An azo-bridged ferroelectric liquid crystal with highly enhanced second and third harmonic generation

Journal of the American Chemical Society

Volumn 134, Issue 39, 2012, Pages 16298-16306

  Zhang, Yongqiang ^a   Ortega, Josu ^b   Baumeister, Ute ^c   Folcia, César L ^b   Sanz Enguita, Gerardo ^b   Walker, Christopher ^a   Rodriguez Conde, Sofía ^b   Etxebarria, Jesus ^b   O'Callaghan, Michael J ^a   More, Kundalika ^a  

^a MICRON TECHNOLOGY INC   (United States)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^c MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BISTABLES; BOOKSHELF GEOMETRY; ELECTRO-OPTICAL MEASUREMENTS; FERROELECTRIC LIQUID CRYSTAL; FERROELECTRIC SWITCHING; INNOVATIVE APPROACHES; MESOGENES; NONLINEAR OPTICAL; POLAR AXIS; RESONANCE WAVELENGTHS; SECOND AND THIRD HARMONICS; SECOND HARMONICS; THERMODYNAMICALLY STABLE; THIRD-ORDER NONLINEAR SUSCEPTIBILITY;

CHROMOPHORES; DIFFERENTIAL SCANNING CALORIMETRY; FERROELECTRICITY; LIQUID CRYSTALS; NONLINEAR OPTICS; OLIGOMERS; OPTICAL DATA PROCESSING; OPTICAL MICROSCOPY; X RAY DIFFRACTION ANALYSIS;

HARMONIC GENERATION;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOPHORE; DIFFERENTIAL SCANNING CALORIMETRY; ENANTIOSELECTIVITY; FERROELECTRIC LIQUID CRYSTAL; GEOMETRY; LIQUID CRYSTAL; MICROSCOPY; NONLINEAR OPTICS; OPTICS; SECOND HARMONIC GENERATION; SPECTRAL SENSITIVITY; SYNTHESIS; THERMODYNAMICS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 84867093321     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3062826     Document Type: Article

References (67)

