五元杂环取代BODIPY染料的合成及光谱性能研究

Synthesis and spectrum properties of several brominated five heterocyclic BODIPY dyes

以吡咯和2-呋喃甲醛、2-噻吩甲醛为原料,经缩合、氧化、环化反应合成了含新型五元杂环的BOD IPY荧光染料,进一步溴化分别得到两种一溴代染料,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,并测试了这些染料的吸收光谱和发射光谱。结果表明:所有染料随着溶剂极性的增大表现出一定的溶剂化效应,吸收和发射波长变化不大(小于10 nm),而荧光量子产率则显著降低约30%;两种噻吩取代染料比两种呋喃取代染料的发射波长红移约30 nm,斯托克斯位移增大50 nm以上。溴代染料3和4的吸收波长和发射波长较非溴代染料1和2均发生约10 nm左右的红移,荧光量子产率降低约50%,表现出明显的重原子效应。

New five-membered heterocyclic BODIPY dyes were synthesized by condensation,oxidation,cyclization taking pyrrole,2-furaldehyde and 2-thenaldhyde as the starting materials and then the monobromo-derivatives were also prepared.All these dyes were characterized by MS and 1HNMR.The absorption and emission spectra of the dyes were measured.All dyes have shown the solvent effect in different polarity solvents,little change in the absorption and emission wavelengths（less than 10 nm）,while the fluorescence quantum yield decreased 30%;The emission wavelengths of two thiophene substituted dyes have red shift 30 nm,and stokes shift increase about 50 nm more than that of furan substituted dyes.The red shift of 10 nm were detected on the absorption and emission wavelength of bromide dyes 3 and 4 according to dyes 1 and 2,and fluorescence quantum yield decreased 30%.These data indicated the heavy atom effect of the spectra.