Integrated NMR and computational study of push-pull NLO probes: Interplay of solvent and structural effects

Journal of Physical Chemistry A

Volumn 115, Issue 35, 2011, Pages 10035-10044

  Marini, Alberto ^a   MacChi, Sara ^a   Jurinovich, Sandro ^a   Catalano, Donata ^a   Mennucci, Benedetta ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BOND LENGTH ALTERNATION; COMPUTATIONAL STUDIES; ELECTRONIC CHARGE DISTRIBUTION; HYPER-POLARIZABILITY; MOLECULAR SYSTEMS; NLO PROPERTIES; NMR MEASUREMENTS; P-NITROANILINE; SOLVENT SENSITIVITY; STRUCTURAL EFFECT;

BOND LENGTH; CHARGE TRANSFER; CHEMICAL ANALYSIS; ION EXCHANGE; SOLVENTS;

NUCLEAR MAGNETIC RESONANCE;

EID: 80052323341     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp203864a     Document Type: Article

References (70)

1. Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: New York, 1991.
2. Chemla, D. S.; Zyss, J. Nonlinear Optical Properties of Organic Molecules and Crystals; Academic Press: New York, 1987.
3. Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1997.
4. Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195
5. Bishop, D. M. Adv. Chem. Phys. 1998, 104, 1
6. Marder, S. R.; Kippelen, B.; Jen, A. K.-Y.; Peyghambarian, N. Nature 1997, 388, 845
7. Marder, S. R.; Cheng, L. T.; Tiemann, B. G.; Friedli, A. C.; Blanchard-Desce, M.; Perry, J. W.; Skindhoej, J. Science 1994, 263, 511
8. Marder, S. R.; Gorman, C. B.; Tiemann, B. G.; Cheng, L. T. J. Am. Chem. Soc. 1993, 115, 2524
9. Marder, S. R.; Beratan, D. N.; Cheng, L.-T. Science 1991, 252, 103
10. Wolff, J. J.; Wortmann, R. Adv. Phys. Org. Chem. 1999, 32, 121
11. Marder, S. R. Chem. Commun. 2006, 131, 131
12. Bossi, A.; Licandro, E.; Maiorana, S.; Rigamonti, C.; Righetto, S.; Stephenson, G. R.; Spassova, M; Botek, E.; Champagne, B. J. Phys. Chem. C 2008, 112, 7900
13. Sergeyev, S.; Didier, D.; Boitsov, V.; Teshome, A.; Asselberghs, I.; Clays, K.; Vande Velde, C. M. L.; Plaquet, A.; Champagne, B. Chem.-Eur. J. 2010, 16, 8181
14. Coe, B. J.; Fielden, J.; Foxon, S. P.; Helliwell, M.; Asselberghs, I.; Clays, K.; De Mey, K.; Brunschwig, B. S. J. Org. Chem. 2010, 75, 8550
15. Abbotto, A.; Beverina, L.; Bradamante, S.; Facchetti, A.; Klein, C.; Pagani, G. A.; Abshiro, M. R.; Wortmann, R. D. Chem.-Eur. J. 2003, 9, 1991
16. Archetti, G; Abbotto, A.; Wortmann, R. D. Chem.-Eur. J. 2006, 12, 7151
17. Bogdan, E.; Plaquet, A.; Antonov, L.; Rodriguez, V.; Ducasse, L.; Champagne, B.; Castet, F. J. Phys. Chem. C 2010, 114, 12760
18. Willetts, A.; Rice, J. E. J. Chem. Phys. 1993, 99, 426
19. Yu, J.; Zerner, M. C. J. Chem. Phys. 1994, 100, 7487
20. Sylvester-Hvid, K. O.; Mikkelsen, K. V.; Jonsson, D.; Norman, P.; Å gren, H. J. Chem. Phys. 1998, 5576, 109
21. Kongsted, J.; Osted, A.; Mikkelsen, K. V.; Christiansen, O. J. Chem. Phys. 2003, 119, 10519
22. Sylvester-Hvid; Mikkelsen; Norman; Jonsson; Ågren J. Phys. Chem. A 2004, 108, 8961
23. Cammi, R.; Cossi, M.; Mennucci, B.; Tomasi J. Chem. Phys. 1996, 105, 10556
24. Cammi, R.; Mennucci, B.; Tomasi, J. J. Am. Chem. Soc. 1998, 120, 8834
25. Mennucci, B.; Cammi, R.; Tomasi, J. Int. J. Quantum Chem. 1999, 75, 767
26. Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 4690
27. Corozzi, A.; Mennucci, B.; Cammi, R.; Tomasi, J. J. Phys. Chem. A 2009, 113, 14774
28. Munn, R. W.; Luo, Y.; Macak, P.; Å gren, H. J. Chem. Phys. 2001, 114, 3105
29. Ray, P. C.; Leszcynski, J. Chem. Phys. Lett. 2004, 399, 162
