Tictoid expanded pyridiniums: Assessing structural, electrochemical, electronic, and photophysical features

Journal of Physical Chemistry A

Volumn 116, Issue 30, 2012, Pages 7880-7891

  Fortage, Jérôme ^a   Tuyèras, Fabien ^a   Peltier, Cyril ^b   Dupeyre, Grégory ^a   Calboréan, Adrian ^b,c   Bedioui, Fethi ^a   Ochsenbein, Philippe ^e   Puntoriero, Fausto ^d   Campagna, Sebastiano ^d   Ciofini, Ilaria ^b   Lainé, Philippe P ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b PSL RESEARCH UNIVERSITY   (France)

^c NATIONAL INSTITUTE FOR RESEARCH AND DEVELOPMENT OF ISOTOPIC AND MOLECULAR TECHNOLOGIES   (Romania)

^d UNIVERSITY OF MESSINA   (Italy)

^e SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACCEPTOR MOIETIES; BULKY SUBSTITUENTS; CHARGE RECOMBINATIONS; COMPENSATION EFFECTS; DONOR SPACER ACCEPTORS; ELECTRON-DONATING; ELECTRONIC INFLUENCE; ELECTRONWITHDRAWING; HIGH ENERGY; HOMO ENERGIES; PHOTOINDUCED CHARGE SEPARATION; PHOTOPHYSICAL; PHOTOPHYSICAL PROPERTIES; TWIST ANGLES;

PHYSICAL CHEMISTRY; PHYSICS;

ELECTRONIC STRUCTURE;

PYRIDINIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; ELECTRON; PHOTOCHEMISTRY; QUANTUM THEORY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMICAL TECHNIQUES; ELECTRONS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; PYRIDINIUM COMPOUNDS; QUANTUM THEORY;

EID: 84864773095     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp3043158     Document Type: Article

References (52)

