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Color-Tunable Solid-State Fluorescence Emission from Carbazole-Based BODIPYs

机译:基于咔唑的BODIPY的颜色可调的固态荧光发射

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摘要

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, 2a, 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, 2a, and 3-5 fluoresced both in solution and in the solid state. Complex 2a showed the highest fluorescence quantum yield (Phi(F)) in the solid state, therefore boron complexes of the carbazole-benzothiazole hybrids 2b-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.
机译:通过有机金属方法合成了几种咔唑基硼二吡咯亚甲基(BODIPY)染料。在咔唑部分的1位上引入噻唑,苯并噻唑,咪唑,苯并咪唑,三唑和吲哚酮取代基,每个二吡啶的硼络合生成相应的化合物1、2a和3-6。通过UV / Vis和荧光光谱,循环伏安法,X射线晶体学和DFT计算研究了这些产品的性能。这些化合物表现出大的斯托克斯位移,并且化合物1、2a和3-5在溶液和固态均发出荧光。配合物2a在固态下显示出最高的荧光量子产率(Phi(F)),因此制备了具有几个不同取代基的咔唑-苯并噻唑杂化物2b-f的硼配合物,并且这些取代基对光物理性质的影响检查了其中的化合物。荧光性质与晶体堆积分析结果显示出良好的相关性,并且染料显示出颜色可调的固态荧光。

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