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研究生:徐國才
論文名稱:含口比咯共軛雜環化合物在二次非線性光學的應
論文名稱(外文):Synthetic Applications of Pyrrole-Containing Conjugated Heterocyclic Compounds in Second-Order Nonlinear Optics
指導教授:周善行周善行引用關係
學位類別:碩士
校院名稱:輔仁大學
系所名稱:化學學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:1998
畢業學年度:87
語文別:中文
論文頁數:104
中文關鍵詞:共軛雜環化合物二次非線性光學
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  近年來,非線性光學材料爆發了一股潮流,在遠距通訊、資訊傳輸、光電技術上有很
大的發展潛力,並也有商品化產品開發出來。有機非線性光學材料有許多的優點,如具有
較佳的二次非線性效應、較低的製作成本、合成上的彈性設計等。在發色團設計和合成上
,主要考慮的影響因素有:推-拉電子基的強度、共振主體和π-鍵橋的種類等。最近也發
現以雜環分子為共振主體的發色團具有相當高的非線性光學性質,所以本實現室這幾年致
力於研究雜環分子在二次非線性光學上的應用,然而截至目前為止含氮五員芳香雜環分子
的化合物口比咯(pyrrole),在二次非線性光學材料中,並無任何相關性的報導。
  所以本論文以含有口比咯(pyrrole)共軛雜環分子的二次非線性光學材料,進行合成
的研究。文獻報導,石風基是個好的拉電子基,也具有較佳的透光度,且更能在材料的合
成應用上具有彈性設計和官能基上的變化,因此本論文合成了以胺基為推電子基,石風基
為拉電子基,發色團中間π-鍵橋以碳-氮雙建為連結的口比咯(pyrrole)共軛雜環分子,
預期將具有好的二次非線性光學μβ值、好的透光性、熱穩定性等特性。
由所合成化合物1-4的UV-VIS吸收光譜,及化合物1-4利用溶劑色移效應
(Solvatochromism)可計算這些化合物的二次非線性光學μβ值,結果具有不錯的二次非
線性光學μβ值(μβ1064=90∼224×10-48esu, μβ0=37∼83×10-48esu),和良好
的透光性(在1, 4-dioxane中,最大吸收波長λmax=386∼402nm)。其中,2a化合物具
有相當不錯的非線性光學二次諧波產生(SHG),強度約為quartz的2.9倍。另外,化合物2b
可長成適合測試單晶繞射光譜(X-ray)的晶體,可惜發現是中心對稱堆積(P21/n)的化合物



  Recently, nonlinear optical(NLO) materials have attracted much attention. They have great potential especially in the field of long-distance communication, information transmittance and photoelectricity technology. There are some commercial products which are available now. Organic NLO materials have advantages as compared to inorganic materials, such as better second-order nonlinear properties, lower costs, greater ease for synthetic design. The major factors in designing these compounds include the strength of donor-acceptor group, the nature of the conjugated system and the π-bridge. It has recently been found that heterocyclic chromophores behave well as NLO materials, and thus we devote ourselves to the synthesis and applications of heterocyclic compounds in NLO. So far there are no reports on pyrrole-containing chromophores as second-order NLO materials.
  In this thesis my research focuses on pyrrole-containing chromo-phores as second-order NLO materials. It has been reported that the sulfone group is a good electron-withdrawing group with better transparency. It also provides flexibility in the synthetic process. Hence, a series of sulfone-substituted pyrrole chromophores bearing the π- bridge of C=N were designed. It is predicted that these compounds would possess good hyperpolarizability(μβ) and transparency, as well as high thermal stability.
  From the UV-VIS absorption spectra and solvatochromism of compounds 1-4, the hyperpolarizability can be calculated. The results show that these compounds high μβ values(μβ1064=90~224×10-48esu, μβ0=37~83×10-48esu) and good transparency(λmax=386nm~402nm in 1, 4-dioxane). Compound 2a has good nonlinear optical second harmonic generation(SHG) intensity, which is 2.9 times stronger than quartz. Compound 2b yields single crystals for measuring the X-ray diffraction, but unfortunately it is centrosymmetric with the P21/n space group.

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