30. Frediani, L.; Å gren, H.; Ferrighi, L.; Ruud, K. J. Chem. Phys. 2005, 123, 144117
31. Ferrighi, L.; Frediani, L.; Cappelli, C.; Salek, P.; Å gren, H.; Helgaker, T.; Ruud, K. Chem. Phys. Lett. 2006, 425, 267
32. Jensen, L.; van Duijnen, P. T.; Snijders, J. G. J. Chem. Phys. 2003, 119, 12998
33. Jensen, L.; van Duijnen, P. T. J. Chem. Phys. 2005, 123, 074307
34. Matichak, J. D.; Hales, J. M.; Barlow, S.; Perry, J. W.; Marder, S. R. J. Phys. Chem. A 2011, 115, 2160
35. Molinos-Gomez, A.; Vidal, X.; Maymo, M.; Velasco, D.; Martorell, J.; Lopez-Calahorra, F. Tetrahedron 2005, 61, 9075
36. Kleinpeter, E.; Koch, A.; Mikhova, B.; Stamboliyska, B. A.; Kolev, T. M. Tetrahedron Lett. 2008, 49, 1323
37. Kleinpeter, E.; Klod, S.; Rudorf, W.-D. J. Org. Chem. 2004, 69, 4317
38. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
39. In Continuum solvation models in chemical physics, from theory to applications; Mennucci, B.; Cammi, R., Eds.; Wiley: Chichester, 2007.
40. Bohmann, J. A.; Weinhold, F.; Farrar, T. C. J. Chem. Phys. 1997, 107, 1173
41. Frisch, M. J. Gaussian 09,Revision A01; Gaussian, Inc.: Wallingford, CT, 2009.
42. Becke, A. D. Phys. Rev. A 1988, 38, 3098
43. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785
44. Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393, 51
45. Chiba, M.; Tsuneda, T.; Hirao, K. J. Chem. Phys. 2006, 124, 144106
46. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158
47. Ernzerhof, M.; Scuseria, G. E. J. Chem. Phys. 1999, 110, 5029
48. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664
49. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101
50. Kupka, T.; Stachow, M.; Nieradka, M.; Kaminsky, J.; Pluta, T. J. Chem. Theory Comput. 2010, 6, 1580
51. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. Lett. 2008, 112, 6794
52. Hameka, H. F. Rev. Mod. Phys. 1962, 34, 87
53. Ditchfield, R. Mol. Phys. 1974, 27, 789
54. Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251
55. Cancès, E.; Mennucci, B. J. Math. Chem. 1998, 23, 309
56. Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032
57. Mennucci, B.; Cancès, E.; Tomasi, J. J. Phys. Chem. B 1997, 101, 10506
58. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024
59. Willetts, A.; Rice, J. E.; Burland, D. M.; Shelton, D. P. J. Chem. Phys. 1992, 97, 7590
60. Shi, R. F.; Garito, A. F. In Characterization Techniques and Tabulations for Organic Nonlinear Optical Materials; Kuzyk, M. G.; Dirk, C. W., Eds.; Dekker: New York, 1998; p 128.
61. Reis, H. J. Chem. Phys. 2006, 125, 014506
62. Ferrighi, L.; Frediani, L.; Cappelli, C.; Sałek, P.; Ågren, H.; Helgaker, T.; Ruud, K. Chem. Phys. Lett. 2006, 425, 267
63. Peach, M. J. G.; Helgaker, T.; Sałek, P.; Keal, T. W.; Lutnaes, O. B.; Tozer, D. J.; Handy, N. C. Phys. Chem. Chem. Phys. 2006, 8, 558
64. Jacquemin, D.; Perpete, E. A.; Scalmani, G.; Frisch, M. J.; Kobayashi, R.; Adamo, C. J. Chem. Phys. 2007, 126, 144105
65. Jacquemin, D.; Perpete, E; Medved, M.; Scalmani, G.; Frisch, M. J.; Kobayashi, R.; Adamo, C. J. Chem. Phys. 2007, 126, 191108
66. Helgaker, T.; Jaszunski, M.; Ruud, K. Chem. Rev. 1999, 99, 293
67. Calculation of NMR and EPR Parameters. Theory and Applications; Kaupp, M.; Buhl, M.; Malkin, V. G., Eds.; Wiley-VCH: Weinheim, 2004.
68. Kupka, T.; Stachow, M.; Nieradka, M.; Kaminsky, J.; Pluta, T. J. Chem. Theory Comput. 2010, 6, 1580
69. Deng, W.; Cheeseman, J. R.; Frisch, M. J. J. Chem. Theory Comput. 2006, 2, 1028
70. Jensen, F. J. Chem. Theory Comput. 2006, 2, 1360