1. Shi, Y.; Zhang, C.; Zhang, H.; Bechtel, J. H.; Dalton, L. R.; Robinson, B. H.; Steier, W. H. Science 2000, 288, 119
2. Lee, M.; Katz, H. E.; Erben, C.; Gill, D. M.; Gopalan, P.; Heber, J. D.; McGee, D. J. Science 2002, 298, 1401
3. Hales, J. M.; Matichak, J.; Barlow, S.; Ohira, S.; Yesudas, K.; Bredas, J.-L.; Perry, J. W.; Marder, S. R. Science 2010, 327, 1485-1488
4. Nonlinear optics of organic molecules and polymers; Nalwa, H. S.; Miyata, S., Eds.; CRC Press, Inc: Boca Raton, FL, 1996.
5. Yitzchaik, S.; Marks, T. J. Acc. Chem. Res. 1996, 29, 197-202
6. Marder, S. R. Chem. Commun. 2006, 131
7. Innocenzi, P.; Lebeau, B. J. Mater, Chem. 2005, 15, 3821
8. Coe, B. J. Acc. Chem. Res. 2006, 39, 383
9. Sullivan, P. A.; Dalton, L. R. Acc. Chem. Res. 2010, 433, 10-18
10. Dalton, L. R.; Sullivan, P. A.; Bale, D. H. Chem. Rev. 2010, 110, 25-55
11. Lagerwall, S. T. Ferroelectric and antiferroelectric liquid crystals; Wiley-VCH: Weinheim, Germany, 1999.
12. Zhang, Y.; Etxebarria, J. Ferroelectric liquid crystals for nonlinear optical applications. In Liquid crystals beyond displays; Li, Quan, Ed.; Wiley: Hoboken, NJ, 2012, 111-156.
13. Champagne, B.; Guthmuller, J.; Perreault, F.; Soldera, A. J. Phys. Chem. C 2012, 116, 7552-7560
14. Etxebarria, J.; Ros, M. B. J. Mater. Chem. 2008, 18, 2919-2926
15. Lee, S. K.; Heo, S.; Lee, J. G.; Kang, K.-T.; Kumazawa, K.; Nishida, K.; Shimbo, Y.; Takanishi, Y.; Watanabe, J.; Doi, T.; Takahashi, T.; Takezoe, H. J. Am. Chem. Soc. 2005, 127, 11085-11091
16. Hennrich, G.; Omenat, A.; Asselberghs, I.; Foerier, S.; Clays, K.; Verbiest, T.; Serrano, J. L. Angew. Chem., Int. Ed. 2006, 45, 4203-4206
17. Gorecka, E.; Pociecha, D.; Matraszek, J.; Mieczkowski, J.; Shimbo, Y.; Takanishi, Y.; Takezoe, H. Phys. Rev. E 2006, 73, 031704
18. Okada, Y.; Matsumoto, S.; Takanishi, Y.; Ishikawa, K.; Nakahara, S.; Kishikawa, K.; Takezoe, H. Phys. Rev. E 2005, 72, 020701(R)
19. Miyajima, D.; Araoka, F.; Takezoe, H.; Kim, J.; Kato, K.; Takata, M.; Aida, T. Science 2012, 336, 209
20. Hough, L. E.; Jung, H. T.; Krüerke, D.; Heberling, M. S.; Nakata, M.; Jones, C. D.; Chen, D.; Link, D. R.; Zasadzinski, J.; Heppke, G.; Rabe, J. P.; Stocker, W.; Körblova, E.; Walba, D. M.; Glaser, M. A.; Clark, N. A. Science 2009, 325, 456-460
21. Koike, M.; Yen, C.-C.; Liu, Y.; Tsuchiya, H.; Tokita, M.; Kawauchi, S.; Takezoe, H.; Watanabe, J. Macromolecules 2007, 40, 2524-2531
22. Drevensek-Olenik, I.; Copic, M. Phys Rev. E 1997, 56, 581-591
23. Hoshi, H.; Chung, D. H.; Ishikawa, K.; Takezoe, H. Phys. Rev. E 2001, 63, 056610
24. Yoo, J. G.; Choi, S. W.; Hoshi, H.; Ishikawa, K.; Takezoe, H.; Schadt, M. Jpn. J. Appl. Phys. 1997, 36, L1168-L1171
25. Cai, W.; Vasudev, A. P.; Brongersma, M. L. Science 2011, 333, 1720-1723
26. Verbiest, T.; Houbrechts, S.; Kauranen, M.; Clays, K.; Persoons, A. J. Mater. Chem. 1997, 7, 2175-2189
27. Dalton, L. R.; Steier, W. H.; Robinson, B. H.; Zhang, C.; Ren, A.; Garner, S.; Chen, A.; Londergan, T.; Irwin, L.; Carlson, B.; Fifield, L.; Phelan, G.; Kincaid, C.; Amend, J.; Jen, Al. J. Mater. Chem. 1999, 9, 1905-1920
28. Shtykov, N. M.; Barnik, M. I.; Beresnev, L. A.; Blinov, L. M. Mol. Cryst. Liq. Cryst. 1985, 124, 379-390
29. Walba, D. M.; Ros, M. B.; Clark, N. A.; Shao, R.; Robinson, M. G.; Liu, J. Y.; Johnson, K. M.; Doroski, D. J. J. Am. Chem. Soc. 1991, 113, 5471-5474
30. Yoshino, K.; Utsumi, M.; Morita, Y.; Sadohara, Y.; Ozaki, M. Liq. Cryst. 1993, 14, 1021-1032
31. Trollsås, M.; Orrenius, C.; Sahlén, F.; Gedde, U. W.; Norin, T.; Hult, A.; Hermann, D.; Rudquist, P.; Komitov, L.; Lagerwall, S. T.; Lindström, J. J. Am. Chem. Soc. 1996, 118, 8542-8548
32. Artal, C.; Ros, M. B.; Serrano, J. L.; Pereda, N.; Etxebarria, J.; Folcia, C. L.; Ortega, J. Macromolecules 2001, 34, 4244-4255
33. Schmitt, K.; Herr, R.-P.; Schadt, M.; Funfschilling, J.; Buchecker, R.; Chen, X. H.; Benecke, C. Liq. Cryst. 1993, 14, 1735-1752
