Second order nonlinear optical networks with excellent poling stability from a new trifunctional thiophene based chromophore

Organic Electronics

Volumn 10, Issue 1, 2009, Pages 53-60

  Borbone, Fabio ^a   Caruso, Ugo ^a   Diana, Rosita ^a   Panunzi, Barbara ^a   Roviello, Antonio ^a   Tingoli, Marco ^a   Tuzi, Angela ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Crosslinked material; NLO properties; Thiophene dye

Indexed keywords

CHROMOPHORES; CRYSTAL STRUCTURE; HARMONIC GENERATION; OPTICAL PROPERTIES; THIOPHENE;

CROSS-LINKED MATERIALS; DIPOLE ORDERING; MAKER FRINGE TECHNIQUE; NLO PROPERTIES; SECOND-ORDER NONLINEAR OPTICAL; SECOND-ORDER NONLINEAR OPTICAL PROPERTY; TEMPORAL STABILITY; THIOPHENE DYES;

NONLINEAR OPTICS;

EID: 58049165195     PISSN: 15661199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orgel.2008.10.004     Document Type: Article

References (49)

1. Y. Yabuki, T. Chino, T. Fujiwara, EP Patent # 1437387, 2004.
2. A.T. Leaver, WO Patent # 9704030, 1997.
3. Seed A., Cross G.J., Toyne K.J., and Goodby J.W. Liq. Cryst. 30 9 (2003) 1089
4. Tong L., Wang J., Jian X., and Zhang Q. Gongneng Gaofenzi Xuebao 17 3 (2004) 535
5. Michaleviciute A., Buika G., Grazulevicius J.V., Tran-Van F., Chevrot C., and Jankuaskas V. Mol. Cryst. Liq. Cryst. 468 (2007) 459
6. Moylan C.R., McNelis B.J., Nathan L.C., Marques M.A., Hermstad E.L., and Brichler B.A. J. Org. Chem. 69 24 (2004) 8239
7. Jen A.K.-Y., Pushkara Rao V., Wong K.Y., and Drost K.J. J. Chem. Soc., Chem. Commun. (1993) 90
8. Yuquan S., Yuxia Z., Zao L., Jianghong W., Ling Q., Shixiong L., Jianfeng Z., and Jiayun Z. J. Chem. Soc., Perkin Trans. 1 (1999) 3691
9. Guo K., Hao J., Zhang T., Zu F., Zhai J., Qiu L., Zhen Z., Liu X., and Shen Y. Dyes Pigments 77 (2008) 657
10. Varanasi P.R., Jen A.K.-Y., Chandrasekhar J., Namboothiri I.N.N., and Rathna A. J. Am. Chem. Soc. 118 (1996) 12443
11. Albert I.D.L., Morley J.O., and Pugh D. J. Phys. Chem. 99 (1995) 8024
12. Breitung E.M., Shu C.-F., and McMahon R.J. J. Am. Chem. Soc. 122 (2000) 1154
13. Xu H., Yin S., Zhu W., Song Y., and Tang B. Polymer 47 (2006) 6986
14. Zhang C., Wang C., Dalton L.R., Zhang H., and Steier W.H. Macromolecules 34 (2001) 253
15. Yuxia Z., Zhao L., Ling Q., Jianfen Z., Jiayun Z., Yuquan S., Gang X., and Peixian Y. European Polym. J. 37 (2001) 445
16. Kim D.W., Choi J.J., Lim J.-S., and Lee C. Mol. Cryst. Liq. Cryst. 463 (2007) 325
17. Zu F.-H., Qiu L., Shen Y.-Q., Deng X.-X., Zhou J.-H., Shen Q.-S., and Cao Z.-Q. Gaodeng Xuexiao Huaxue Xuebao 27 3 (2006) 562
18. Y. Shen, L. Qiu, F. Zu, T. Zhang, K. Guo, CN Patent # 1814595, 2006.
19. Monnereau C., Blart E., Illien B., Paris M., and Odobel F. J. Phys. Org. Chem. 18 (2005) 1050
20. Apostoluk A., Nunzi J.-M., Boucher V., Essahlaoui A., Seveno R., Gundel H.W., Monnereau C., Blart E., and Odobel F. Opt. Commun. 260 (2006) 708
21. Hao J., Han M.-J., Guo K., Zhai J., Zhang T., Meng X., Liang J., Qiu L., and Shen Y. React. Funct. Polym. 67 8 (2007) 758
