A group of highly fluorescent 2,1,3-benzothiadiazole derivatives (BH0-BH3), including two fluorene derivatives (AB2 and C01) were synthesized and characterized. The electrochemical, spectroscopic, and electrogenerated chemiluminescence (ECL) properties of the compounds were determined. Benzothiadiazole derivatives BH1, BH2, and BH3 show reversible oxidation and reduction waves and produce strong green ECL in nonaqueous solutions. This ECL could be seen by the naked eye, even in a well lit room. The fluorene derivatives, C01 and AB2, also produce bright, easily observable ECL. Since the ECL spectra are at essentially the same wavelengths as the photoluminescence (PL) spectra, and the energies of the electron transfer reactions are greater than the singlet state energies, we propose direct formation of the excited singlet state during ion annihilation. BH0, which shows a quasi-reversible oxidation wave, only produced weak ECL via direct annihilation but gave strong ECL with benzoyl peroxide (BPO) as a coreactant. The ECL quantum efficiencies of the series, compared to that of 9,10-diphenylanthrace, was estimated to range from 0.05 to 7%. This series shows rare green photoluminescence (lambda(PL) = 490-556 nm) with a high PL quantum efficiency in solution (Phi = 5 to 90%).

中文翻译：

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高荧光苯并噻二唑和芴衍生物的绿色电生化学发光

合成并表征了一组高荧光2,1,3-苯并噻二唑衍生物（BH0-BH3），包括两种芴衍生物（AB2和CO1）。测定了化合物的电化学、光谱和电致化学发光 (ECL) 特性。苯并噻二唑衍生物 BH1、BH2 和 BH3 显示出可逆的氧化和还原波，并在非水溶液中产生强烈的绿色 ECL。即使在光线充足的房间里，也可以用肉眼看到这种 ECL。芴衍生物 CO1 和 AB2 也产生明亮、易于观察的 ECL。由于 ECL 光谱与光致发光 (PL) 光谱的波长基本相同，并且电子转移反应的能量大于单线态能量，我们建议在离子湮灭过程中直接形成激发单线态。BH0 显示准可逆氧化波，仅通过直接湮灭产生弱 ECL，但以过氧化苯甲酰 (BPO) 作为共反应物产生强 ECL。与 9,10-二苯蒽相比，该系列的 ECL 量子效率估计在 0.05% 到 7% 之间。该系列显示罕见的绿色光致发光（λ(PL) = 490-556 nm），在溶液中具有高 PL 量子效率（Phi = 5 至 90%）。