Maeda Chihiro, Todaka Takumi, Ueda Tomomi, Ema Tadashi
Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama, 700-8530, Japan.
Chemistry. 2016 May 23;22(22):7508-13. doi: 10.1002/chem.201505150. Epub 2016 Apr 13.
Several carbazole-based boron dipyrromethene (BODIPY) dyes were synthesized by organometallic approaches. Thiazole, benzothiazole, imidazole, benzimidazole, triazole, and indolone substituents were introduced at the 1-position of the carbazole moiety, and boron complexation of each dipyrrin generated the corresponding compounds 1, 2 a, and 3-6. The properties of these products were investigated by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X-ray crystallography, and DFT calculations. These compounds exhibited large Stokes shifts, and compounds 1, 2 a, and 3-5 fluoresced both in solution and in the solid state. Complex 2 a showed the highest fluorescence quantum yield (ΦF ) in the solid state, therefore boron complexes of the carbazole-benzothiazole hybrids 2 b-f, which had several different substituents, were prepared and the effects of the substituents on the photophysical properties of the compounds were examined. The fluorescence properties showed good correlation with the results of crystal-packing analyses, and the dyes exhibited color-tunable solid-state fluorescence.
通过有机金属方法合成了几种基于咔唑的硼二吡咯亚甲基（BODIPY）染料。在咔唑部分的1位引入了噻唑、苯并噻唑、咪唑、苯并咪唑、三唑和吲哚酮取代基，每个二吡咯的硼络合反应生成了相应的化合物1、2a以及3 - 6。通过紫外/可见光谱和荧光光谱、循环伏安法、X射线晶体学以及密度泛函理论（DFT）计算对这些产物的性质进行了研究。这些化合物表现出较大的斯托克斯位移，化合物1、2a以及3 - 5在溶液和固态中均能发出荧光。配合物2a在固态中表现出最高的荧光量子产率（ΦF），因此制备了具有几种不同取代基的咔唑 - 苯并噻唑杂化物2b - f的硼配合物，并研究了取代基对化合物光物理性质的影响。荧光性质与晶体堆积分析结果显示出良好的相关性，并且这些染料表现出颜色可调的固态荧光。