1. Ceroni, P.; Credi, A.; Venturi, M.; Balzani, V. Photochem. Photobiol. Sci. 2010, 9, 1561-1573
2. Balzani, V.; Credi, A.; Venturi, M. ChemSusChem 2008, 1, 26-58
3. Lainé, P. P.; Campagna, S.; Loiseau, F. Coord. Chem. Rev. 2008, 252, 2552-2571
4. Lainé, P. P.; Ciofini, I.; Ochsenbein, P.; Amouyal, E.; Adamo, C.; Bedioui, F. Chem.-Eur. J. 2005, 11, 3711-3727
5. Ciofini, I.; Adamo, C.; Teki, Y.; Tuyèras, F.; Lainé, P. P. Chem.-Eur. J. 2008, 14, 11385-11405
6. De Cola, L.; Belser, P.; Von Zelewsky, A.; Vögtle, F. Inorg. Chim. Acta 2007, 360, 775-784
7. Lainé, P.; Bedioui, F.; Ochsenbein, P.; Marvaud, V.; Bonin, M.; Amouyal, E. J. Am. Chem. Soc. 2002, 124, 1364-1377
8. Lainé, P.; Bedioui, F.; Amouyal, E.; Albin, V.; Berruyer-Penaud, F. Chem.-Eur. J. 2002, 8, 3162-3176
9. Lainé, P.; Amouyal, E. Chem. Commun. 1999, 935-936
10. Lainé, P. P.; Bedioui, F.; Loiseau, F.; Chiorboli, C.; Campagna, S. J. Am. Chem. Soc. 2006, 128, 7510-7521
11. Lainé, P. P.; Loiseau, F.; Campagna, S.; Ciofini, I.; Adamo, C. Inorg. Chem. 2006, 45, 5538-5551
12. Ciofini, I.; Lainé, P. P.; Bedioui, F.; Adamo, C. J. Am. Chem. Soc. 2004, 126, 10763-10777
13. Meylemans, H. A.; Damrauer, N. H. Inorg. Chem. 2009, 48, 11161-11175
14. Hanss, D.; Wenger, O. S. Eur. J. Inorg. Chem. 2009, 3778-3790
15. Indelli, M. T.; Chiorboli, C.; Flamigni, L.; De Cola, L.; Scandola, F. Inorg. Chem. 2007, 46, 5630-5641
16. Benniston, A. C.; Harriman, A.; Li, P.; Patel, P. V.; Sams, C. A. J. Org. Chem. 2006, 71, 3481-3493
17. Benniston, A. C.; Harriman, A. Chem. Soc. Rev. 2006, 35, 169-179
18. Kang, H.; Facchetti, A.; Zhu, P.; Jiang, H.; Yang, Y.; Cariati, E.; Righetto, S.; Ugo, R.; Zuccaccia, C.; Macchioni, A.; Stern, C. L.; Liu, Z.; Ho, S.-T.; Marks, T. J. Angew. Chem., Int. Ed. 2005, 44, 7922-7925
19. Albert, I. D. L.; Marks, T. J.; Ratner, M. A. J. Am. Chem. Soc. 1998, 120, 11174-11181
20. Walther, M. E.; Wenger, O. S. ChemPhysChem 2009, 10, 1203-1206
21. Fortage, J.; Tuyèras, F.; Ochsenbein, P.; Puntoriero, F.; Nastasi, F.; Campagna, S.; Griveau, S.; Bedioui, F.; Ciofini, I.; Lainé, P. P. Chem.-Eur. J. 2010, 16, 11047-11063
22. Peltier, C.; Adamo, C.; Lainé, P. P.; Campagna, S.; Puntoriero, F.; Ciofini, I. J. Phys. Chem. A 2010, 114, 8434-8443
23. Fortage, J.; Peltier, C.; Nastasi, F.; Puntoriero, F.; Tuyèras, F.; Griveau, S.; Bedioui, F.; Adamo, C.; Ciofini, I.; Campagna, S.; Lainé, P. P. J. Am. Chem. Soc. 2010, 132, 16700-16713
24. Fortage, J.; Peltier, C.; Perruchot, C.; Takemoto, Y.; Teki, Y.; Bedioui, F.; Marvaud, V.; Dupeyre, G.; Pospisil, L.; Adamo, C.; Hromadova, M.; Ciofini, I.; Lainé, P. P. J. Am. Chem. Soc. 2012, 134, 2691-2705
25. Ziegler, T Chem. Rev. 1991, 91, 651-667
26. Cramer, C. J.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2009, 11, 10757-10816
27. Burke, K; Werschnik, J; Gross, E. K. U. J. Chem. Phys. 2005, 123, 062206-2
28. Jacquemin, D.; Perpète, E. A.; Ciofini, I.; Adamo, C. Acc. Chem. Res. 2009, 42, 326-334
29. Improta, R. In Computational Strategies for Spectroscopy: From Small Molecules to NanoSystems; Barone, V., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2011; pp 39-77.
30. Le Bahers, T.; Pauporté, T.; Scalmani, G.; Adamo, C.; Ciofini, I. Phys. Chem. Chem. Phys. 2009, 11, 11276-11284
31. Le Bahers, T.; Pauporté, T.; Labat, F.; Lainé, P. P.; Ciofini, I. J. Am. Chem. Soc. 2011, 133, 8005-8013
32. Rekhis, M.; Labat, F.; Ouamerali, O.; Ciofini, I.; Adamo, C. J. Phys. Chem. A 2008, 111, 13106-13111
33. Di Pietro, M. L.; Puntoriero, F.; Tuyèras, F.; Ochsenbein, P.; Lainé, P. P.; Campagna, S. Chem. Commun. 2010, 46, 5169-5171
34. Katritzky, A. R.; Zakaria, Z.; Lunt, E.; Jones, P. G.; Kennard, O. J. Chem. Soc., Chem. Commun. 1979, 268-269
35. Katritzky, A. R.; Zakaria, Z.; Lunt, E. J. Chem. Soc., Perkin Trans. 1 1980, 1879-1887
36. Kharlanov, V. A.; Knyazhansky, M. I. J. Photochem. Photobiol. A 1999, 125, 21-27
37. Knyazhansky, M. I.; Kharlanov, V. A.; Tymiansky, Ya. R. J. Photochem. Photobiol. A 1998, 118, 151-156
38. Knyazhanskii, M. I.; Tymyanskii, Y. R.; Feigelman, V. M.; Katritzky, A. R. Heterocycles 1987, 26, 2963-2982
39. Peltier, C.; Lainé, P. P.; Scalmani, G.; Frisch, M. J.; Adamo, C.; Ciofini, I. J. Mol. Struct.: THEOCHEM 2009, 914, 94-99
40. Fortage, J.; Puntoriero, F.; Tuyèras, F.; Dupeyre, G.; Arrigo, A.; Ciofini, I.; Lainé, P. P.; Campagna, S. Inorg. Chem. 2012, 51, 5342-5352
41. Indelli, M. T.; Orlandi, M.; Chiorboli, C.; Ravaglia, M.; Scandola, F.; Lafolet, F.; Welter, S.; De Cola, L. J. Phys. Chem. A 2012, 116, 119-131
42. Weiss, E. A.; Ahrens, M. J.; Sinks, L. E.; Gusev, A. V.; Ratner, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 5577-5584
43. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology; Carter, C. W.; Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276 (Macromolecular Crystallography, Part A), pp 307-326.
44. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122
45. Pavlishchuk, V. V.; Addison, A. W. Inorg. Chim. Acta 2000, 298, 97-102
46. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991-1024
47. Dempster, D. N.; Morrow, T.; Quinn, M. F. J. Photochem. 1974, 2, 329-341
48. Frisch, M. J; Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
49. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158-6170
50. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, pp 1-28.
51. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
52. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G.; Guido, C. A.; Mennucci, B.; Scalmani, G.; Frisch, M. J. Chem. Sci. 2011, 2, 2143-2161