Habenicht Stefanie H, Siegmann Michael, Kupfer Stephan, Kübel Joachim, Weiß Dieter, Cherek Doreen, Möller Uwe, Dietzek Benjamin, Gräfe Stefanie, Beckert Rainer
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University, Humboldtstr. 10, 07743 Jena, Germany.
Methods Appl Fluoresc. 2015 Jun 18;3(2):025005. doi: 10.1088/2050-6120/3/2/025005.
Reported is a study on the influence of regioisomerism on the photophysical properties in 4-hydroxy-1,3-thiazole-based push-pull-chromophores/fluorophores to evaluate the molecular structure-property relationship as a basic foundation for future design strategies concerning this class of dyes. Surprisingly, the nitro groups used as acceptors do not act as a fluorescence quencher, instead the derivatives synthesized exhibit quantum yields of 37-40%. Two 4-ethoxy-1,3-thiazole derivatives which differ only in the positioning of their electron donating (methoxy) and electron withdrawing (nitro) groups have been synthesized and examined in terms of their photophysical properties, i.e. UV/Vis absorption and fluorescence emission spectra. Additionally, quantum chemical calculations have been performed to unravel the underlying fundamental transitions and to explain the experimental results.
报道了一项关于区域异构对基于4-羟基-1,3-噻唑的推拉型发色团/荧光团光物理性质影响的研究，以评估分子结构-性质关系，作为此类染料未来设计策略的基础。令人惊讶的是，用作受体的硝基并不充当荧光猝灭剂，相反，合成的衍生物表现出37-40%的量子产率。合成了两种仅在供电子（甲氧基）和吸电子（硝基）基团位置上不同的4-乙氧基-1,3-噻唑衍生物，并对其光物理性质进行了研究，即紫外/可见吸收光谱和荧光发射光谱。此外，还进行了量子化学计算，以揭示潜在的基本跃迁并解释实验结果。
