Quadratic and cubic nonlinear optical properties of salts of diquat-based chromophores with diphenylamino substituents

Journal of Physical Chemistry A

Volumn 114, Issue 45, 2010, Pages 12028-12041

  Coe, Benjamin J ^a   Fielden, John ^a   Foxon, Simon P ^a   Helliwell, Madeleine ^a   Brunschwig, Bruce S ^b   Asselberghs, Inge ^c   Clays, Koen ^c   Olesiak, Joanna ^d   Matczyszyn, Katarzyna ^d   Samoc, Marek ^d,e  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^c UNIVERSITY OF LEUVEN   (Belgium)

^d WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^e AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2D STRUCTURES; BIPYRIDYL; CENTROSYMMETRIC; CINNAMALDEHYDE; ELECTRO-ABSORPTION; ELECTRON DONORS; ELECTRON-ACCEPTING; ELECTRON-ACCEPTOR; ELECTRONIC ABSORPTION SPECTROSCOPY; FIRST HYPERPOLARIZABILITIES; HYPER RAYLEIGH SCATTERING; INTRAMOLECULAR CHARGE TRANSFERS; NLO PROPERTIES; NON-LINEAR OPTICAL PROPERTIES; NONLINEAR OPTICAL EFFECTS; PRECURSOR COMPOUNDS; SINGLE CRYSTAL X-RAY STRUCTURES; SPACE GROUPS; SWITCHABLE; TWO-PHOTON ABSORPTIONS; VISIBLE ABSORPTION SPECTRA; WAVELENGTH RANGES; Z-SCAN TECHNIQUE;

ABSORPTION; ALDEHYDES; CARBONYLATION; CHARGE TRANSFER; CHROMOPHORES; CYCLIC VOLTAMMETRY; ELECTRON ENERGY LOSS SPECTROSCOPY; LIGHT ABSORPTION; NONLINEAR OPTICS; OPTICAL PROPERTIES; SALTS; SINGLE CRYSTALS; TWO PHOTON PROCESSES;

ABSORPTION SPECTROSCOPY;

EID: 78449268124     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp106473e     Document Type: Article

References (169)

1. Séliwa, W.; Matusiak, G.; Bachowska, B. Croat. Chem. Acta 2006, 79, 513
2. Yuan, C.-X.; Tao, X.-T.; Ren, Y.; Li, Y.; Yang, J.-X.; Yu, W.-T.; Wang, L.; Jiang, M.-H. J. Phys. Chem. C 2007, 111, 12811
3. Yuan, C.-X.; Tao, X.-T.; Wang, L.; Yang, J.-X.; Jiang, M.-H. J. Phys. Chem. C 2009, 113, 6809
4. Kim, H. S.; Pham, T. T.; Yoon, K. B. J. Am. Chem. Soc. 2008, 130, 2134
5. Han, Z.-F.; Vaid, T. P.; Rheingold, A. L. J. Org. Chem. 2008, 73, 445
6. Xu, G.; Li, Y.; Zhou, W.-W.; Wang, G.-J.; Long, X.-F.; Cai, L.-Z.; Wang, M.-S.; Guo, G.-C.; Huang, J.-S.; Bator, G.; Jakubas, R. J. Mater. Chem. 2009, 19, 2179
7. Feng, S.-H.; Kim, Y. K.; Yang, S.-Q.; Chang, Y.-T. Chem. Commun. 2010, 46, 436
8. Selected general reviews
9. Molecular Nonlinear Optics: Materials, Physics and Devices; Zyss, J.; Academic Press: Boston, 1994.
10. Organic Nonlinear Optical Materials; Bosshard, Ch.; Sutter, K.; Prětre, Ph.; Hulliger, J.; Floärsheimer, M.; Kaatz, P.; Guänter, P. Eds.; Advances in Nonlinear Optics, Vol. 1; Gordon & Breach: Amsterdam, The Netherlands, 1995.
