Coupling octupoles in crystals: The case of the 1,3,5-trinitrobenzene-triphenylene 1:1 molecular co-crystal

Chemistry of Materials

Volumn 15, Issue 16, 2003, Pages 3063-3073

  Zyss, Joseph ^a   Ledoux Rak, Isabelle ^a   Weiss, Hans Christoph ^b   Bläser, Dieter ^b   Boese, Roland ^b   Thallapally, Praveen K ^c   Thalladi, Venkat R ^c   Desiraju, Gautam R ^c  

^a LABORATOIRE DE PHOTONIQUE QUANTIQUE ET MOLÉCULAIRE   (France)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

^c UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHARGE TRANSFER; CRYSTAL LATTICES; NONLINEAR OPTICS; SUPRAMOLECULAR CHEMISTRY; X RAY DIFFRACTION ANALYSIS;

COUPLING OCTUPOLES;

MOLECULAR CRYSTALS;

COBALT; NITROBENZENE DERIVATIVE; TRINITROBENZENE; TRIPHENYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ENGINEERING; COUPLING OCTUPOLE; CRYSTAL; CRYSTAL STRUCTURE; MACROMOLECULE; MODEL; MOLECULAR INTERACTION; OPTICS; SURFACE CHARGE; X RAY DIFFRACTION;

EID: 0043027068     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm031018m     Document Type: Article

References (73)

