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研究生: 鄭育松
sung, cheng-yu
論文名稱: 合成苯并[k]荧蒽為基本結構的線性多并苯化合物
Synthesis of Benzo[k]fluoranthene-Based Linear Acenes
指導教授: 吳耀庭
Wu, Yao-Ting
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2008
畢業學年度: 96
語文別: 中文
論文頁數: 85
中文關鍵詞: 苯并[k]荧蒽線性多并苯
外文關鍵詞: benzo[k]fluoranthene, linear acenes
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  • 在醋酸鈀和醋酸銀的催化系統下,雙炔化合物(35, 44-45)可與碘化苯(27)和鄰二碘苯(30)反應而生成苯并[k]荧蒽為基本結構的線性多并苯化合物,已製備17種此類化合物(見表三與表四),產率為42%至93%。我們的合成方法有別於傳統的狄爾斯-阿爾德反應,可有效地導入官能基及芳香環系統。
    在雙炔化合物我們提供了數種可供製備:1,8-雙(苯乙炔基)萘(35a)、1,8-雙(苯乙炔基)苊(44a)、7,10-二甲基-3,4-雙(苯乙炔基)荧蒽(45a)與7,10-二甲基-3,4-雙(苯乙炔基)荧蒽-8,9-甲酸甲酯(45b)都效運用於合成苯并[k]荧蒽化合物。並且使用Sonogashira反應有助於雙炔化合物上苯乙炔基含官能基化,提供型式上變化。此外,芳香鹵化物參考文獻合成四種:1,2-二碘-4,5-二甲基苯(47b)、1,2-二碘-4,5-二甲氧基苯(47c)、2,3-二碘萘(49a)與1,2,4,5-四碘萘(51),加上商業提供碘化苯(27)共五種進行我們反應。
    數種化合物已進行光物理性質探討,期望化合物有好的發光性質,可做為發光材料。

    In the Pd(OAc)2 and AgOAc conditions, dialkyne compounds (35, 44-45)
    and o-diiodobenzene (30) synthesize 17 benzo[k]fluoranthene derivatives
    (table 3 and table 4), all reactions produce the products in 42% to 93%
    isolated yield. Our synthetic design is different from traditional methods that
    all use Diels-Alder reaction is easy to add electron donating groups 、electron
    withdrawing groups and aromatic system.
    We have offered several dialkyne compounds:1,8-bis(phenylethynyl)naphthalene(
    35a),1,8-bis(phenylethynyl)acenaphthalene(44a),7,10-dimethyl-3,4
    -bis(phenylethynyl)fluoranthene(45a), 7,10-dimethyl-3,4-bis(phenylethynyl)fluoranthene-
    8,9-dicarboxylate(45b). Sonogashira reaction is powerful to
    functionalize phenylacetylene on dialkyne, in addition, Table 2 summarizes
    the results of the reactions of various o-diiodoarenes, o-diiodoarenes can be
    easily prepared from either direct iodination of aromatic compounds with
    iodine and periodic acid.
    We measured representative compounds by UV−visible,photoluminescence
    spectra and hope it can be good materials in OLED.

    中文摘要.......................................................................................................Ⅰ 英文摘要.......................................................................................................Ⅱ 壹.前言...........................................................................................................1 貳. 結果與討論…………………………………………………..……….8 一. 起始物雙炔化合物與芳基鹵化物合成…………………..…………..9 (一) 合成雙炔化合物的前驅物……..………..………………….……….9 (二) 經Sonogashira 反應合成雙炔化合物……………………….12 (三) 芳基鹵化物合成……………………………………………………15 二. 雙炔化合物與芳基鹵化物的反應…………………………….……..18 三. X-Ray 單晶繞射儀結構鑑定………………………………...………..24 四.化合物光學性質探討………………………………………………….26 五.循環伏安法測定………………………………………...……………..35 參. 結論……………………………………….………………………...…37 肆. 實驗........................................................................................................39 伍. 參考文獻...............................................................................................61 陸. 附錄……………………………………………………………….…..64 核磁共振光譜圖…………………………………………………………...64

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