臺灣博碩士論文加值系統

本研究所合成出一系列新的發光分子，以咵唑作為一個電子傳遞單元和咔唑作為一個電洞傳遞單元的苯并吡啶化合物2QB-C6-C6、1QB-C6-C6、2QB-C6-OX、1QB-C6-OX，一開始以3-乙炔基-9-己基-咔唑2為原料，和9-己基-3-碘基-咔唑3及2-(4-三級丁苯基)-5-(4-碘苯基)-[1,3,4] 咵唑4用鈀催化生成雙(9-乙基-3-咔唑基)乙炔5和3-{4-[5-(4-三級丁苯基)-2[1,3,4] 咵唑基]-苯乙炔基}-9-己基-咔唑6，其產率約為50%。
化合物5、6以高錳酸鉀及緩衝丙酮溶液中，可得到1,2-雙(9-己基-3-咔唑基)-乙烷-1,2-雙酮7及1-{4-[5-(4-三級丁苯基)-2-[1,3,4] 咵唑基}-2-(9-己基-3-咔唑基)-乙烷-1,2-雙酮8，和1,2,4,5-四胺基苯1及3,4,3’,4’-四胺基聯苯1’接上即可完成。含1,3,4-咵唑之化合物9、10，是以原料1,2-雙{4-[5-(4-三級丁苯基)-2-[1,3,4] 咵唑基]-苯基}-乙烷-1,2-雙酮11。含苯并吡啶化合物的螢光波長落在綠光區，而雙苯并吡啶化合物落在藍-綠光區，其Stokes shift大部分少於50nm，顯示了激發峰及吸收峰重疊的部分過多。
六(9-烷基-3-咔唑基)苯12(n=5~10)是由雙(9-烷基-3-咔唑基)乙炔，經觸媒Co2(CO)8環化的結果，其化合物12之衍生物中(n=5,9, 10)由POM觀察，顯示了具有互變性圓柱液晶相，其餘的(n=7,8)皆呈結晶狀。
本研究所合成的化合物皆經由NMR、Mass及飛行質譜儀鑑定其結構。

The synthetic pathway to a series of new emitter molecules having an oxadiazole group as an electron transport unit and a carbazole group as hole transport unit based on quinoxzline 1QB-C6-C6，2QB-C6-C6 and 1QB-C6-OX，2QB-C6-OX start with the palladium-catalyzed coupling or cross coupling of the 3-Ethynyl-9-hexyl-carbazole 2 with 9-Hexyl-3-iodocarbazole 3 and 2-(4-tert-butylphenyl)-5-(4-iodophenyl)-[1,3,4]oxadi-azole 4 to bis[9-hexyl-carbazole-3-yl]ethyne 5 and 3-{4-[5-(4-tert-butylphenyl)-[1,3,4]oxadiazole-2-yl]-phenylethyn-yl}-9-hexyl-carbazole 6，respectively which are obtained in about 50% yield。
Alkyne 5 and 6 were treated with permanganatein neutral，buffered aqueous acetone，a 85%yield of new diketones 1,2-bis-(9-hexylcarbazole-3-yl)-ethane-1,2-dione 7 and 1-{4-[5-(4-tert-butylphenyl)-[1,3,4]oxadiazole-2-yl]-phenyl}-2-(9-hexylcarbazole-2-yl)-ethane-1,2-dione 8，were obtained。Subsequent condensation with benzene-1,2,4,5-tetraamine 1 and biphenyl-3,4,3’,4’-tetraamine 1’ led to。 The 1,3,4-Oxadia-zole-containing molecules 9 and 10 with a quinoxaline or a biquinoxaline core were prepared by an analogous procedure starting from 1,2-bis-{4-[5-(4-tert-butylphenyl)-[1,3,4] oxadiazole-2-yl]-phenyl}-ethane-1,2-dione 11。All compounds were characterized by IR and NMR and Mass spectroscopy or MALDI-TOF analysis。
Hexa(9-alkylcarbazole-3-yl)benzenes 12(with n=5~10)，were prepared by Co2(CO)8 catalyzed cyclotrimerization of the corresponding Bis(9-alkylcarbazole-3-yl)ethyne monomers 12。 The derivatives 12 (n=7,8) are crystalline。 The deri-vatives 12 (n=5,9,10) display an enantiotropic columnar mesophase observed by polarized optical microscopy。

中文摘要
英文摘要
致謝
目錄
List of Scheme
List of Figure
List of Table
第一章 前言
第二章 實驗 1
2-1 藥品 4
2-2 實驗儀器與測試方法 4
2-3 合成方法 11
第三章 結果
3-1 單體之合成與鑑定 28
3-2 液晶相之鑑定與物性之探討 69
第四章 討論 95
第五章 總結 98
參考資料 99

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