1. Zyss, J., Ed. Molecular Nonlinear Optics: Materials, Physics and Devices; Academic Press: New York, 1994. Nalwa, H., Miyata, S., Eds. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: New York, 1996. Desiraju, G. R., Ed. Crystal Engineering; Elsevier Science: New York, 1989; Chapter 8 and references therein. Günter, P., Ed. Nonlinear Optical Effects and Materials; Springer Series in Optical Sciences; Springer: New York, 2000. Zyss, J. Ed. Molecular Photonics: Materials, Physics and Devices; C. R. Physique, Elsevier and Académie des Sciences: Paris, 2002; vol. 3 (4).
2. Zyss, J., Ed. Molecular Nonlinear Optics: Materials, Physics and Devices; Academic Press: New York, 1994. Nalwa, H., Miyata, S., Eds. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: New York, 1996. Desiraju, G. R., Ed. Crystal Engineering; Elsevier Science: New York, 1989; Chapter 8 and references therein. Günter, P., Ed. Nonlinear Optical Effects and Materials; Springer Series in Optical Sciences; Springer: New York, 2000. Zyss, J. Ed. Molecular Photonics: Materials, Physics and Devices; C. R. Physique, Elsevier and Académie des Sciences: Paris, 2002; vol. 3 (4).
3. Zyss, J., Ed. Molecular Nonlinear Optics: Materials, Physics and Devices; Academic Press: New York, 1994. Nalwa, H., Miyata, S., Eds. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: New York, 1996. Desiraju, G. R., Ed. Crystal Engineering; Elsevier Science: New York, 1989; Chapter 8 and references therein. Günter, P., Ed. Nonlinear Optical Effects and Materials; Springer Series in Optical Sciences; Springer: New York, 2000. Zyss, J. Ed. Molecular Photonics: Materials, Physics and Devices; C. R. Physique, Elsevier and Académie des Sciences: Paris, 2002; vol. 3 (4).
4. Zyss, J., Ed. Molecular Nonlinear Optics: Materials, Physics and Devices; Academic Press: New York, 1994. Nalwa, H., Miyata, S., Eds. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: New York, 1996. Desiraju, G. R., Ed. Crystal Engineering; Elsevier Science: New York, 1989; Chapter 8 and references therein. Günter, P., Ed. Nonlinear Optical Effects and Materials; Springer Series in Optical Sciences; Springer: New York, 2000. Zyss, J. Ed. Molecular Photonics: Materials, Physics and Devices; C. R. Physique, Elsevier and Académie des Sciences: Paris, 2002; vol. 3 (4).
5. Zyss, J., Ed. Molecular Nonlinear Optics: Materials, Physics and Devices; Academic Press: New York, 1994. Nalwa, H., Miyata, S., Eds. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: New York, 1996. Desiraju, G. R., Ed. Crystal Engineering; Elsevier Science: New York, 1989; Chapter 8 and references therein. Günter, P., Ed. Nonlinear Optical Effects and Materials; Springer Series in Optical Sciences; Springer: New York, 2000. Zyss, J. Ed. Molecular Photonics: Materials, Physics and Devices; C. R. Physique, Elsevier and Académie des Sciences: Paris, 2002; vol. 3 (4).
6. Oudar, J.-L. J. Chem. Phys. 1977, 67, 446. Levine, B. F.; Bethea, C. G. J. Chem. Phys. 1975, 63, 2666. Ledoux, I.; Zyss, J. Chem. Phys. 1982, 73, 203.
7. Oudar, J.-L. J. Chem. Phys. 1977, 67, 446. Levine, B. F.; Bethea, C. G. J. Chem. Phys. 1975, 63, 2666. Ledoux, I.; Zyss, J. Chem. Phys. 1982, 73, 203.
8. Oudar, J.-L. J. Chem. Phys. 1977, 67, 446. Levine, B. F.; Bethea, C. G. J. Chem. Phys. 1975, 63, 2666. Ledoux, I.; Zyss, J. Chem. Phys. 1982, 73, 203.
9. Terhune, R. W.; Maker, P. D.; Savage, C. M. Phys. Rev. Lett. 1965, 14, 681. Clays, K.; Persoons, A. Phys. Rev. Lett. 1991, 66, 2980. Zyss, J.; ChauVan, T.; Dhenaut, C.; Ledoux, I. Chem. Phys. 1993, 177, 281. Ray, P. C.; Das, P. K. J. Chem. Phys. 1995, 9, 9, 17891.
