氮-苯基吡啶-2-胺基與當量數的醋酸鈀，在二氯甲烷為溶劑， 65-70℃下反應4小時，即可得高產率的鈀環化合物 53，得
到的鈀環化合物與芳香基三氟硼酸鉀在1,4-二氧六環為溶劑，
140℃下反應24小時，進行二次碳-氫鍵的活化，可得到產物咔唑 55a-55m。取咔唑衍生物 55a與三氯化銥進行錯合，可得到二聚體錯合物，再與2-甲酸吡啶進行配位基的交換，即可得銥
錯合物，可進一步應用於有機發光二極體材料。

N-phenylpyridin-2-amine , treated with stochiometric amount of palladium(II) acetate in dichloromethane at 65-70℃ for 4 h, to give high yield palladacycle 53. The reaction of palladacycle 53 with potassium aryltrifluoroborates in 1,4-dioxane at 140℃ for 24 h, could give a variety of N-(2-pyridinyl)carbazoles 55a-55m
via sequential C-H bond activation. Carbazole derivative 55a reacted with irdium chloride gave iridium dimer, which followed by addition of picolinic acid via ligand exchange will form iridium complexes, which can further be utilized as OLEDs materials.

目錄
章節 頁次
第一章、緒論
1.1 前言
………...………………………………………………………1
1.1.1 Carbazole之簡介
…………………………………………………..……………1
1.1.2 Carbazole之合成
……………………………………………..........……………5
1.2 Palladium-Catalyzed Cross-Coupling
…………………………….…………………………………10
1.3 Pd-Catalyzed Directed C-H Functionalization
…….…...................…………………………………………14
1.4 Carbazole之應用
……………………………………………….....……………19

第二章、研究動機
……………………………………………………...…………23

第三章、結果與討論
3.1 製備方法
…………………………………………………..............……26
3.2.1 氧化試劑之測試
.............................................................................……………31
3.2.2 反應溶劑之測試
.............................................................................……………32
3.2.3 反應機制之探討
.............................................................................……………33
3.2.4 環化反應之測試
……………………………………………….....……………35
3.2.5 不同芳香基三氟硼酸鉀鹽試劑對反應結果之影響
.....................…………………………………………………36
3.2.6 對-苯二酮對反應的影響
………………………………………....……………………40
3.3.1銥金屬錯合物合成方法
………………………………………...………………………41
3.3.2 UV-Vis 吸收光譜
…………………………………………...…..………………43
3.3.3 螢光放射光譜
…………………………………………………...……………45
3.4 結論
……………………………………………………………..…46

第四章、化合物的製備方法
4.1 儀器部分
………………………………………………………….……47
4.2 實驗部分
………………………………………………………….……48
方法 A. 化合物 N-phenylpyridin-2-amine (52)
…………….…………………………………………………48
方法 B. 化合物 Palladacycle (53)
…………………………………..……………………………49
方法 C. 化合物 9-(pyridin-2-yl)-9H-carbazole (55a)
........................………………………………………………49
化合物 3-Nitro-9-(pyridin-2-yl)-9H-carbazole (55c)
...........................………………………………………………51
化合物 9-(Pyridin-2-yl)-9H-carbazole-2-carbaldehyde (55d)
.............………………………………………………………52
化合物 2-tert-Butyl-9-(pyridin-2-yl)-9H-carbazole (55i)
....................…………………………………………………53
化合物 2-Methyl-9-(pyridin-2-yl)-9H-carbazole (55j)
………………………………………………………………54
化合物 2-Methoxy-9-(pyridin-2-yl)-9H-carbazole (55k)
…………….…………………………………………………55
化合物 5-(Pyridin-2-yl)phenanthridin-6(5H)-one (55l)
........................………………………………………………57
化合物 (cpy)2Ir(pico) (64)
.....................................................................…………………58
化合物 N-(biphenyl-2-yl) pyridin-2-amine (65)
……………………....………………………………………59

化合物 Palladacycle (53) 晶體結構數據
……..……………………..…………………………………61
化合物 9-(pyridin-2-yl)-9H-carbazole (55a) 晶體結構數據
..............………………………………………………………72

第五章、參考文獻
………………………………………………………………78

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