Synthesis of linear monodisperse vinylene-linked phenothiazine oligomers

Tetrahedron Letters

Volumn 48, Issue 43, 2007, Pages 7582-7585

  Qiu, Xianping ^a   Lu, Ran ^a   Zhou, Huipeng ^a   Zhang, Xiaofei ^a   Xu, Tinghua ^a   Liu, Xingliang ^a   Zhao, Yingying ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Heck reaction; Oligomers; Phenothiazine; Wittig reaction

Indexed keywords

OLIGOMER; PHENOTHIAZINE; UNCLASSIFIED DRUG; VINYLENE;

ARTICLE; CHEMICAL STRUCTURE; FLUORESCENCE; WITTIG REACTION;

EID: 34548824808     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.002     Document Type: Article

References (55)

1. Tour J.M. Chem. Rev. 96 (1996) 537-554
2. Martin R.E., and Diederich F. Angew. Chem., Int. Ed. 38 (1999) 1350-1377
3. Schwab P.F.H., Smith J.R., and Michl J. Chem. Rev. 105 (2005) 1197-1280
4. Roncali J. Acc. Chem. Res. 33 (2000) 147-156
5. Van Hutten P.F., Wideman J., Meetsma A., and Hadziioannou G. J. Am. Chem. Soc. 121 (1999) 5910-5918
6. Katz H.E. J. Mater. Chem. 7 (1997) 369-376
7. Schon J.H., Dodabalapur A., Kloc C., and Batlogg B. Science 290 (2000) 963-965
8. Garnier F., Yassar A., Hajlaoui R., Horowitz G., Deloffre F., Servet B., Ries S., and Alnot P. J. Am. Chem. Soc. 115 (1993) 8716-8721
9. de la Cruz J.L.D., Hahn U., and Nierengarten J.F. Tetrahedron Lett. 47 (2006) 3715-3718
10. Eckert J.F., Nicoud J.F., Nierengarten J.F., Liu S.G., Echegoyen L., Barigelletti F., Armaroli N., Ouali L., Krasnikov V., and Hadziioannou G. J. Am. Chem. Soc. 122 (2000) 7467-7479
11. Frere P., Raimundo J.M., Blanchard P., Delaunay J., Richomme P., Sauvajol J.L., Orduna J., Garin J., and Roncali J. J. Org. Chem. 68 (2003) 7254-7265
12. In: Müllen K., and Wegner G. (Eds). Electronic Materials: The oligomer approach (1997), Wiley-VCH, Weinheim
13. Elandaloussi E.H., Frère P., Richomme P., Orduna J., Garin J., and Roncali J. J. Am. Chem. Soc. 119 (1997) 10774-10784
14. Jestin I., Frère P., Blanchard P., and Roncali J. Angew. Chem., Int. Ed. 37 (1998) 942-945
15. Jestin I., Frère P., Mercier N., Levillain E., Stievenard D., and Roncali J. J. Am. Chem. Soc. 120 (1998) 8150-8158
16. Xu T.H., Lu R., Jin M., Qiu X.P., Xue P.C., Bao C.Y., and Zhao Y.Y. Tetrahedron Lett. 46 (2005) 6883-6886
17. Xu T.H., Lu R., Liu X.L., Zheng X.Q., Qiu X.P., and Zhao Y.Y. Org. Lett. 9 (2007) 797-800
18. Xu T.H., Lu R., Qiu X.P., Liu X.L., Xue P.C., Tan C.H., Bao C.Y., and Zhao Y.Y. Eur. J. Org. Chem. (2006) 4014-4020
19. Zhao Z.J., Zhao Y.X., Lu P., and Tian W.J. J. Phys. Chem. C 111 (2007) 6883-6888
20. Li B.S., Li J., Fu Y.Q., and Bo Z.S. J. Am. Chem. Soc. 126 (2004) 3430-3431
21. Liu Q., Liu W.M., Yao B., Tian H.K., Xie Z.Y., Geng Y.H., and Wang F.S. Macromolecules 40 (2007) 1851-1857
22. Lee S.H., Nakamura T., and Tsutsui T. Org. Lett. 3 (2001) 2005-2007
23. Kanibolotsky A.L., Berridge R., Skabara P.J., Perepichka I.F., Bradley D.D.C., and Koeberg M. J. Am. Chem. Soc. 126 (2004) 13695-13702
