chem. 2003, 4, 292.
56. Gonzalez-Luque, R.; Serrano-Andres, L.; Merchan, M.; Fulscher, M. P. Theor. Chem. Acc. 2003, 110, 224.
57. Kaim, W. J. Am. Chem. Soc. 1982, 104, 3833.
58. Ernst, S.; Vogler, C.; Klein, A.; Kaim, W.; Zalis, S. Inorg. Chem. 1996, 35, 1295.
59. Farrell, I. R.; Hartl, F.; Zalis, S.; Mahabiersing, T.; Vlcek, A. J. Chem. Soc., Dalton Trans. 2000, 4323.
60. Schaftenaar, G.; Noordik, J. H. J. Comput.-Aided Mol. Des. 2000, 14, 123.
61. Light irradiation of phenanthroline ligands in air-equilibrated dichloromethane solution leads to absorption spectral changes similar to those observed upon protonation, which are also reversible upon addition of base. However, the extensive absorption and emission changes of 8 and 9 in strongly acid environment have been detected also upon removal of oxygen from the solution and working in a dark room. Accordingly we can exclude that the peculiar luminescence behaviour of 8 and 9 in acidic dichloromethane is related to extensive photochemical degradation.