11. Nonlinear Optics of Organic Molecules and Polymers; Nalwa, H. S.; Miyata, S., Eds.; CRC Press: Boca Raton, FL, 1997.
12. Marder, S. R. Chem. Commun. 2006, 131
13. Nonlinear Optical Properties of Matter: From Molecules to Condensed Phases; Papadopoulos, M. G.; Leszczynski, J.; Sadlej, A. J., Eds.; Springer: Dordrecht, 2006.
14. Kuzyk, M. G. J. Mater. Chem. 2009, 19, 7444
15. Selected examples
16. Marder, S. R.; Perry, J. W.; Schaefer, W. P. Science 1989, 245, 626
17. Marder, S. R.; Perry, J. W.; Schaefer, W. P. J. Mater. Chem. 1992, 2, 985
18. Marder, S. R.; Perry, J. W.; Yakymyshyn, C. P. Chem. Mater. 1994, 6, 1137
19. Lee, O.-K.; Kim, K.-S. Photonics Sci. News 1999, 4, 9
20. Sohma, S.; Takahashi, H.; Taniuchi, T.; Ito, H. Chem. Phys. 1999, 245, 359
21. Kaino, T.; Cai, B.; Takayama, K. Adv. Funct. Mater. 2002, 12, 599
22. Mohan Kumar, R.; Rajan Babu, D.; Ravi, G.; Jayavel, R. J. Cryst. Growth 2003, 250, 113
23. Geis, W.; Sinta, R.; Mowers, W.; Deneault, S. J.; Marchant, M. F.; Krohn, K. E.; Spector, S. J.; Calawa, D. R.; Lyszczarz, T. M. Appl. Phys. Lett. 2004, 84, 3729
24. Kuroyanagi, K.; Yanagi, K.; Sugita, A.; Hashimoto, H.; Takahashi, H.; Aoshima, S.-i.; Tsuchiya, Y. J. Appl. Phys. 2006, 100 043117
25. Liu, J.-J.; Merkt, F. Appl. Phys. Lett. 2008, 93, 131105
26. Macchi, R.; Cariati, E.; Marinotto, D.; Roberto, D.; Tordin, E.; Ugo, R.; Bozio, R.; Cozzuol, M.; Pedron, D.; Mattei, G. J. Mater. Chem. 2010, 20, 1885
27. Selected examples
28. Yitzchaik, S.; Marks, T. J. Acc. Chem. Res. 1996, 29, 197
29. Alain, V.; Blanchard-Desce, M.; Ledoux-Rak, I.; Zyss, J. Chem. Commun. 2000, 353
30. Cariati, E.; Ugo, R.; Cariati, F.; Roberto, D.; Masciocchi, N.; Galli, S.; Sironi, A. Adv. Mater. 2001, 13, 1665
31. Abbotto, A.; Beverina, L.; Bradamante, S.; Facchetti, A.; Klein, C.; Pagani, G. A.; Redi-Abshiro, M.; Wortmann, R. Chem. - Eur. J. 2003, 9, 1991
32. Kim, H. S.; Lee, S. M.; Ha, K.; Jung, C.; Lee, Y.-J.; Chun, Y. S.; Kim, D.; Rhee, B. K.; Yoon, K. B. J. Am. Chem. Soc. 2004, 126, 673
33. Yang, Z.; Aravazhi, S.; Schneider, A.; Seiler, P.; Jazbinšek, M.; Guänter, P. Adv. Funct. Mater. 2005, 15, 1072
34. Ruiz, B.; Yang, Z.; Gramlich, V.; Jazbinšek, M.; Guänter, P. J. Mater. Chem. 2006, 16, 2839
35. Kim, H. S.; Sohn, K. W.; Jeon, Y.; Min, H.; Kim, D.; Yoon, K. B. Adv. Mater. 2007, 19, 260
36. Yang, Z.; Jazbinšek, M.; Ruiz, B.; Aravazhi, S.; Gramlich, V.; Guänter, P. Chem. Mater. 2007, 19, 3512
37. Morotti, T.; Calabrese, V.; Cavazzini, M.; Pedron, D.; Cozzuol, M.; Licciardello, A.; Tuccitto, N.; Quici, S. Dalton Trans. 2008, 2974
