Studies on the Synthesis and Electrochemiluminecent Properties of Donor-Acceptor Substituted Arylethynyl Coumarins and Benzothiazoles
Date Issued
2006
Date
2006
Author(s)
Huang, Hsin-Hau
DOI
zh-TW
Abstract
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.
Subjects
電致化學發光
香豆素
苯并噻
唑
Electrochemiluminecent
Coumarin
Benzothiazole
Type
thesis
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