3-thien-3-yl-8-(2,6-dichlorophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 1395897-61-6

• 英文名称: 3-thien-3-yl-8-(2,6-dichlorophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• CAS: 1395897-61-6
• 化学式: C₁₉H₁₁BCl₂F₂N₂S
• 分子量: 419.09
• InChiKey: NMLDUIWNKCYOOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  3-溴噻吩 、 10-(2,6-dichlorophenyl)-5,5-difluoro-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine 在 tricyclohexylphosphine tetrafluoroborate 、 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以26%的产率得到3-thien-3-yl-8-(2,6-dichlorophenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Direct palladium-catalysed C–H arylation of BODIPY dyes at the 3- and 3,5-positions

  摘要：

  开发了一种通过钯催化的 C–H 芳基化一步合成 3- 和 3,5-芳基化 BODIPY 染料的新方法，并对其适用范围进行了研究。

  DOI：

  10.1039/c2cc34549h

文献信息

• UV—vis spectroscopy of the coupling products of the palladium-catalyzed C—H arylation of the BODIPY core
  作者：Lina Wang、Bram Verbelen、Claire Tonnelé、David Beljonne、Roberto Lazzaroni、Volker Leen、Wim Dehaen、Noël Boens

  DOI：10.1039/c3pp25385f

  日期：2013.5

  The steady-state, UV—vis electronic absorption and fluorescence emission properties of a large set of 3-aryl and 3,5-diaryl substituted difluoroboron dipyrromethene dyes obtained via direct, palladiumcatalyzed C—H (het)arylation of the BODIPY core are reported. The spectra display the narrow absorption and fluorescence emission bands and the generally quite small Stokes shifts characteristic of classic difluoroboron dipyrrins. As a function of the solvent, the spectral maxima are located within a very narrow wavelength range and are slightly red-shifted with increasing solvent polarizability, which is shown to be the crucial parameter influencing the wavelength position of the maxima. The extended π-conjugation in the 3,5-diaryl products always leads to bathochromically shifted absorption and emission spectra compared to those of the 3-aryl analogues. The derivative with a 3-mesityl substituent has blue-shifted spectra in comparison to its 3-phenyl substituted analogue, reflecting the diminished π-conjugation in the former due to steric strain. The nature of the meso-aryl has only a small effect on the spectral positions but affects the fluorescence quantum yield Φ. The majority of the dyes have high Φ (>0.85), except the compounds with meso-phenyl and meso-(p-nitrophenyl) substituents. Quantumchemical calculations were performed to evaluate the differences in spectroscopic properties upon substitution of the BODIPY core and to compare them with the corresponding experimental results.

  报告了通过直接钯催化 BODIPY 核的 CH（杂）芳基化获得的大量 3-芳基和 3,5-二芳基取代的二氟硼二吡咯亚甲基染料的稳态、紫外可见电子吸收和荧光发射特性。光谱显示出经典二氟硼二吡林的窄吸收带和荧光发射带以及通常相当小的斯托克斯位移特征。作为溶剂的函数，光谱最大值位于非常窄的波长范围内，并且随着溶剂极化率的增加而轻微红移，这被证明是影响最大值波长位置的关键参数。与 3-芳基类似物相比，3,5-二芳基产物中扩展的 π-共轭总是导致吸收和发射光谱红移。与 3-苯基取代的类似物相比，具有 3-异丙基取代基的衍生物具有蓝移光谱，反映了前者由于空间应变而减少了 π 共轭。内消旋芳基的性质对光谱位置只有很小的影响，但会影响荧光量子产率Φ。除具有内消旋苯基和内消旋（对硝基苯基）取代基的化合物外，大多数染料具有高Φ（>0.85）。通过量子化学计算来评估取代 BODIPY 核后光谱特性的差异，并将其与相应的实验结果进行比较。