10. Terhune, R. W.; Maker, P. D.; Savage, C. M. Phys. Rev. Lett. 1965, 14, 681. Clays, K.; Persoons, A. Phys. Rev. Lett. 1991, 66, 2980. Zyss, J.; ChauVan, T.; Dhenaut, C.; Ledoux, I. Chem. Phys. 1993, 177, 281. Ray, P. C.; Das, P. K. J. Chem. Phys. 1995, 9, 9, 17891.
11. Terhune, R. W.; Maker, P. D.; Savage, C. M. Phys. Rev. Lett. 1965, 14, 681. Clays, K.; Persoons, A. Phys. Rev. Lett. 1991, 66, 2980. Zyss, J.; ChauVan, T.; Dhenaut, C.; Ledoux, I. Chem. Phys. 1993, 177, 281. Ray, P. C.; Das, P. K. J. Chem. Phys. 1995, 9, 9, 17891.
12. Terhune, R. W.; Maker, P. D.; Savage, C. M. Phys. Rev. Lett. 1965, 14, 681. Clays, K.; Persoons, A. Phys. Rev. Lett. 1991, 66, 2980. Zyss, J.; ChauVan, T.; Dhenaut, C.; Ledoux, I. Chem. Phys. 1993, 177, 281. Ray, P. C.; Das, P. K. J. Chem. Phys. 1995, 9, 9, 17891.
13. Oudar, J. L.; Zyss, J. Phys. Rev. A 1982, 26, 2016. Zyss, J.; Oudar, J. L. Phys. Rev. A 1982, 26, 2028.
14. Oudar, J. L.; Zyss, J. Phys. Rev. A 1982, 26, 2016. Zyss, J.; Oudar, J. L. Phys. Rev. A 1982, 26, 2028.
15. Zyss, J.; Nicoud, J. F.; Coquillay, M. J. Chem. Phys. 1984, 81, 4160.
16. Oudar, J-L.; Hierle, R. J. Appl. Phys. 1977, 48, 2699.
17. Zyss, J.; Chemla, D. S.; Nicoud, J-F. J. Chem. Phys. 1981, 74, 4800.
18. Meredith, G. R. In Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symposium Series 233, American Chemical Society: Washington, DC, 1983; Chapter 2, p 27. Masse, R.; Zyss, J. Mol. Eng. 1991, 1, 141; Khodja, S.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B. 1998, 15 (2), 751. Watanabe, O.; Noritake, T.; Okada, A.; Kurauchi, T. J. Mater. Chem. 1993, 3, 1053. Horiuchi, N.; Lefaucheux, F.; Ibanez, A.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B 2002, 19 (8), 1830.
19. Meredith, G. R. In Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symposium Series 233, American Chemical Society: Washington, DC, 1983; Chapter 2, p 27. Masse, R.; Zyss, J. Mol. Eng. 1991, 1, 141; Khodja, S.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B. 1998, 15 (2), 751. Watanabe, O.; Noritake, T.; Okada, A.; Kurauchi, T. J. Mater. Chem. 1993, 3, 1053. Horiuchi, N.; Lefaucheux, F.; Ibanez, A.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B 2002, 19 (8), 1830.
20. Meredith, G. R. In Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symposium Series 233, American Chemical Society: Washington, DC, 1983; Chapter 2, p 27. Masse, R.; Zyss, J. Mol. Eng. 1991, 1, 141; Khodja, S.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B. 1998, 15 (2), 751. Watanabe, O.; Noritake, T.; Okada, A.; Kurauchi, T. J. Mater. Chem. 1993, 3, 1053. Horiuchi, N.; Lefaucheux, F.; Ibanez, A.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B 2002, 19 (8), 1830.
21. Meredith, G. R. In Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symposium Series 233, American Chemical Society: Washington, DC, 1983; Chapter 2, p 27. Masse, R.; Zyss, J. Mol. Eng. 1991, 1, 141; Khodja, S.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B. 1998, 15 (2), 751. Watanabe, O.; Noritake, T.; Okada, A.; Kurauchi, T. J. Mater. Chem. 1993, 3, 1053. Horiuchi, N.; Lefaucheux, F.; Ibanez, A.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B 2002, 19 (8), 1830.
22. Meredith, G. R. In Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symposium Series 233, American Chemical Society: Washington, DC, 1983; Chapter 2, p 27. Masse, R.; Zyss, J. Mol. Eng. 1991, 1, 141; Khodja, S.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B. 1998, 15 (2), 751. Watanabe, O.; Noritake, T.; Okada, A.; Kurauchi, T. J. Mater. Chem. 1993, 3, 1053. Horiuchi, N.; Lefaucheux, F.; Ibanez, A.; Josse, D.; Zyss, J. J. Opt. Soc. Am. B 2002, 19 (8), 1830.