38. Figi, H.; Mutter, L.; Hunziker, C.; Jazbinšek, M.; Guänter, P.; Coe, B. J. J. Opt. Soc. Am. B 2008, 25, 1786
39. Compain, J.-D.; Mialane, P.; Dolbecq, A.; Marrot, J.; Proust, A.; Nakatani, K.; Yu, P.; Seécheresse, F. Inorg. Chem. 2009, 48, 6222
40. Selected examples
41. Kawase, K.; Mizuno, M.; Sohma, S.; Takahashi, H.; Taniuchi, T.; Urata, Y.; Wada, S.; Tashiro, H.; Ito, H. Opt. Lett. 1999, 24, 1065
42. Kawase, K.; Hatanaka, T.; Takahashi, H.; Nakamura, K.; Taniuchi, T.; Ito, H. Opt. Lett. 2000, 25, 1714
43. Taniuchi, T.; Okada, S.; Nakanishi, H. Appl. Phys. Lett. 2004, 95, 5984
44. Taniuchi, T.; Ikeda, S.; Okada, S.; Nakanishi, H. Jap. J. Appl. Phys. 2005, 44, L652
45. Schneider, A.; Neis, M.; Stillhart, M.; Ruiz, B.; Khan, R. U. A.; Guänter, P. J. Opt. Soc. Am. B 2006, 23, 1822
46. Schneider, A.; Stillhart, M.; Guänter, P. Opt. Express 2006, 14, 5376
47. Yang, Z.; Mutter, L.; Stillhart, M.; Ruiz, B.; Aravazhi, S.; Jazbinšek, M.; Schneider, A.; Gramlich, V.; Guänter, P. Adv. Funct. Mater. 2007, 17, 2018
48. Terahertz Sources and Systems; Miles, R. E.; Harrison, P.; Lippens, D., Eds.; NATO Science Series II,; Kluwer: Dordrecht, 2001; Vol. 27.
49. Ferguson, B.; Zhang, X.-C. Nat. Mater. 2002, 1, 26
50. McEntee, J. Chem. World 2007, March, 52-56
51. http://www.teraview.com, TeraView terahertz technology for 3D imaging and spectroscopy, accessed October 14, 2010.
52. Selected examples
53. Wang, C.; Wang, X.-M.; Shao, Z.-S.; Zhao, X.; Zhou, G.-Y.; Wang, D.; Fang, Q.; Jiang, M.-H. Appl. Opt. 2001, 40, 2475
54. Zheng, Q.-D.; He, G. S.; Lin, T.-C.; Prasad, P. N. J. Mater. Chem. 2003, 13, 2499
55. He, G. S.; Lin, T.-C.; Prasad, P. N.; Cho, C.-C.; Yu, L.-J. Appl. Phys. Lett. 2003, 82, 4717
56. Yang, Z.; Wu, Z.-K.; Ma, J.-S.; Xia, A.-D.; Li, Q.-S.; Liu, C.-L.; Gong, Q.-H. Appl. Phys. Lett. 2005, 86 061903
57. Samoc, M.; Morrall, J. P.; Dalton, G. T.; Cifuentes, M. P.; Humphrey, M. G. Angew. Chem., Int. Ed. 2007, 46, 731
58. Terenziani, F.; Katan, C.; Badaeva, E.; Tretiak, S.; Blanchard-Desce, M. Adv. Mater. 2008, 20, 4641
59. Jana, A.; Jang, S. Y.; Shin, J.-Y.; De, A. K.; Goswami, D.; Kim, D.; Bharadwaj, P. J. Chem. - Eur. J. 2008, 14, 10628
60. D'Aleéo, A.; Picot, A.; Baldeck, P. L.; Andraud, C.; Maury, O. Inorg. Chem. 2008, 47, 10269
61. He, G. S.; Tan, L.-S.; Zheng, Q.-D.; Prasad, P. N. Chem. Rev. 2008, 108, 1245
