5-(4-三氟甲基苯基)二吡咯甲烷 | 247128-02-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 5-(4-三氟甲基苯基)二吡咯甲烷
• 英文名称: 5-(4-trifluoromethylphenyl)dipyrromethane
• 英文别名: 2,2 inverted exclamation mark-[[4-(Trifluoromethyl)phenyl]methylene]bis(1H-pyrrole)；2-[1H-pyrrol-2-yl-[4-(trifluoromethyl)phenyl]methyl]-1H-pyrrole
• CAS: 247128-02-5
• 化学式: C₁₆H₁₃F₃N₂
• 分子量: 290.288
• InChiKey: VRTMFEBJAZBYQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-三氟甲基苯基)二吡咯甲烷 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Microwave-assisted reduction of F-BODIPYs and dipyrrins to generate dipyrromethanes

  摘要：

  BODIPYs和dipyrrins被还原为dipyrromethanes，通过涉及乙二醇和甲氧基钠的反应。当苄醇代替乙二醇时，在微波辐射后向反应混合物中加入2,4-二硝基苯肼会导致产生1-苄基亚甲基-2-(2,4-二硝基苯基)肼，表明与dipyrromethane同时产生醛。

  DOI：

  10.1139/cjc-2013-0341
• 作为产物：
  描述：

  4,4-difluoro-8-(4-trifluoromethylphenyl)-4-bora-3a,4a-diaza-s-indacene 在 sodium methylate 作用下， 反应 0.17h， 以53%的产率得到5-(4-三氟甲基苯基)二吡咯甲烷
  参考文献：
  名称：

  Microwave-assisted reduction of F-BODIPYs and dipyrrins to generate dipyrromethanes

  摘要：

  BODIPYs和dipyrrins被还原为dipyrromethanes，通过涉及乙二醇和甲氧基钠的反应。当苄醇代替乙二醇时，在微波辐射后向反应混合物中加入2,4-二硝基苯肼会导致产生1-苄基亚甲基-2-(2,4-二硝基苯基)肼，表明与dipyrromethane同时产生醛。

  DOI：

  10.1139/cjc-2013-0341

文献信息

• Molecular tectonics: control of pore size and polarity in 3-D hexagonal coordination networks based on porphyrins and a zinc cation
  作者：Elisabeth Kühn、Véronique Bulach、Mir Wais Hosseini

  DOI：10.1039/b812831f

  日期：——

  In the crystalline phase, porphyrin derivatives based on two 4-pyridyl units at the 5 and 15 meso positions and two 4-aryl moieties bearing various groups (CN, OMe, OH and CF3) at the 10 and 20 meso positions lead, in the presence of a zinc dication, to the formation of robust 3-D networks presenting hexagonal channels: both the size and the polarity of the pores were tuned by the nature of the substituents attached to the two aryl groups.

  在晶体相中，基于位于5和15位meso位置的两个4-吡啶单元和携带各式基团（CN、OMe、OH和CF3）位于10和20位meso位置的两个4-芳基部分的卟啉衍生物，在锌二阳离子的存在下，形成呈现六边形通道的坚固三维网络：孔隙的大小和极性均通过附着于两个芳基团上的取代基性质进行调节。
• BODIPY based A-D-A molecules: Effect of CF3 group substitution at meso phenyl group
  作者：Gourav Tarafdar、Justin C. Johnson、Bryon W. Larson、Praveen C. Ramamurthy

  DOI：10.1016/j.dyepig.2020.108289

  日期：2020.6

  fluorene and benzodithiophene as the central donor subunits and terminal BODIPY units, functionalized with either a 4-methylphenyl or 4-trifluoromethylphenyl group at the meso position. The effect of the para substituent of the meso phenyl group on the photophysical properties of these molecules is studied through steady state absorption and fluorescence spectroscopy as well as femtosecond transient