23. Zyss, J.; Masse, R.; Bagieu-Beucher, M.; Lévy, J. P. Adv. Mater. 1993, 5, 120.
24. Bhowmik, A.; Dharmadhikari, A.; Thakur, M. Observation of Spectral Narrowing and Mirrorless Lasing in SPCD. Paper presented at CLEO 99, Baltimore, MD; Paper CThQ5, 1999.
25. Marder, S. R.; Perry, J. W.; Schäfer, W. P. Science 1989, 245, 626; Knoepfle, R.; Schlesser, R.; Ducret, R.; Guenter, P. Nonlinear Opt. 1995, 9, 143. Thakur, M.; Xu, J.; Bhowmik, A.; Zhou, L. Appl. Phys. Lett. 1999, 74, 635-637. Kawase, K.; Mizuno, M.; Sohma, S.; Takahashi, H.; Taniuchi, T.; Urata, Y.; Wada, S.; Tashiro, H.; Ito, H. Optics Lett, 1999, 24, 1065-1067.
26. Marder, S. R.; Perry, J. W.; Schäfer, W. P. Science 1989, 245, 626; Knoepfle, R.; Schlesser, R.; Ducret, R.; Guenter, P. Nonlinear Opt. 1995, 9, 143. Thakur, M.; Xu, J.; Bhowmik, A.; Zhou, L. Appl. Phys. Lett. 1999, 74, 635-637. Kawase, K.; Mizuno, M.; Sohma, S.; Takahashi, H.; Taniuchi, T.; Urata, Y.; Wada, S.; Tashiro, H.; Ito, H. Optics Lett, 1999, 24, 1065-1067.
27. Marder, S. R.; Perry, J. W.; Schäfer, W. P. Science 1989, 245, 626; Knoepfle, R.; Schlesser, R.; Ducret, R.; Guenter, P. Nonlinear Opt. 1995, 9, 143. Thakur, M.; Xu, J.; Bhowmik, A.; Zhou, L. Appl. Phys. Lett. 1999, 74, 635-637. Kawase, K.; Mizuno, M.; Sohma, S.; Takahashi, H.; Taniuchi, T.; Urata, Y.; Wada, S.; Tashiro, H.; Ito, H. Optics Lett, 1999, 24, 1065-1067.
28. Marder, S. R.; Perry, J. W.; Schäfer, W. P. Science 1989, 245, 626; Knoepfle, R.; Schlesser, R.; Ducret, R.; Guenter, P. Nonlinear Opt. 1995, 9, 143. Thakur, M.; Xu, J.; Bhowmik, A.; Zhou, L. Appl. Phys. Lett. 1999, 74, 635-637. Kawase, K.; Mizuno, M.; Sohma, S.; Takahashi, H.; Taniuchi, T.; Urata, Y.; Wada, S.; Tashiro, H.; Ito, H. Optics Lett, 1999, 24, 1065-1067.
29. Brittain, S.; Paul, K.; Zhao, X.-M.; Whitesides, G. Physics World 1998, 11, 31-36. Bao, Z.; Rogers, J. A.; Katz, H. E. J. Mater. Chem. 1999, 9, 1905.
30. Brittain, S.; Paul, K.; Zhao, X.-M.; Whitesides, G. Physics World 1998, 11, 31-36. Bao, Z.; Rogers, J. A.; Katz, H. E. J. Mater. Chem. 1999, 9, 1905.
31. Miyata, S., Sasabe, H., Eds. Poled Polymers and their Applications to SHG and EO Devices. Gordon and Breach: Amsterdam, The Netherlands, 1997.
32. Ibanez, A.; Maximov, S.; Guiu, A.; Chaillout, C.; Baldeck, P. L. Adv. Mater. 1998, 10, 1540-1543. Thalladi, V. R.; Whitesides, G. M. J. Am. Chem. Soc. 2002, 124, 3520-3521.
33. Ibanez, A.; Maximov, S.; Guiu, A.; Chaillout, C.; Baldeck, P. L. Adv. Mater. 1998, 10, 1540-1543. Thalladi, V. R.; Whitesides, G. M. J. Am. Chem. Soc. 2002, 124, 3520-3521.
34. Zyss, J.; Ledoux, I.; Volkov, S. N.; Chernyak, V.; Mukamel, S.; Bartholomew, G. P.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 11956. Bartolomew, G. P.; Ledoux, I.; Mukamel, S.; Bazan, G. C.; Zyss, J. J. Am. Chem. Soc. 2002, 124, 13480.
35. Zyss, J.; Ledoux, I.; Volkov, S. N.; Chernyak, V.; Mukamel, S.; Bartholomew, G. P.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 11956. Bartolomew, G. P.; Ledoux, I.; Mukamel, S.; Bazan, G. C.; Zyss, J. J. Am. Chem. Soc. 2002, 124, 13480.
36. Zyss, J. J. Chem. Phys. 1993, 98, 6583-6599. Zyss, J. Nonlinear Optics 1991, 1, 3-18.
37. Zyss, J. J. Chem. Phys. 1993, 98, 6583-6599. Zyss, J. Nonlinear Optics 1991, 1, 3-18.
38. Ledoux, I.; Zyss, J.; Siegel, J. S.; Brienne, J.; Lehn, J. M. Chem. Phys. Lett. 1990, 172, 440.
39. Zyss, J.; Ledoux, I. Chem. Rev. 1994, 94, 77-105.
40. Brasselet, S.; Zyss, J. J. Opt. Soc. Am. B 1998, 15, 1, 208-210.
41. Fiorini, C.; Charra, F.; Nunzi, J-M.; Samuel, I. D. W.; Zyss, J. Opt. Lett. 1995, 20, 2469.