62. Collings, J. C.; Poon, S.-Y.; Le Droumaguet, C.; Charlot, M.; Katan, C.; Pålsson, L.-O.; Beeby, A.; Mosely, J. A.; Kaiser, H. M.; Kaufmann, D.; Wong, W.-Y.; Blanchard-Desce, M.; Marder, T. B. Chem. - Eur. J. 2009, 15, 198
63. Pawlicki, M.; Collins, H. A.; Denning, R. G.; Anderson, H. L. Angew. Chem., Int. Ed. 2009, 48, 3244
64. Dvornikov, A. S.; Walker, E. P.; Rentzepis, P. M. J. Phys. Chem. A 2009, 113, 13633
65. Selected examples
66. Wortmann, R.; Kraämer, P.; Glania, C.; Lebus, S.; Detzer, N. Chem. Phys. 1993, 173, 99
67. Moylan, C. R.; Ermer, S.; Lovejoy, S. M.; McComb, I.-H.; Leung, D. S.; Wortmann, R.; Kraämer, P.; Twieg, R. J. J. Am. Chem. Soc. 1996, 118, 12950
68. Di Bella, S.; Fragalà, I.; Ledoux, I.; Diaz-Garcia, M. A.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 9550
69. Wolff, J. J.; Laängle, D.; Hillenbrand, D.; Wortmann, R.; Matschiner, R.; Glania, C.; Kraämer, P. Adv. Mater. 1997, 9, 138
70. Averseng, F.; Lacroix, P. G.; Malfant, I.; Lenoble, G.; Cassoux, P.; Nakatani, K.; Maltey-Fanton, I.; Delaire, J. A.; Aukauloo, A. Chem. Mater. 1999, 11, 995
71. Hilton, A.; Renouard, T.; Maury, O.; Le Bozec, H.; Ledoux, I.; Zyss, J. Chem. Commun. 1999, 2521
72. Lacroix, P. G. Eur. J. Inorg. Chem. 2001, 339
73. Ostroverkhov, V.; Petschek, R. G.; Singer, K. D.; Twieg, R. J. Chem. Phys. Lett. 2001, 340, 109
74. Di Bella, S.; Fragalà, I.; Ledoux, I.; Zyss, J. Chem. - Eur. J. 2001, 7, 3738
75. Yang, M.-L.; Champagne, B. J. Phys. Chem. A 2003, 107, 3942
76. Wortmann, R.; Lebus-Henn, S.; Reis, H.; Papadopoulos, M. G. J. Mol. Struct. (Theochem) 2003, 633, 217
77. Cui, Y.-Z.; Fang, Q.; Huang, Z.-L.; Xue, G.; Yu, W.-T.; Lei, H. Opt. Mater. 2005, 27, 1571
78. Rigamonti, L.; Demartin, F.; Forni, A.; Righetto, S.; Pasini, A. Inorg. Chem. 2006, 45, 10976
79. Li, H.-P.; Han, K.; Tang, G.; Shen, X.-P.; Wang, H.-T.; Huang, Z.-M.; Zhang, Z.-H.; Bai, L.; Wang, Z.-Y. Chem. Phys. Lett. 2007, 444, 80
80. Zrig, S.; Koeckelberghs, G.; Verbiest, T.; Andrioletti, B.; Rose, E.; Persoons, A.; Asselberghs, I.; Clays, K. J. Org. Chem. 2007, 72, 5855
81. Liu, C.-G.; Qiu, Y.-Q.; Su, Z.-M.; Yang, G.-C.; Sun, S.-L. J. Phys. Chem. C 2008, 112, 7021
82. Selected examples
83. Verbiest, T.; Clays, K.; Samyn, C.; Wolff, J.; Reinhoudt, D.; Persoons, A. J. Am. Chem. Soc. 1994, 116, 9320
84. Zyss, J.; Ledoux, I. Chem. Rev. 1994, 94, 77
85. Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339
86. McDonagh, A. M.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B.; Houbrechts, S.; Wada, T.; Sasabe, H.; Persoons, A. J. Am. Chem. Soc. 1999, 121, 1405
