在本論文中 ,我們合成一些具有螢光性質的不同取代的衍生物 .
一開始 ,我們利用吲哚為起始物 , 在第三位置甲醯化 ,利用相轉移觸媒在氮上位置進行烷化 , 接著與不同取代苯醯進行縮合反應 , 最後以醛類半卡方式氧化成1 ,3 ,4-二唑環

以醛類半卡方式使用過錳酸鉀在丙酮溶液中氧化成1 ,3 ,4-二唑環衍生物是十分有效的 ,產率比一般已知的方法要來得高 .

我們希望 ,透過這些研究 ,能提供一個不錯方法來合成一些具有1 ,3 ,4-二唑環的吲哚衍生物 ,能應用在有機發光體上

In this paper , we have synthesized a variety of substituted indoles derivaties with fluorescent properties
first , we use indole as a starting material , formylation in third site of 1H-indole , the N-alkylation of 3-formyl-indole is achieved using phase transfer catalysis , the condensation reactions of 3-formyl 1H-indole and different substituted aroylhydrazines , finally oxidize aldehyde semicarbazones to 1, 3, 4 –oxadiazole ring .

The oxidation of aldehyde semicarbazones with potassium permanganate (Ⅶ) in acetone was effected , afford 1, 3, 4 –oxadiazole derivatives , often in higher yields than the known methods .

we hope that , through these studies , can be provided a right way to synthesize indoles derivaties include 1, 3, 4 –oxadiazole ring., applies in OLED .

