Convenient method to access new 4,4-dialkoxy- and 4,4-diaryloxy-diaza-s-indacene dyes:: Synthesis and spectroscopic evaluation
Convenient method to access new 4,4-dialkoxy- and 4,4-diaryloxy-diaza-s-indacene dyes:: Synthesis and spectroscopic evaluation
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DOI：
10.1021/jo061567m
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发表时间：
2007-01-05
影响因子：
3.6
通讯作者：
Hibert, Marcel
中科院分区：
文献类型：
--
作者：
Tahtaoui, Chouaib;Thomas, Cecile;Hibert, Marcel
本文叙述了在AlCl3存在下用不同醇处理BODIPY 1得到的原始4,4-二氧基或4,4-二氧基-二氮杂-s-吲哚烯（BODIPY）衍生物的简单合成方法。新化合物的光谱性质与母体BODIPY 1相似，吸收和发射光谱具有相似的波段形状，摩尔吸收系数高（epsilon（lambda max）接近80000 M-1 cm(-1)），并且大多数化合物具有高荧光量子产率（Phi（exp）从0.52到0.71）。在所有新合成的化合物中，染料2h比化合物1具有更高的荧光量子产率（0.71）和寿命（4.09 ns），并且具有良好的化学稳定性，适合于基于生物细胞的检测。
A straightforward method for the synthesis of original 4,4-dialkoxy- or 4,4-diaryloxy-diaza-s-indacenes (BODIPY) derivatives obtained by treatment of BODIPY 1 with various alcohols in the presence of AlCl3 is described. The novel compounds are characterized by spectroscopic properties similar to those of the parent BODIPY 1, absorption and emission spectra with similar band shapes, high molar absorption coefficients (epsilon(lambda max) approximate to 80 000 M-1 cm(-1)), and for most of them high fluorescence quantum yields (Phi(exp) from 0.52 to 0.71). Among all of the new compounds synthesized, the dye 2h exhibits higher fluorescence quantum yield (0.71) and lifetime (4.09 ns) than compound 1 and a good chemical stability toward conditions compatible with biological cell-based assays.