| 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 |
| 相關次數: | 點閱:55 下載:5 |
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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.
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