87. Vance, F. W.; Hupp, J. T. J. Am. Chem. Soc. 1999, 121, 4047
88. Wolff, J. J.; Siegler, F.; Matschiner, R.; Wortmann, R. Angew. Chem., Int. Ed. 2000, 39, 1436
89. Cho, B. R.; Piao, M. J.; Son, K. H.; Lee, S. H.; Yoon, S. J.; Jeon, S.-J.; Cho, M.-H. Chem. - Eur. J. 2002, 8, 3907
90. Le Bouder, T.; Maury, O.; Bondon, O.; Costuas, K.; Amouyal, E.; Ledoux, I.; Zyss, J.; Le Bozec, H. J. Am. Chem. Soc. 2003, 125, 12284
91. Maury, O.; Viau, L.; Seéneéchal, K.; Corre, B.; Gueégan, J.-P.; Renouard, T.; Ledoux, I.; Zyss, J.; Le Bozec, H. Chem. - Eur. J. 2004, 10, 4454
92. Maury, O.; Le Bozec, H. Acc. Chem. Res. 2005, 38, 691
93. Coe, B. J.; Harris, J. A.; Brunschwig, B. S.; Asselberghs, I.; Clays, K.; Garién, J.; Orduna, J. J. Am. Chem. Soc. 2005, 127, 13399
94. Le Floc'h, V.; Brasselet, S.; Zyss, J.; Cho, B. R.; Lee, S. H.; Jeon, S.-J.; Cho, M.-H.; Min, K. S.; Suh, M. P. Adv. Mater. 2005, 17, 196
95. Hennrich, G.; Omenat, A.; Asselberghs, I.; Foerier, S.; Clays, K.; Verbiest, T.; Serrano, J. L. Angew. Chem., Int. Ed. 2006, 45, 4203
96. Jeong, M.-Y.; Kim, H. M.; Jeon, S.-J.; Brasselet, S.; Cho, B. R. Adv. Mater. 2007, 19, 2107
97. Liu, Y.; Xu, X.; Zheng, F.; Cui, Y. Angew. Chem., Int. Ed. 2008, 47, 4538
98. Akdas-Kilig, H.; Roisnel, T.; Ledoux, I.; Le Bozec, H. New J. Chem. 2009, 33, 1470
99. Coe, B. J.; Harris, J. A.; Brunschwig, B. S.; Garién, J.; Orduna, J. J. Am. Chem. Soc. 2005, 127, 3284
100. Coe, B. J.; Fielden, J.; Foxon, S. P.; Harris, J. A.; Helliwell, M.; Brunschwig, B. S.; Asselberghs, I.; Clays, K.; Garién, J.; Orduna, J. J. Am. Chem. Soc. 2010, 132, 10498
101. Zhou, Y.-F.; Meng, F.-Q.; Zhao, X.; Feng, S.-Y.; Jiang, M.-H. Chem. Phys. 2001, 269, 441
102. Hartshorn, C. M.; Maxwell, K. A.; White, P. S.; DeSimone, J. M.; Meyer, T. J. Inorg. Chem. 2001, 40, 601
103. Gillaizeau-Gauthier, I.; Odobel, F.; Alebbi, M.; Argazzi, R.; Costa, E.; Bignozzi, C. A.; Qu, P.; Meyer, G. J. Inorg. Chem. 2001, 40, 6073
104. Lindner, E.; von Au, G.; Eberle, H.-J. Chem. Ber. 1981, 114, 810
105. CrysAlis RED, Version 1.171.32.29; Oxford Diffraction Ltd., Yarnton: Oxfordshire, United Kingdom, 2006.
106. SAINT, Version 6.45; Bruker AXS Inc.: Madison, Wisconsin, USA, 2003.
107. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435
108. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837
109. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467
110. Sheldrick, G. M. SHELXS 97: Programs for Crystal Structure Analysis, Release 97 - 2; University of Goättingen: Goättingen, Germany, 1997.
