4,4-difluoro-3,5-dimethyl-8-(4-morpholinophenyl)-4-bora-3a,4a-diaza-s-indacene | 865479-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4,4-difluoro-3,5-dimethyl-8-(4-morpholinophenyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 5,5-difluoro-3,7-dimethyl-10-(4-morpholinophenyl)-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
• CAS: 865479-48-7
• 化学式: C₂₁H₂₂BF₂N₃O
• 分子量: 381.233
• InChiKey: YDTPKZLNXQMDGP-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：

  2-甲基吡咯 、 4-(4-吗啉)苯甲醛 、 三氟化硼乙醚 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以11%的产率得到4,4-difluoro-3,5-dimethyl-8-(4-morpholinophenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  用给电子氨基修饰内消旋苯基可大大增强BODIPY作为单线态氧光敏剂的能力

  摘要：

  我们合成了三种1,3,5,7-四甲基-BODIPY（1a，2a，3a）和三种3,5-二甲基-BODIPY（1b，2b，3b）光敏剂，其中内消旋位置被不同的对位修饰-氨基苯基。通过紫外可见吸收光谱，荧光发射光谱方法研究了BODIPYs的单线态氧的产生和光物理性质。发现这些BODIPY衍生物是环境敏感的和荧光光敏剂，其在中等极性环境中显示出产生单线态氧的高效率，而在极性和非极性溶剂中几乎没有光活性。同时，它们在非极性溶剂中具有高荧光性，但在极性溶剂中的发射性低得多，ICT发射发生在中等极性溶剂中，并且与单线态氧的形成效率相关。该结果通过PCT（光致电荷转移）机理来解释。在1和7位上甲基的存在会导致苯环无法旋转，因此，与BODIPY 1b， 2b和3b相比， 1a， 2a和3a的单线态氧产生效率和荧光量子产率明显高。

  DOI：

  10.1016/j.dyepig.2017.10.018

文献信息

• Photophysical Properties of Borondipyrromethene Analogues in Solution
  作者：Wenwu Qin、Mukulesh Baruah、Mark Van der Auweraer、Frans C. De Schryver、Noël Boens

  DOI：10.1021/jp052626n

  日期：2005.8.1

  The photophysical properties of seven new 8-(p-substituted)phenyl analogues of 4,4-difluoro-3,5-dimethyl-8-(aryl)-4-bora-3a,4a-diaza-s-indacene (derivatives of the well-known fluorophore BODIPY) in several solvents have been studied by means of absorption and steady-state and time-resolved fluorimetry. For each compound, the fluorescence quantum yield and lifetime are lower in solvents with higher polarity owing to an increase in the rate of nonradiative deactivation. Increasing the electron withdrawing strength of the p-substituent on the phenyl group in position 8 also leads to lower fluorescence quantum yields and lifetimes. When the p-substituent on the phenyl group in position 8 is a tertiary amine [8-(4-piperidinophenyl), 8-(4-N,N-dimethylaminophenyl), and 8-(4-morpholinophenyl)], the low quantum yields of these compounds in more polar solvents can be rationalized by the inversion of the energy levels of an apolar, highly fluorescent and a polar, nonfluorescent excited state, where charge transfer from the tertiary amine to the BODIPY unit occurs. These amine analogues can be protonated at low pH in aqueous solution. Fluorescence titrations yielded pK(a) values of their conjugate ammonium salts which are in agreement with the electron donating tendency of the amine group: piperidino (4.15) > dimethylamino (2.37) > morpholino (1.47), with the pK(a) values in parentheses. The rate constant of radiative deactivation (k(f)) is the same for all compounds in all solvents studied (k(f) = 1.4 x 10(8) s(-1)).