溴代呋喃杂环取代BODIPY染料的合成及光谱性能研究

Synthesis and Spectral Properties of Several Novel Brominated Five-ring Heterocyclic BODIPY Dyes

通过吡咯和2-呋喃甲醛经一步法合成了新型含呋喃环的BODIPY荧光染料,并进一步溴化合成了一溴和二溴五元杂环类BODIPY染科,所有合成的染料分子均通过质谱、核磁等手段进行了结构表征。并测试了这些荧光染料的吸收光谱和发射光谱,研究了不同极性的溶剂对染料光谱性能的溶剂化效应以及Br原子对染料光谱的重原子效应。结果表明:随着溶剂极性的增大,所合成的染料吸收波长均发生了10 nm左右的蓝移,而染料的发射波长则红移约5 nm,荧光量子产率降低了约30%;随着染料结构中溴原子的不断增多,发射波长最终红移约30 nm左右,荧光量子产率降低75%,表现出明显的重原子效应。

Applying pyrrole and 2-furaldehyde as the starting materials new five-ring heterocyclic BODIPY fluorescent dyes and the monobromo-and dibromo-derivatives were prepared.The structures of all these dyes were characterized by MS and 1H NMR.Testing the spectral effect in different polar solvents,the heavy atom effect on bromo-dyes was investigated.With the enhancement of solvent polarity a blue shift of 10 nm was detected on the absorption wavelength of these dyes,while a red shift of 5 nm was observed on the emission wavelenth and the fluorescence quantum yield decreased 30%.Increasing the number of bromine atoms,a red shift of 30 nm was detected on emission wavelength of the dyes,and the fluorescence quantum yield decreased 75 %.These data indicated the presence of heavy atom effect on the spectra.