111. SHELXTL, Version 6.10; Bruker AXS Inc.: Madison, Wisconsin, USA, 2000.
112. Clays, K.; Persoons, A. Phys. Rev. Lett. 1991, 66, 2980
113. Clays, K.; Persoons, A. Rev. Sci. Instrum. 1992, 63, 3285
114. Hendrickx, E.; Clays, K.; Persoons, A. Acc. Chem. Res. 1998, 31, 675
115. Olbrechts, G.; Strobbe, R.; Clays, K.; Persoons, A. Rev. Sci. Instrum. 1998, 69, 2233
116. Olbrechts, G.; Wostyn, K.; Clays, K.; Persoons, A. Opt. Lett. 1999, 24 699923-1
117. Clays, K.; Wostyn, K.; Olbrechts, G.; Persoons, A.; Watanabe, A.; Nogi, K.; Duan, X.-M.; Okada, S.; Oikawa, H.; Nakanishi, H.; Vogel, H.; Beljonne, D.; Breédas, J.-L. J. Opt. Soc. Am. B 2000, 17, 256
118. Franz, E.; Harper, E. C.; Coe, B. J.; Zahradnik, P.; Clays, K.; Asselberghs, I. Proc. SPIE-Int. Soc. Opt. Eng. 2008, 6999, 699923
119. Heesink, G. J. T.; Ruiter, A. G. T.; van Hulst, N. F.; Boälger, B. Phys. Rev. Lett. 1993, 71, 999
120. Hendrickx, E.; Boutton, C.; Clays, K.; Persoons, A.; van Es, S.; Biemans, T.; Meijer, B. Chem. Phys. Lett. 1997, 270, 241
121. Boutton, C.; Clays, K.; Persoons, A.; Wada, T.; Sasabe, H. Chem. Phys. Lett. 1998, 286, 101
122. Shin, Y. K.; Brunschwig, B. S.; Creutz, C.; Sutin, N. J. Phys. Chem. 1996, 100, 8157
123. Coe, B. J.; Harris, J. A.; Brunschwig, B. S. J. Phys. Chem. A 2002, 106, 897
124. Liptay, W. In Excited States; Lim, E. C., Ed.; Academic Press: New York, 1974; Vol. 1, pp 129 - 229.
125. Bublitz, G. U.; Boxer, S. G. Annu. Rev. Phys. Chem. 1997, 48, 213
126. Vance, F. W.; Williams, R. D.; Hupp, J. T. Int. Rev. Phys. Chem. 1998, 17, 307
127. Brunschwig, B. S.; Creutz, C.; Sutin, N. Coord. Chem. Rev. 1998, 177, 61
128. Sheik-Bahae, M.; Said, A. A.; van Stryland, E. W. Opt. Lett. 1989, 14, 955
129. Sheik-Bahae, M.; Said, A. A.; Wei, T. H.; Hagan, D. J.; van Stryland, E. W. IEEE J. Quantum Electron. 1990, 26, 760
130. van Stryland, E. W.; Sheik-Bahae, M. Opt. Eng. 1998, 60, 655
131. Samoc, M.; Samoc, A.; Dalton, G. T.; Cifuentes, M. P.; Humphrey, M. G.; Fleitz, P. A. In Multiphoton Processes in Organics and Their Application; Rau, I.; Kajzar, F., Eds.; Old City Publishing: Philadelphia, 2010, in press.
132. Liang, M.; Xu, W.; Cai, F.-S.; Chen, P.-Q.; Peng, B.; Chen, J.; Li, Z.-M. J. Phys. Chem. C 2007, 111, 4465
133. Spangler, C. W.; McCoy, R. K. Synth. Commun. 1988, 18, 51
134. Nickel, E.; Spangler, C. W.; Rebane, A. Porphyrins with enhanced multi-photon absorption cross-sections for photodynamic therapy, U.S. Pat. 6,953,570, 2005.