34. Keller, P.; Shao, R.; Walba, D. M.; Brunet, M. Liq. Cryst. 1995, 18, 915-918
35. Walba, D. M.; Keller, P.; Shao, R.; Clark, N. A.; Hillmyer, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2740-2741
36. Fazio, V. S. U.; Lagerwall, S. T.; Zauls, V.; Schrader, S.; Busson, P.; Hult, A.; Motschmann, H. Eur. Phys. J. E: Soft Matter Biol. Phys. 2000, 3, 245-251
37. Trollsås, M.; Sahlén, F.; Gedde, U. W.; Hult, A.; Hermann, D.; Rudquist, P.; Komitov, L.; Lagerwall, S. T.; Stebler, B.; Lindström, J.; Rydlund, O. Macromolecules 1996, 29, 2590-2598
38. Espinet, P.; Etxebarria, J.; Folcia, C. L.; Ortega, J.; Ros, M. B.; Serrano, J. L. Adv. Mater. 1996, 8, 745-748
39. Ozaki, M.; Utsumi, M.; Gotou, T.; Morit, Y.; Daido, K.; Sadohara, Y.; Yoshino, K. Ferroelectrics 1991, 121, 259-274
40. Walba, D. M.; Dyer, D. J.; Sierra, T.; Cobben, P. L.; Shao, R.; Clark, N. A. J. Am. Chem. Soc. 1996, 118, 1211
41. Walba, D. M.; Xiao, L.; Keller, P.; Shao, R.; Link, D.; Clark, N. A. Pure Appl. Chem. 1999, 71, 2117
42. Walba, D. M.; Xiao, L.; Korblova, E; Keller, P.; Shoemaker, R.; Nakata, M.; Shao, R.; Link, D. R.; Coleman, D. A.; Clark, N. A. Ferroelectrics 2004, 309, 77
43. Zhang, Y.; Martinez-Perdiguero, J.; Baumeister, U.; Walker, C.; Etxebarria, J.; Prehm, M.; Ortega, J.; Tschierske, C.; O'Callaghan, M. J.; Harant, A.; Handschy, M. J. Am. Chem. Soc. 2009, 131, 18386-18392
44. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849
45. 3 should be used instead of 1.4 g mentioned in the experimental procedure of this reference.
46. Dierking, I.; F. Gießelmann, F.; Zugenmaier, P. Liq. Cryst. 1994, 17, 17-22
47. Dierking, I. Liq. Cryst. 1999, 26, 83-95
48. Kašpar, M.; Novotná, V.; Glogarová, M.; Hamplová, V.; Pociech, D. Liq. Cryst. 2010, 37, 129-137
49. Pereda, N.; Folcia, C. L.; Etxebarria, J.; Ortega, J.; Ros, M. B. Liq. Cryst. 1998, 24, 451
50. Belyakov, V. A.; Shipov, N. V. Phys. Lett. 1981, 86A, 94-97
51. Etxebarria, J.; Ortega, J.; Folcia, C. L.; Zhang, Y.; Walker, C. Phys. Rev. E submitted.
52. The full name of the chromophore is N, N -diethyl-4-((E)-(4-((E)-(4- nitrophenyl)diazenyl)phenyl)diazenyl)aniline. It can be readily synthesized by following an approach to an analogue in the following reference. Amano, M.; Kaino, T. J. Appl. Phys. 1990, 68, 6024
53. Cheng, L. T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.; Rikken, G.; Marder, S. R. J. Phys. Chem. 1991, 95, 10631-10643
54. Suzuki, H.; Hiratsuka, H. Proc. SPIE 1988, 971, 97
55. Spackman, M. A. J. Phys. Chem. 1989, 93, 7594
56. Martinez-Perdiguero, J.; Zhang, Y.; Walker, C.; Etxebarria, J.; Folcia, C. L.; Ortega, J.; O'Callaghan, M. J.; Baumeister, U. J. Mater. Chem. 2010, 20, 4905-4909
57. -2).
58. Kaino, T.; Tomaru, S.; Kurihara, T.; Amano, M. Mater. Res. Soc. Symp. Proc. 1992, 247, 179-190
59. (3) from THG. Nalwa, H. S. Adv. Mater. 1993, 5, 341-358
60. Kurihara, T.; Kabayashi, H.; Kubodera, K.; Kaino, T. Opt. Commun. 1991, 84, 149-154
61. Smith, D. A.; Coles, H. J. Liq. Cryst. 1993, 14, 937
62. Ortega, J.; Gallastegui, J. A.; Folcia, C. L.; Etxebarria, J.; Gimeno, N.; Ros, M. B. Liq. Cryst. 2004, 31, 579-584
63. Macdonald, R.; Kentischer, F.; Warnick, P.; Heppke, G. Phys. Rev. Lett. 1998, 81, 4408-4411
64. Araoka, F.; Thisayukta, J.; Ishikawa, K.; Watanabe, J.; Takezoe, H. Phys. Rev. E 2002, 66, 021705
65. Folcia, C. L.; Alonso, I.; Ortega, J.; Etxebarria, J.; Pintre, I.; Ros, M. B. Chem. Mater. 2006, 18, 4617
66. Pintre, I. C.; Gimeno, N.; Serrano, J. L.; Ros, M. B.; Alonso, I.; Folcia, C. L.; Ortega, J.; Etxebarria, J. J. Mater. Chem. 2007, 17, 2219-2227
67. Pintre, I. C.; Serrano, J. L.; Ros, M. B.; Martinez-Perdiguero, J.; Alonso, I.; Ortega, J.; Folcia, C. L.; Etxebarria, J.; Alicante, R.; Villacampa, B. J. Mater. Chem. 2010, 20, 2965-2971.