4-(5,5-difluoro-3,7-dimethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-10-yl)benzonitrile | 865479-45-4

• 英文名称: 4-(5,5-difluoro-3,7-dimethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-10-yl)benzonitrile
• 英文别名: 4,4-difluoro-3,5-dimethyl-8-(4-cyanophenyl)-4-bora-3a,4a-diaza-s-indacene
• CAS: 865479-45-4
• 化学式: C₁₈H₁₄BF₂N₃
• 分子量: 321.137
• InChiKey: TZYJUVPOOPOTCC-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  4-(5,5-difluoro-3,7-dimethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-10-yl)benzonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 二异丙醇胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  β-β-炔基桥接 BODIPY 二聚体：合成、单光子和双光子光物理性质

  摘要：

  通过改变中间位置的EDG和EWG的性质，合成了具有不同EDG-EDG和EDG-EWG的六种β-β-连接的BODIPY二聚体。两个内消旋位置具有相同取代基的z4和z5的荧光寿命和量子产率远高于具有两个不同取代基的BODIPY二聚体。化合物z4表现出最高的荧光量子产率（11.24%）和荧光寿命（1.32ns）。化合物 z4 和 z5 在 800–1000 nm 区域显示出重要的双光子诱导荧光，发射强度与激光激发功率之间存在明显的二次依赖性。

  DOI：

  10.1016/j.molstruc.2024.138313
• 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-(5,5-difluoro-3,7-dimethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-10-yl)benzonitrile
  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

• 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)).