42. Braga, D.; Grepioni, F.; Desiraju, G. R. Chem. Rev. 1998, 98, 1375.
43. Cho, B. R.; Lee, S. J.; Lee, S. H.; Son, K. H.; Kim, Y. H.; Doo, J.-Y.; Lee, G. J.; Kang, T. I.; Lee, Y. K.; Cho, M.; Jeon, S.-J. Chem. Mater. 2001, 13 (5), 1438-1440.
44. Donval, A.; Toussaere, E.; Brasselet, S.; Zyss, J. Opt. Mater. 1999, 12, 215.
45. Choi, I. S.; Li, X.; Simanek, E. E.; Akaba, R.; Whitesides, G. M. Chem. Mater. 1999, 11, 684-690.
46. Thalladi, V. R.; Brasselet, S.; Weiss, H-C.; Bläser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563.
47. Foster, R. Organic Charge-Transfer Complexes. Academic: New York, 1969.
48. Allen, F. H.; Kennard, O. Chem. Des. Autom. News 1993, 8, 1.
49. The seven acceptors are TNB, TCNQ, bis(ethylenedithio)-tetrathiafulvalene, 2,2′-bi-1,3-dithiole, pyromellitic dianhydride, mellitic trianhydride, and benzoquinone derivatives (mainly chloranil and DDQ).
50. Ahmed, F. R,; Trotter, J. Acta Crystallogr. 1963, 16, 503.
51. 1. Thallapally, P. K.; Katz, A. K.; Carrell, H. L.; Desiraju, G. R. manuscript in preparation.
52. 1. Thallapally, P. K.; Katz, A. K.; Carrell, H. L.; Desiraju, G. R. manuscript in preparation.
53. Desiraju, G. R.; Krishna, T. S. R. Mol. Cryst. Liq. Cryst. 1989, 159, 277.
54. Thalladi, V. R.; Panneerselvam, K.; Carrell, C. J.; Carrell, H. L.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1995, 341.
55. Thallapally, P. K.; Chakraborty, K.; Carrell, H. L.; Kotha, S.; Desiraju, G. R. Tetrahedron 2000, 56, 6721.
56. Biradha, K.; Nangia, A.; Desiraju, G. R.; Carrell, C. J.; Carrell, H. L. J. Mater. Chem. 1997, 7, 1111.
57. Carrell, H. L.; Glusker, J. P. Struct. Chem. 1997, 8, 141.
58. Batten, S. R.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 1460.
59. Sharma, C. V. K.; Zaworotko, M. J. Chem. Commun. 1996, 2655.
60. (a) Thalladi, V. R.; Brasselet, S.; Weiss, H.-C.; Blasér, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563.
61. (b) Thalladi, V. R.; Brasselet, S.; Blaser, D.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju. Chem. Commun. 1997, 1841.
62. (c) Filippini, G.; Gavezzotti, A. Chem. Phys. Lett. 1994, 231, 86.
63. (d) Wortmann, R.; Glania, C.; Krämer, P.; Matschiner, R.; Wolff, J. J.; Kraft, S.; Treptow, B.; Barbu, E.; Längle, D.; Görlitz, G. Chem. Eur. J. 1997, 3, 1765.
64. (e) Wolff, J. J.; Siegler, F.; Matschiner, R.; Wortmann, R. Angew. Chem., Int. Ed. 2000, 39, 1436.
65. (f) Cho, B. R.; Park, S. B.; Lee, S. J.; Son, K. H.; Lee, S. H.; Lee, M. ; Yoo, J.; Lee, Y. K.; Lee, G. J.; Kang, T. I,; Cho, M.; Jeon, S. J. J. Am. Chem. Soc. 2001, 123, 6421.
66. Kotler, Z.; Hierle, R.; Josse, D.; Zyss, J.; Masse, R. J. Opt. Soc. Am. B 1992, 9, 534.
67. Andraud, C.; Zabulon, T.; Collet, A.; Zyss, J. Chem. Phys. 1999, 245, 243.
68. Le Bozec, H.; Le Bouder, T.; Maury, O.; Bondon, A.; Ledoux, I.; Deveau, S.; Zyss, J. Adv. Mater. 2001, 22, 1677. Dhenaut, C.; Ledoux, I.; Samuel, I.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339.
69. Le Bozec, H.; Le Bouder, T.; Maury, O.; Bondon, A.; Ledoux, I.; Deveau, S.; Zyss, J. Adv. Mater. 2001, 22, 1677. Dhenaut, C.; Ledoux, I.; Samuel, I.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339.
70. Zyss, J.; Berthier, G. J. Chem. Phys. 1982, 77, 3635. Rérat, M.; Zyss, J. Work in progress.
71. Zyss, J.; Berthier, G. J. Chem. Phys. 1982, 77, 3635. Rérat, M.; Zyss, J. Work in progress.
72. Zyss, J.; Brasselet, S.; Thalladi, V. R.; Desiraju, G. R. J. Chem. Phys. 1998, 109, 658.
73. Zyss, J.; Boulanger, B. In International Tables for Crystallography, Volume D Physical Properties; Authier, A., Ed., Kluwer: Boston, MA, In press 2003.