22. Tsutsumi N., Yoshizaki S., Sakai W., and Kiyotsukuri T. Macromolecules 28 (1995) 6437
23. Kim T.-D., Luo J., Ka J.-W., Hau S., Tian Y., Shi Z., Tucker N.M., Jang S.-H., Kang J.-W., and Jen A.K.-J. Adv. Mater. 18 (2006) 3038
24. M. Onishi, H. Matsumoto, JP Patent # 01266167, 1989.
25. Morley J.O., Guy O.J., and Charlton M.H. J. Phys. Chem. A 108 (2004) 10542
26. Morley J.O., Guy O.J., and Charlton M.H. J. Photochem. Photobiol. A: Chem. 173 (2005) 174
27. Dalton L.R., Harper A.W., Ghosn R., Steier W.H., Ziari M., Fetterman H., Shi Y., Mustacich R.V., Jen A.K.-Y., and Shea K.J. Chem. Mater. 7 (1995) 1060
28. Caruso U., Casalboni M., Fort A., Fusco M., Panunzi B., Quatela A., Roviello A., and Sarcinelli F. Opt. Mater. 27 12 (2005) 1800
29. Albert I.D.L., Marks T.J., and Ratner M.A. J. Am. Chem. Soc. 119 (1997) 6575
30. Morley J.O., and Pugh D. J. Chem. Soc. Faraday Trans. 87 18 (1991) 3021
31. Angeloni A.S., Laus M., Castellari C., Galli G., Ferruti P., and Chiellini E. Makromol. Chem. 186 (1985) 977
32. Wu D., Liu Y., He C., Chung T., and Goh S. Macromolecules 37 (2004) 6763
33. A drawback of poling efficiency due to film conductivity should be excluded, taking in account that a relevant attainment of charged species during the crosslinking/poling process seems not in keep with the chemistry of the system, and that no film corrosion was observed in the experiment.
34. March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. fourth ed. (1992), Wiley, New York, NY
35. This approach could be compared with the well known use of the reaction of the epoxy groups with phenolic [38] or carboxylic [39] groups for the attainment of NLO active networks.
36. Dalton L.R., Harper A.W., and Robinson B.H. Proc. Natl. Acad. Sci. USA 94 (1997) 4842
37. Fusco S., Centore R., Riccio P., Quatela A., Stracci G., Archetti G., and Kuball H.-G. Polymer 49 (2008) 186
38. Zhang L.Z., Li Y., Liang Z.X., Yu Q.S., and Cai Z.G. React. Funct. Polym. 40 (1999) 255
39. Bosc D., Foll F., Boutevin B., and Rousseau A. J. Appl. Polym. Sci. 74 4 (1999) 974
40. Wang H.H., and Yuen U.E. J. Appl. Polym. Sci. 102 (2006) 607
41. Baigrie B.D. Res. Disclos. 175 (1978) 32
42. Caruso U., Diana R., Fort A., Panunzi B., and Roviello A. Macromol. Symp. 234 (2006) 87
43. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G., and Spagna R. J. Appl. Cryst. 32 (1999) 115
44. Sheldrick G.M. SHELXL-97 Program (1997), University of Göttingen, Germany
45. All crystallographic data have been deposited at the Cambridge Crystallographic Data Centre (CCDC). Deposition number is CCDC 685786. These data can be obtained at free of charge.
46. Herman W.N., and Hayden L.M. J. Opt. Soc. Am. B 12 3 (1995) 416
47. Shoji I., Kondo T., and Ito R. Opt. Quant. Electron. 34 (2002) 797
48. Kleinman D.A. Phys. Rev. 126 (1962) 1977
49. Williams D.J. Nonlinear optical properties of guest-host polymer structures. In: Chemla D.S., and Zyss J. (Eds). Nonlinear Optical Properties of Organic Molecules and Crystals (1987), Academic, Orlando, FL