具推拉電子基之香豆素及苯并噻唑炔類衍生物之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 Arylethynyl Coumarins and Benzothiazoles

黃莘豪(Hsin-Hau Huang)

指導教授 ： 楊吉水

國立臺灣大學/理學院/化學研究所/碩士(2006年)

https://doi.org/10.6342/NTU.2006.10099

摘要

本篇論文主要是討論D-π-A(Donor-π-Acceptor)系統的電致化學發光性質(ECL)，其中D為-H(H)、-Me (M)、-OMe (OM)、-OiPr (OP)或-NMe2 (DMA)，π為苯乙炔或二苯乙炔，A為香豆素(coumarin)或苯并噻唑(benzathiazole)。我們希望探討位置異構物對D-π-A系統ECL性質的影響。
以香豆素為電子受體的化合物為5-香豆素(5Cs)及7-香豆素(7Cs)
系列。除了5C-DMA和7C-DMA之外，其餘化合物隨著推電子基增強
(H

關鍵字

電致化學發光 ； 香豆素 ； 苯并噻唑

並列摘要

In this dissertation, we report the photophysical, electrochemical, and electrogenerated chemiluminescent properties of a series of donor-p-acceptor (D-p-A) systems, where D is H(H), Me(M), OMe(OM), OiPr(OP) or NMe2(DMA),p is phenylacetylene or diphenylacetylene, and A is coumarin or benzathiazole. The position-dependent substituent effects on the ECL behavior of these D-p-A systems are also reported.
The investigated coumarin systems are 5- and 7-substitued coumarins, which are referred to as 5Cs and 7Cs, respectively. The fluorescence of 5Cs and 7Cs are at longer wavelengths for those with stronger donors(i.e., H < M < OM < OP < DMA). Except for 5C- DMA and 7C-DMA that possess low fluorescene quantum yields (<0.01), 5Cs and 7Cs display stronger fluorescence for those with stronger donors. ECL signals (λmax = 460- 500 nm) can be observed for 5Cs and 7Cs under aerated conditions but not under outgassed solutions.
Three benzathiazole systems (BTs, m-BTPhs and p-BTPhs) were inwestigated herein.The dependence of fluorescence position and fluorescence quantum yield on the donor group for these benzathiazole systems resembles that for 5Cs and 7Cs. However, unlike the cases of 5Cs and 7Cs, BT-DMA, m-BTPhs and p-BTPhs display ECL signals in outgassed acetonitrile solution, and the ECL spectra can be correlated to the corresponding fluorescence spectra. Under aerated conditions, all these benzathiazole systems show ECL signals and maxima are all within the range of 460-500 nm, independent of the nature of substrates. The ECL mechanisms for both the coumarin and benzathiazole systems are also elucidated and discussed.

並列關鍵字

Electrochemiluminecent ； Coumarin ； Benzothiazole

參考文獻

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