The synthesis and properties of novel diazo chromophores based on thiophene conjugating spacers and tricyanofuran acceptors

Dyes and Pigments

Volumn 77, Issue 3, 2008, Pages 657-664

  Guo, Kunpeng ^a,b   Hao, Jumin ^b   Zhang, Tao ^b   Zu, Fenghua ^b   Zhai, Jianfeng ^b   Qiu, Ling ^b   Zhen, Zhen ^b   Liu, Xinhou ^b   Shen, Yuquan ^b  

^a UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^b TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

Chromophore; Diazo; EO; NLO; TCF; Thiophene

Indexed keywords

CHARACTERIZATION; CHROMOPHORES; ELECTROOPTICAL EFFECTS; NONLINEAR OPTICS; THERMODYNAMIC STABILITY;

CONJUGATING SPACERS; THIOPENE; TRICYANOFURAN;

AZO DYES;

AZO DYE; CALORIMETRY; DYE PROPERTY; SYNTHESIS; THERMAL STABILITY; THERMOGRAVIMETRY;

EID: 36348995355     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2007.09.006     Document Type: Article

References (57)

1. Marder S.R., Kippelen B., Jen A.K.Y., and Peyghambarian N. Nature 388 (1997) 845
2. Sandhya K.Y., Chennakata K.S.P., and Naoto T. Prog Polym Sci 29 (2004) 45
3. Shi Y.Q., Lin W.P., Olson D.J., and Bechtel J.H. Appl Phy Lett 77 (2000) 1
4. Chen D., Fetterman H.R., Chen A., Steier W.H., Dalton L.R., Wang W., and Shi Y. Appl Phys Lett 70 (1997) 3335
5. Shi Y.Q., Zhang C., Zhang H., Bechtel J.H., Dalton L.R., and Robinson B.H. Science 288 (2000) 119
6. Burland D.M., Miller R.D., and Walsh C.A. Chem Rev 94 (1994) 31
7. Dalton L.R. J Phys: Condens Matter 15 (2003) 897
8. Liu S., Haller M.A., Ma H., Dalton L.R., Jang S.H., and Jen A.K.Y. Adv Mater 15 (2003) 603
9. Zhang C., Wang C.G., Yang J.L., Dalton L.R., San G.L., Zhang H., and Steier W.H. Macromolecules 34 (2001) 235
10. Zhang C., Dalton L.R., Oh M.C., Zhang H., and Steier W.H. Chem Mater 13 (2001) 3043
11. He M.Q., Lescie T.M., and Sinicropl J.A. Chem Mater 14 (2002) 4662
12. He M.Q., Lescie T.M., Sinicropl J.A., Garner S.M., and Reed L.D. Chem Mater 14 (2002) 4669
13. He M.Q., Lescie T.M., and Sinicropl J.A. Chem Mater 14 (2002) 2393
14. Dalton L.R., Steier W.H., Robinson B.H., Zhang C., Ren A., Garner S., et al. J Mater Chem 9 (1999) 1905
15. Wu W., Zhang Z.L., and Zhang X.Y. J Chem Res 2004 (2004) 617
16. Bu X.R., Li H.Y., Derveer D.V., and Mintz E.A. Tetrahedron Lett 37 (1996) 7331
17. Jen A.K.-Y., Liu Y.Q., Zheng L.X., Liu S., Drost K.J., Zhang Y., and Dalton L.R. Adv Mater 11 (1999) 452
18. Spraul B.K., Suresh S., Sassa T., Herranz M.A., Echegoyen L., Wada T., et al. Tetrahedron Lett 45 (2004) 3253
19. Blanchard P., Raimundo J.-M., and Roncali J. Synth Metals 119 (2001) 527
20. Raimundo J.-M., Blanchard P., Gallego-Planas N., Mercier N., Ledoux-Rak I., Hierle R., and Roncali J. J Org Chem 67 (2002) 205
21. Hu Z.-Y., Fort A., Barzoukas M., Jen A.K.-Y., Barlow S., and Marder S.R. J Phys Chem B 108 (2004) 8626
22. Santos J., Mintz E.A., Zehnder O., Bosshard C., Bu X.R., and Gunter P. Tetrahedron Lett 42 (2001) 805
23. Zadrozna I., and Kaczorowska E. Dyes Pigments 71 (2006) 207
24. Chen L.J., Cui Y.J., Qian G.D., and Wang M.Q. Dyes Pigments 73 (2007) 338