135. Karthikeyan, C S.; Thelakkat, M. Inorg. Chim. Acta 2008, 361, 635
136. Coe, B. J.; Foxon, S. P.; Harper, E. C.; Harris, J. A.; Helliwell, M.; Raftery, J.; Asselberghs, I.; Clays, K.; Franz, E.; Brunschwig, B. S.; Fitch, A. G. Dyes Pigments 2009, 82, 171
137. Kuzuya, M.; Kondo, S.-I.; Murase, K. J. Phys. Chem. 1993, 97, 7800
138. Kwon, O.; Barlow, S.; Odom, S. A.; Beverina, L.; Thompson, N. J.; Zojer, E.; Breédas, J.-L.; Marder, S. R. J. Phys. Chem. A 2005, 109, 9346
139. Selected examples
140. Coe, B. J.; Houbrechts, S.; Asselberghs, I.; Persoons, A. Angew. Chem., Int. Ed. 1999, 38, 366
141. Weyland, T.; Ledoux, I.; Brasselet, S.; Zyss, J.; Lapinte, C. Organometallics 2000, 19, 5235
142. Malaun, M.; Reeves, Z. R.; Paul, R. L.; Jeffery, J. C.; McCleverty, J. A.; Ward, M. D.; Asselberghs, I.; Clays, K.; Persoons, A. Chem. Commun. 2001, 49
143. Powell, C. E.; Cifuentes, M. P.; Morrall, J. P.; Stranger, R.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B.; Heath, G. A. J. Am. Chem. Soc. 2003, 125, 602
144. Sporer, C.; Ratera, I.; Ruiz-Molina, D.; Zhao, Y.-X.; Vidal-Gancedo, J.; Wurst, K.; Jaitner, P.; Clays, K.; Persoons, A.; Rovira, C.; Veciana, J. Angew. Chem., Int. Ed. 2004, 43, 5266
145. Cifuentes, M. P.; Powell, C. E.; Morrall, J. P.; McDonagh, A. M.; Lucas, N. T.; Humphrey, M. G.; Samoc, M.; Houbrechts, S.; Asselberghs, I.; Clays, K.; Persoons, A.; Isoshima, T. J. Am. Chem. Soc. 2006, 128, 10819
146. Boubekeur-Lecaque, L.; Coe, B. J.; Clays K.; Foerier, S.; Verbiest, T.; Asselberghs, I. J. Am. Chem. Soc. 2008, 130, 3286
147. The structure of the Jd-containing salt (E)- N -methyl-4-[2-(2,3,6,7- tetrahydro-1 H,5 H -pyrido[3,2,1- ij ]quinolin-9-yl)ethenyl]pyridinium hexafluorophosphate is described partially in ref 39 and the average of the N(amino) - C(phenylene) distances for the two independent cations in the unit cell is 1.371(7) Å. We have also obtained a structure for (E)- N -methyl-4-[2-(4-diphenylaminophenyl)ethenyl]pyridinium hexafluorophosphate (Coe, B. J.; Helliwell, M.; Silverman, A. B., unpublished results) and this shows a N(amino) - C(phenylene) distance of 1.429(2) Å, clearly significantly longer than that in its Jd analogue and consistent with the stronger π -ED ability of Jd when compared with Dpap.
