Synthesis and Structural Diversification of Circularly Polarised Luminescence Active, Helically Chiral, "Confused" N , N , O , C -BODIPYs**
Synthesis and Structural Diversification of Circularly Polarised Luminescence Active, Helically Chiral, "Confused" N , N , O , C -BODIPYs**
复制标题
圆偏振发光活性、螺旋手性、“混淆”N、N、O、C -BODIPYs** 的合成和结构多样化**
DOI：
10.1002/cptc.202200194
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发表时间：
2022
期刊：
影响因子：
3.7
通讯作者：
Clarke R
中科院分区：
文献类型：
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作者：
Clarke R
已知螺旋手性硼螯合的二吡咯亚甲基（BODIPY）染料表现出溶液相圆偏振发光（CPL），但实例限于几种合成可获得的分子结构。我们报告了一个B−N螯合，SNAr，Suzuki交叉偶联，B−O螯合级联反应，用于从容易获得的3，5-二溴-BODIPY起始材料合成研究不足的螺旋手性，N，N，O，C-硼螯合，“混淆”BODIPY。使用这种方法，我们制备了一系列具有3，5-取代基变化的螺旋手性“混淆”BODIPY。通过手性HPLC拆分后，通过比较实验和计算的ECD光谱来指定绝对立体化学，并确定溶液相手性性质，包括CPL（|闷闷不乐|从2.1到3.7×10−3; BCPL从11.3到27.2）。
Helically chiral boron‐chelated dipyrromethene (BODIPY) dyes are known to exhibit solution phase circularly polarized luminescence (CPL), but examples are limited to a few synthetically accessible molecular architectures. We report a B−N chelation, SNAr, Suzuki cross‐coupling, B−O chelation cascade reaction for the synthesis of understudied helically chiral,N,N,O,C‐boron chelated, “confused” BODIPYs, from readily accessible 3,5‐dibromo‐BODIPY starting materials. Using this approach we have prepared a series of helically chiral “confused” BODIPYs with variation of the 3,5‐subsitutents. Following resolution by chiral HPLC, absolute stereochemistry was assigned through comparison of the experimental and calculated ECD spectra, and solution phase chiroptical properties including CPL were determined (|glum| from 2.1 to 3.7×10−3;BCPLfrom 11.3 to 27.2).