參考文獻
1.Loupy, J . Sansoulet , E . Diez-Barra and J . R . Carrillo , Synth . Commun. ,1991,21 ,1465
2.J. K. Kim. , S. I. Hong , H. N. Cho , D. Y. Kim , C. Y. Kim , Polymer. Bulletin ,1997, 38 , 169
3.S. Y. Song , M. S. Jang , H. K. Shim , D. H. Hwang and T. Zyung , Macromolecules , 1999 , 32 ,1482
4. S. Maruyama , Y. Zhang , T. Wada and H. Sasabe , J. Chem. Soc. Perkin.Trans. 1 , 1999 , 1 , 41
5. S. Maruyama , H. Hokari , T. Wada , H. Sasabe , Synthesis ,2001 ,12, 1794
6. J. Barry , G. Bram , G. Decodts , A. Loupy , P. Pigeon et and J. Sansoulet , Tetrahedron Lett. , 1982 , 23 , 51, 5407
7. D. Wim and H. Alfred , J. Org. Chem. , 1991 , 56 , 896
8. R. Stolle , J. Prakt Chem. , 1903 , 68 , 130
9. F. Maggio , G. Werber and G. Lombardo , Ann. Chim. , 1960 , 50 , 491
10. S. A. Dausse , Chem. Abstr. , 1966 , 64 , 5106
11. G. Werber and F. Maggio , Ann. Chim. , 1952 , 42 , 747
12. M. S. Gibson , Tetrahedron , 1962 , 18 , 1377
13. H. Najer , J. Menin and J. F. Giudicelli , C r hebd seanc Acad Sci. Paris. , 1964 , 258 , 4579
14. R. Stolle and E. Mnsch , J. Prakt. Chem.1904 , 70 , 393
15. G. Mazzone , G. Puglisi , G. Marchetta and A. Corsaro , J.Heterocycl. Chem. , 1984 , 21 , 181
16. T. H. Nguyen , R. Milcent and G. Barbier , J. Heterocyclic Chem. , 1985 , 22 , 1383
17. J. D. Bower and F. P. Doyle , J. Chem. Soc. ,1957 , 727
18. W. A. F. Gladstone , J. B. Aylward and R. O. C. Norman , J. Chem.Soc.1969 , 2587
19. S. A. Rekkas , N. A. Rodios and N. E. Alexandrou , Communications , 411
20. S. P. Hiremath , Indian J. Chem. Sect. B , 1978 , 16B , 789
21. F. A. A. E1-Marich , H. A.Saad , H. A. Allimony and R. M. Abdel- Rahman , Indian J. Chem.Sect.B , 2000 , 39 , 36
22. Chiba , Toshiro , Okimoto , Mitsuhiro , J. Org. Chem. , 1992 , 57 , 5 , 1375
23. P. S. N. Reddy , P. P. Reddy , Indian J. Chem. Sect. B , 1987 , 26B , 890
24. O. A. Salman and H. G. Drickamer , J.Chem. Phys. , 1982 , 77 , 3329
25. K. D. Ashby , K. Das and J. W. Petrich , Anal. Chem. , 1997 , 69 , 1925
26. P. R. Callis , J. Chem. Phys. , 1991 , 95 , 6 , 4230
27. L. S. Andres and B. O. Roos , J. Am. Chem. Soc. , 1996 , 118 , 185
28. R. N. Goyal , N. Kumar and N. K. Singhal , Bioelectro. and Bioenerg. , 1998 , 45 , 47
29. C.Adachi , T. Tsutsui and S. Saito , Appl. Phy. Lett. 1989 ,55 ,1489
30. Yuji Hamada , Chihaya Adachi , Tesuo Tsusui and Shogo Saito , Jpn . J. Appl. Phys. 1992 , 31 , 1812
31. D. O’Bradley and T. Tsutsui , J. Appl. Phys. 1997 , 82 , 2662
32. K.Kawate , K. –I. Ohkura , M. Yamazaki , M. Kuroda and O. Nabeta , Proc. SPIE Int.Soc.Opt. Eng. 1994, 2174 ,200
33. H. Ueda , T. Kitahora , K.Furukawa and Y. Terasaka , Synth. Met. ,1997,91,257
34.C. Zhang , H. von Seggern , K. Pakbaz , B. Kraabel , H.W.Schmidt , and A. Heeger , J. Synth. Met. , 1994 ,62 , 35
35. B.Hu , Z. Yang and F. E.Karasz , J. Appl. Phys. , 1994 ,76 , 2419
36. Z. Zhu ; J. S. Moore. J. Org. Chem. , 2000 , 65 , 116
37. J. A. Joule , Heterocycl. Chem. , 1984 , 35 , 83
38. 柯畢嘉, 林建村 , 化學, 2002. , 60 , 1 , 85
39. Yeh M. Y. , J. H. Tien , Y. L. Haung , H. M. Chen , J. Chin. Chem. Soc., 1983 , 30, 29
40. C. Hosokawa , Us 5 ,1992 ,142 ,343
41. S. Pfeiffer , H. –H. Horhold and H. Boerner , Proc. SPIE Int. Soc Opt.Eng. 1998 ,3476 ,258
42. S . Dirr , S. Wiese , H. –H. Johannes , D. Ammermann and W. Kowalsky , Synth. Met. 1997 ,91, 53
43. P. Jolinat , R. Clergereaux , J. Farenc and P. Destruel , J. Phys. D : Appl. Phys. , 1998 , 31 ,1257
44. J. Kido , M. Kimura and K. Nagai , Chem. Lett. , 1996 , 47
45. I. K. Yakushchenko , M. G. Kaplunov , O. N. Efimov and S. N. Shamaer , Phys. Chem. Chem. Phys. , 1999 , 1 , 1783
46. J. Kido , M. Kimura and K. Nagai , Scinece , 1995 , 267 , 1332
47. Y. –G. Ma , W. –H. Chan , X. –M. Zhou and C.-M. Che, New J. Chem. ,1999 , 263
48. 謝昇穎 ,國立成功大學碩士論文,2001
49. M.Pope , H. P. Kallman and P. Mangnante , J. Chem. Phys. , 1963 , 38, 2042
50. C. Wang , G. Y. Jung , Y. Hua and C. Pearson , Chem. Mater. , 2001 , 13 ,1167
51. G. Y. Jung , C. Wang , C. Person , M. R. Bryce , I. D. W. Samuel and M. C. Petty , Proc. SPIE , 2001, 4105 ,307
52. B. Hu , Z. Yang and F. E. Karasz , J. Appl. Phys. , 1994 ,76 , 2419
53. G.Wang , C. Yuan , H. Wu and Y. Wei , J. Appl. Phys. , 1995 , 78 , 2679
54. Y. Z.Wang and Epstein , A. J. Acc.Chem. Res. , 1999, 32 , 217