148. Mori, Y.; Matsuyama, Y.; Yamada, S.; Maeda, K. Acta Crystallogr., Sect. C 1992, 48, 894
149. Knoch, F.; Smauch, G.; Kisch, H. Z. Kristallogr. 1995, 210, 225
150. Wang, H.-L.; Xu, W.-Y.; Zhang, B.; Xiao, W.-J.; Wu, H. Acta Crystallogr., Sect. E 2009, 65, o149
151. Oudar, J. L.; Chemla, D. S. J. Chem. Phys. 1977, 66, 2664
152. Oudar, J. L. J. Chem. Phys. 1977, 67, 446
153. Coe, B. J.; Foxon, S. P.; Harper, E. C.; Helliwell, M.; Raftery, J.; Swanson, C. A.; Brunschwig, B. S.; Clays, K.; Franz, E.; Garién, J.; Orduna, J.; Horton, P. N.; Hursthouse, M. B. J. Am. Chem. Soc. 2010, 132, 1706
154. Coe, B. J.; Harris, J. A.; Asselberghs, I.; Wostyn, K.; Clays, K.; Persoons, A.; Brunschwig, B. S.; Coles, S. J.; Gelbrich, T.; Light, M. E.; Hursthouse, M. B.; Nakatani, K. Adv. Funct. Mater. 2003, 13, 347
155. See for example: Orr, B. J.; Ward, J. F. Mol. Phys. 1971, 20, 513
156. See for examples
157. Powell, C. E.; Morrall, J. P.; Ward, S. A.; Cifuentes, M. P.; Notaras, E. G. A.; Samoc, M.; Humphrey, M. G. J. Am. Chem. Soc. 2004, 126, 12234
158. Samoc, M.; Samoc, A.; Humphrey, M. G.; Cifuentes, M. P.; Luther-Davies, B.; Fleitz, P. A. Mol. Cryst. Liq. Cryst. 2008, 485, 994
159. See for examples
160. Das, S.; Nag, A.; Goswami, D.; Bharadwaj, P. K. J. Am. Chem. Soc. 2006, 128, 402
161. Drobizhev, M.; Stepanenko, Y.; Rebane, A.; Wilson, C. J.; Screen, T. E. O.; Anderson, H. L. J. Am. Chem. Soc. 2006, 128, 12432
162. Kim, K. S.; Noh, S. B.; Katsuda, T.; Ito, S.; Osuka, A.; Kim, D.-H. Chem. Commun. 2007, 2479
163. Collini, E.; Mazzucato, S.; Zerbetto, M.; Ferrante, C.; Bozio, R.; Pizzotti, M.; Tessore, F.; Ugo, R. Chem. Phys. Lett. 2008, 454, 70
164. Jana, A.; Jang, S. Y.; Shin, J.-Y.; Kumar De, A.; Goswami, D.; Kim, D.; Bharadwaj, P. K. Chem. - Eur. J. 2008, 14, 10628
165. Roberts, R. L.; Schwich, T.; Corkery, T. C.; Cifuentes, M. P.; Green, K. A.; Farmer, J. D.; Low, P. J.; Marder, T. B.; Samoc, M.; Humphrey, M. G. Adv. Mater. 2009, 21, 2318
166. Odom, S. A.; Webster, S.; Padilha, L. A.; Peceli, D.; Hu, H.-H.; Nootz, G.; Chung, S.-J.; Ohira, S.; Matichak, J. D.; Przhonska, O. V.; Kachkovski, A. D.; Barlow, S.; Brédas, J.-L.; Anderson, H. L.; Hagan, D. J.; Van Stryland, E. W.; Marder, S. R. J. Am. Chem. Soc. 2009, 131, 7510
167. Webster, S.; Odom, S. A.; Padilha, L. A.; Przhonska, O. V.; Peceli, D.; Hu, H.-H.; Nootz, G.; Kachkovski, A. D.; Matichak, J.; Barlow, S.; Anderson, H. L.; Marder, S. R.; Hagan, D. J.; Van Stryland, E. W. J. Phys. Chem. B 2009, 113, 14854
168. Padilha, L. A.; Webster, S.; Przhonska, O. V.; Hu, H.-H.; Peceli, D.; Ensley, T. R.; Bondar, M. V.; Gerasov, A. O.; Kovtun, Y. P.; Shandura, M. P.; Kachkovski, A. D.; Hagan, D. J.; Van Stryland, E. W. J. Phys. Chem. A 2010, 114, 6493
169. Xu, X.-L.; Qiu, W.-W.; Zhou, Q.; Tang, J.; Yang, F.; Sun, Z.-R.; Audebert, P. J. Phys. Chem. B 2008, 112, 4913