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標題: | 具推拉電子基之苯炔烯共軛系統合成與電致化學發光性質之研究 Studies on The Synthesis and Electrochemiluminecent Properties of Donor-Acceptor Substituted PhenyleneEthynyleneVinylene Conjugated Systems |
作者: | Chi-Wei Hsu 許哲維 |
指導教授: | 楊吉水 |
關鍵字: | 電致化學發光,推拉電子基,苯乙烯吡,啶, ECL,donor-acceptor,stilbazole, |
出版年 : | 2006 |
學位: | 碩士 |
摘要: | 本論文中,我們利用Sonogashira 偶合反應合成兩系列具有
推拉電子共軛系統的苯炔烯類化合物,分別為1-phenylethynyl- 4-(trans-4-pyridylethenyl)benzene系列(1)及1-phenylethynyl-4-(trans- 2-pyridylethenyl)benzene系列(2),並研究其光物理性質、電化學特性及電致化學發光性質(Electrogenerated ChemiLuminescence; ECL)。 此二系列化合物的UV-Vis吸收光譜、螢光放光光譜與電化學量測及電致化學發光實驗,均在乙腈溶液下量測。化合物1與2的UV-Vis吸收峰分布在335 nm到369 nm之間,螢光放光峰則分布在390 nm到550 nm之間,而其分布隨著分子極性的增加(即由a到e)而有紅位移的現象產生。化合物1和2中以b、c、d取代者,具有較好的螢光量子產率(ΦFlu),其ΦFlu值均高於0.5,尤其又以2d為最高,為0.77。 在電致化學發光性質的研究方面,我們提供化合物溶液足夠的氧化及還原電位,再以ECL裝置分別記錄除氧條件下的ECL光譜。我們發現ECL光譜的分布集中在440 nm 到470 nm之間,只有化合物2e紅位移至540 nm。這種現象顯示了ECL對於分子極性改變的不敏感,我們認為在ECL的反應過程中涉及了二聚體(excited dimer)的發生。 We have synthesized two series of donor-acceptor substituted pi-conjugated phenylvinylene/phenylethynylene systems by the Sonogashira coupling reactions : namely, the 1-phenylethynyl-4-(trans-4- pyridylethenyl)benzenes, (1), and the 1-phenylethynyl-4-(trans-2- pyridylethenyl)benzenes, (2). We report, in this dissertation, their synthesis, photophysical, electrochemical and Electrogenerated ChemiLuminescence(ECL) properties. All the measurements of UV-Vis absorption, fluorescence emission, electrochemistry, and ECL for 1 and 2 were carried out in acetonitrile solutions. The UV-Vis absorption maxima of 1 and 2 are between 335 and 369 nm, and their fluorescence emission maxima between 390 and 550 nm. Those with stronger donors (i.e., a<b<c<d<e) possess longer wavelengths of both the absorption and fluorescence maxima. The fluorescence spectra are more sensitive than the UV-Vis spectra to the nature of the donor group. All these compounds have high fluorescence quantum yield(ΦFlu), and amound them, 2d has the highest value(ΦFlu = 0.77). The ECL of 1 and 2 in outgassed acetonitrile solutions were measured under a condition in which the substrates can be reduced and oxidized. The ECL maxima are all in the range of 440-470 nm, except for 2e located at 540 nm. These observation indicate that the ECL of 1 and 2 are insensitive to position and nature of substituent. This can be attributed to the ECL emission from excited dimmers. |
URI: | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/23991 |
全文授權: | 未授權 |
顯示於系所單位: | 化學系 |
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