4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene | 865479-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-difluoro-8-(4-methoxyphenyl)-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene
• CAS: 865479-40-9
• 化学式: C₁₈H₁₇BF₂N₂O
• 分子量: 326.154
• InChiKey: IOOSLTBTHQJDKB-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：
  None
• 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-吡咯甲醛 在 hydrazine hydrate 、 四甲基乙二胺 、 3,4-bis((3,5-bis(trifluoromethyl)phenyl)amino)cyclobut-3-ene-1,2-dione 、 氢气 、 palladium diacetate 、 sodium hydroxide 、 正丁基二(1-金刚烷基)膦 作用下， 以 甲苯 为溶剂， 20.0~160.0 ℃ 、1.0 MPa 条件下， 反应 76.5h， 生成 4,4-difluoro-3,5-dimethyl-8-(4-methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  羰基化作为新串联反应的关键步骤——通往 BODIPY 的途径

  摘要：

  在此，提出了 BODIPY 的高效五步反应序列。 55 种衍生物的合成总产率高达 78%，这表明我们能够扩大易于获得的 BODIPY 的范围，同时证明我们开发的方法的普遍适用性和优势。

  DOI：

  10.1002/chem.202303752

文献信息

• Enabling Regioselective Synthesis of α‐Methyl BODIPYs via H2O2/DMSO‐Promoted Direct Methylation
  作者：Fan Lv、Shuangshuang Zhu、Zhong‐Yuan Li、Wangfei Wang、Hua Wang、Lijuan Jiao、Erhong Hao

  DOI：10.1002/adsc.202400346

  日期：2024.7.16

  Achieving α‐methylation of BODIPYs remains challenging due to the electron‐deficient property of α‐position of BODIPYs. Herein, a H2O2/DMSO‐promoted radical process was employed, providing an approach for the construction of a series of α‐methyl and α,α‐dimethyl BODIPYs in 57‐68% yields. In addition, representative transformations and half‐gram experiments as well as their photophysical properties

  由于 BODIPY α 位的缺电子特性，实现 BODIPY 的 α-甲基化仍然具有挑战性。在此，采用H2O2/DMSO促进的自由基过程，提供了构建一系列α-甲基和α，的方法α-二甲基 BODIPY 产率为 57-68%。此外，还研究了代表性变换和半克实验及其光物理性质，以检验潜在的应用。
• Synthesis, electrochemical/photophysical properties and computational investigation of 3,5-dialkyl BODIPY fluorophores
  作者：Yavuz Derin、Raşit Fikret Yılmaz、İbrahim Halil Baydilek、Vildan Enisoğlu Atalay、Abdil Özdemir、Ahmet Tutar

  DOI：10.1016/j.ica.2018.06.006

  日期：2018.10

  A series of 3,5 dimethyl and diethyl BODIPY with different substitutions at meso position are synthesized and characterized. Photophysical and electrochemical features of the 3,5 dialkyl BODIPY fluorophores are investigated using experimental and computational approaches. All fluorophores display absorption maxima around at 510 nm and emission maxima around at 520 nm which correspound to very narrow Stokes shift. Among the fluorophores, 3,5,8 alkylated BODIPYs are found to have high fluorescence quantum yield (1.00-0.93). 4-Bromophenyl group at meso position decreases fluorescence quantum yield of the dye while it increases with 4-methoxyphenyl group at meso position. The HOMO-LUMO energies of synthesized fluorophore compounds were calculated by B3LYP/6-31G(d, p) and B3LYP/6-311+ G(d, p) levels in chloroform phase. Electron donating and accepting groups show increasing and decreasing effect on the band gaps of the fluorophores respectively.
• 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)).