25. Trofimov B.A., Schmidt E.Y., Mikhaleva A.I., Vasil'tsov A.M., Zaitsev A.B., Smolyanina N.S., et al. Eur J Org Chem (2006) 4021
26. Qian Y., Wang G., Xiao G.M., Lin B.P., and Cui Y.P. Dyes Pigments 75 (2007) 460
27. Ledoux I., Zyss J., Barni E., Barolo C., Diulgheroff N., Quagliotto P., and Viscardi G. Synth Metals 115 (2000) 213
28. Miller R.D., Burland D.M., Jurich M., Lee V.Y., Moylan C.R., and Volksen W. Nonlinear Opt 15 (1996) 343
29. Moylan C.R., McNelis B.J., Nathan L.C., Marques M.A., Hermstad E.L., and Brichler B.A. J Org Chem 69 (2004) 8239
30. Qiu L., Shen Y.Q., Hao J.M., Zu F.H., Zhang T., Zhao Y.X., et al. J Mater Sci 39 (2004) 2335
31. Hao JM, Han MJ, Guo KP, Zhao YX, Qiu L, Shen YQ, Meng XG. Mater. Lett., in press.
32. Tour J.M., and Wu R.L. Macromolecules 25 (1992) 1901
33. Akoudad S., Frere P., Mercier N., and Roncali J. J Org Chem 64 (1999) 4267
34. Solladie-Cavallo A., and Vieles P. Bull Soc Chim Fr 2 (1967) 517
35. Overberger C.G., and Lal J. J Am Chem Soc 73 (1951) 2956
36. Coffey M., Mckellar B.R., Reinhardt B.A., Nijakowski T., and Feld W.A. Synth Commun 26 (1996) 2205
37. Patrick T.M., and Emerson W.S. J Am Chem Soc 74 (1952) 1356
38. Woodward R.B. Org Synth Coll vol. 3 (1955) 453
39. Cheng L.T., Tam W., Stevenson S.H., and Meredith G.R. J Phys Chem 95 (1991) 10631
40. Burland D.M., Rice J.E., and Stähelin M. Mol Cryst Liq Cryst 216 (1992) 27
41. Masafumi A., Yukichi M., and Shinichiro N. J Org Chem 58 (1993) 5238
42. DeMartino R.N., Choe E.W., Khanarian G., Haas D., Leslie T., Nelson G., et al. In: Prasad P.N., and Ulrich D.R. (Eds). Nonlinear Optical and Electroactive Polymers (1988), Plenum Press, New York 169-186
43. Raposo M.M.M., Sousa A.M.R.C., Kirsch G., Cardoso P., Belsley M., Gomes E.M., et al. Org Lett 8 (2006) 3681
44. Raposo M.M.M., Sousa A.M.R.C., Kirsch G., Ferreira F., Belsley M., Gomes E.M., and Fonseca A.M.C. Tetrahedron 61 (2005) 11991
45. Raposo M.M.M., Sousa A.M.R.C., Fonseca A.M.C., and Kirsch G. Tetrahedron 61 (2005) 8249
46. Batista R.M.F., Costa S.P.G., Malheiro E.L., Belsley M., and Raposo M.M.M. Tetrahedron 63 (2007) 4258
47. Costa S.P.G., Batista R.M.F., Cardoso P., Belsley M., and Raposo M.M.M. Eur J Org Chem (2006) 3938
48. Yen M.S., and Wang I.J. Dyes Pigments 62 (2004) 173
49. Leclerc N., Galmiche L., and Attias A.-J. Tetrahedron Lett 44 (2003) 5883
50. Gong W., Li Q.Q., Li Z., Lu C.G., Zhu J., Li S.Y., et al. J Phys Chem B 110 (2006) 10241
51. Zhang C., Ren A.S., Wang F., and Dalton L.R. Polym Prepr 40 (1999) 49
52. Denta V., Levy Y., Dumont M., Robin P., and Chastaing E. Opt Commun 69 (1989) 379
53. Ma H., Liu S., Luo J.D., Suresh S., Liu L., Kang S., et al. Adv Funct Mater 12 (2002) 565
54. Robinson B.H., and Dalton L.R. J Phys Chem A 104 (2000) 4785
55. Harper A.W., Sun S., Dalton L.R., Garner S.M., Chen A., Kalluri S., Steier W.H., and Robinson B.H. J Opt Soc Am B 15 (1998) 329
56. Coleman G.H., and David C. Org Synth Coll vol. 2 (1943) 179
57. He M.Q., Zhu J.S., Harper A.W., Sun S.S., Dalton L.R., Garner S.M., et al. ACS Symp Ser (Org Thin Film) 695 (1998) 258