24. Wang S.J., Oldham W.J., Hudack R.A., and Bazan G.C. J. Am. Chem. Soc. 122 (2000) 5695-5709
25. Gomez-Escalonilla M.J., Langa F., Rueff J.M., Oswald L., and Nierengarten J.F. Tetrahedron Lett. 43 (2002) 7507-7511
26. Louie J., and Hartwig J.F. Macromolecules 31 (1998) 6737-6739
27. Lehn J.M. Angew. Chem., Int. Ed. Engl. 27 (1988) 89-112
28. Roncali J. Chem. Rev. 97 (1997) 173-206
29. Baigent D.R., Hamer P.J., Friend R.H., Moratti S.C., and Holmes A.B. Synth. Met. 71 (1995) 2175
30. Okamoto T., Kuratsu M., Kozaki M., Hirotsu K., Ichimura A., Matsushita T., and Okada K. Org. Lett. 6 (2004) 3493-3496
31. Krämer C.S., Zeitler K., and Müller T.J.J. Tetrahedron lett. 42 (2001) 8619-8624
32. Krämer C.S., and Müller T.J.J. Eur. J. Org. Chem. 18 (2003) 3534-3548
33. Krämer C.S., Zeitler K., and Müller T.J.J. Org. Lett. 2 (2000) 3723-3726
34. Kong X.X., Kulkarni A.P., and Jenekhe S.A. Macromolecules 36 (2003) 8992-8999
35. Wu T.Y., and Chen Y. J. Polym. Sci., Part A: Chem. 40 (2002) 4452-4462
36. Hwang D.H., Park M.J., and Lee C.H. Synth. Met. 152 (2005) 205-208
37. Sailer M., Rominger F., and Müller T.J.J. J. Organomet. Chem. 691 (2006) 299-308
38. Zhang X.H., Choi S.H., Choi D.H., and Ahn K.H. Tetrahedron Lett. 46 (2005) 5273-5276
39. Cho N.S., Park J.H., Lee S.K., Lee J., Shim H.K., Park M.J., Hwang D.H., and Jung B.J. Macromolecules 39 (2006) 177-183
40. Sun X.B., Liu Y.Q., Xu X.J., Yang C.H., Yu G., Chen S.Y., Zhao Z.H., Qiu W.F., Li Y.F., and Zhu D.B. J. Phys. Chem. B 109 (2005) 10786-10792
41. Bucci N., and Müller T.J.J. Tetrahedron Lett. 47 (2006) 8323-8327
42. Bucci N., and Müller T.J.J. Tetrahedron Lett. 47 (2006) 8329-8332
43. Lai R.Y., Fabrizio E.F., Lu L.D., Jenekhe S.A., and Bard A.J. J. Am. Chem. Soc. 123 (2001) 9112-9118
44. Lai R.Y., Kong X.X., Jenekhe S.A., and Bard A.J. J. Am. Chem. Soc. 125 (2003) 12631-12639
45. Kulkarni A.P., Wu P.T., Kwon T.W., and Jenekhe S.A. J. Phys. Chem. B 109 (2005) 19584-19594
46. Kim G.W., Cho M.J., Yu Y.J., Kim Z.H., Jin J.I., Kim D.Y., and Choi D.H. Chem. Mater. 19 (2007) 42-50
47. Hwang D.H., Kim S.K., Park M.J., Lee J.H., Koo B.W., Kang I.N., Kim S.H., and Zyung T. Chem. Mater. 16 (2004) 1298-1303
48. Fungo F., Jenekhe S.A., and Bard A.J. Chem. Mater. 15 (2003) 1264-1272
49. Mizoroki T., Mori K., and Ozaki A. Bull. Chem. Soc. Jpn. 44 (1971) 581
50. Heck H.F., and Nolley J.P. J. Org. Chem. 37 (1972) 2320-2322
51. Horner L., Hoffmann H.G., and Klahre G. Chem. Ber. 92 (1959) 2499
52. 6: C, 78.68; H, 7.60; N, 4.17; S, 9.55. Found: C, 78.77; H, 7.72; N, 4.13. MS, m/z: calcd: 2015.0, found: 2014.3.
53. Wang Q., and Yu L.P. J. Am. Chem. Soc. 122 (2000) 11806-11811
54. Mikroyannidis J.A. Chem. Mater. 15 (2003) 1865-1871
55. He F., Xia H., Tang S., Duan Y., Zeng M., Liu L.L., Li M., Zhang H.Q., Yang B., Ma Y.G., Liu S.Y., and Shen J.C. J. Mater. Chem. 14 (2004) 2735-2740