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Asymmetric meso-CF3-BODIPY dyes based on cycloalkanopyrroles
Dyes and Pigments ( IF 4.5 ) Pub Date : 2020-01-22 , DOI: 10.1016/j.dyepig.2020.108228
Denis N. Tomilin , Elena F. Sagitova , Konstantin B. Petrushenko , Lyubov N. Sobenina , Igor A. Ushakov , Guoqiang Yang , Rui Hu , Boris A. Trofimov

New meso-CF3-substituted BODIPY derivatives have been synthesized using the methodology that includes as a key step the condensation of pyrroles with trifluoro(2,3-cycloalkanopyrrol-2-yl)ethanols. The further reaction of dipyrromethanes thus obtained with DDQ followed by complexation with BF3 leads to either benzo[b]-fused (in the case of dipyrromethanes obtained from trifluoro(4,5,6,7-tetrahydroindol-2-yl)ethanol) or cycloheptano[b]-fused saturated or partially saturated BODIPY dyes. The latter exhibit strong red fluorescence (λem = 588–634 nm, Φf = 0.54–0.68), while benzo[b]-fused do not fluoresce at all in either polar or non-polar solvents. The performed quantum-chemical calculations (TD-CAM-B3LYP/SVP) explain the spectroscopic results.



中文翻译:

基于环烷吡咯的不对称内消旋-CF 3 -BODIPY染料

已经使用包括作为关键步骤的吡咯与三氟(2,3-环烷吡咯-2-基)乙醇缩合的方法合成了新的内消旋CF 3-取代的BODIPY衍生物。如此获得的二吡咯甲烷与DDQ进一步反应,然后与BF 3络合导致苯并[b]稠合(在二吡咯甲烷由三氟(4,5,6,7-四氢吲哚-2-基)乙醇制得的情况下)或环庚烷[b]稠合的饱和或部分饱和的BODIPY染料。后者表现出强烈的红色荧光(λ EM  = 588-634纳米,Φ ˚F = 0.54–0.68),而在极性或非极性溶剂中,苯并[b]融合均不发出荧光。进行的量子化学计算(TD-CAM-B3LYP / SVP)解释了光谱结果。

更新日期:2020-01-22
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