  已经合成了两对ADA分子，它们以芴和苯并二噻吩为中心供体亚基和末端BODIPY单元，并在内消旋位置被4-甲基苯基或4-三氟甲基苯基官能化。通过稳态吸收和荧光光谱以及飞秒瞬态吸收和时间分辨荧光光谱技术研究了内消旋苯基的对位取代基对这些分子的光物理性质的影响。通过在PC 60混合物中进行时间分辨的微波电导率测量，研究了这些分子作为供体在溶液处理的太阳能电池活性层中的适用性BM受体，随着取代基的选择，其电荷转移的收率变化。然后采用瞬态吸收光谱法研究了4-三氟甲基苯基在改变电荷从这些ADA分子转移至PC 60 BM的效率中的作用。结果显示了皮秒电荷转移的一致性图片，并且数百ps的新生化合物发生了重组，导致针对甲基苯基衍生物进行优化的长寿命游离电荷的收率很小。
• Synthesis and Band Gap Analysis of Designed Porphyrin Derivatives Containing Electron Donating and Accepting Group
  作者：In‐Jung Chang、Yea‐Sel Jeon、Kwang‐Jin Hwang

  DOI：10.1002/bkcs.11680

  日期：2019.2

  bispyrrole 2D, 2A1–2A5 with the corresponding aldehyde 3 or diol 6 as a key step. The UV–Vis spectrum and CV of those porphyrins were measured and analyzed for band gap and HOMO–LUMO energy. With the electron withdrawing group, the band gap of porphyrins PP was increased and that of metalloporphyrin PP–M decreased. The HOMO level of PP and LUMO level of PP–M were more lowered than the LUMO of PP and the

  通过双吡咯2D，2A1-2A5与相应的醛3或二醇6的麦克唐纳偶联，合成了对称的（DD，AA1-AA5）和非对称的（DA1）卟啉衍生物。测量并分析了这些卟啉的UV-Vis光谱和CV的带隙和HOMO-LUMO能量。随着吸电子基团的增加，卟啉PP的带隙增加，而金属卟啉PP-M的带隙减少。PP的HOMO水平和PP-M的LUMO水平比PP的LUMO和PP-M的HOMO低得多， 分别。所有PP和PP–M的LUMO能级均低于P3HT（−2.80 eV），PP和PP–M的所有HOMO能级均高于PCBM（−6.20 eV）。
• From nonconjugation to conjugation: novel meso-OH substituted dipyrromethanes as fluorescence turn-on Zn2+ probes
  作者：Yubin Ding、Tong Li、Xin Li、Weihong Zhu、Yongshu Xie

  DOI：10.1039/c3ob40121a

  日期：——

  Most reported Zn2+ probes suffer from the interference of background fluorescence originated from the conjugated structures of commonly utilized fluorophores. In this work, three novel meso-hydroxyl group substituted dipyrromethanes DPMOH1–DPMOH3 were synthesized and found to be colourless and nonfluorescent due to the interruption of the conjugated π system by an sp3 carbon between the two pyrrolic units. Interestingly, only the addition of Zn2+ to the solutions of DPMOH1–DPMOH3 promoted their oxidation to dipyrrin forms, and bright fluorescence “turn on” was observed due to the formation of corresponding dipyrrin complexes with the dipyrrin : zinc stoichiometry of 2 : 1. Zn2+ detection mechanism was investigated by UV-Vis, fluorescence, 1H NMR and HRMS analyses, which can be ascribed to the CHEF type fluorescence enhancement, resulting from good rigidity of the dipyrrin complexes. Hence, DPMOH1–DPMOH3 can be used as fluorescence turn-on Zn2+ probes with the advantage of no background fluorescence.

  大多数已报道的 Zn2+ 探针都受到来自常用荧光团共轭结构的背景荧光的干扰。在这项工作中，合成了三种新型介羟基取代的二吡咯甲烷 DPMOH1-DPMOH3，并发现由于两个吡咯单元之间的 sp3 碳打断了共轭 π 系统，因此它们是无色无荧光的。有趣的是，只有在 DPMOH1-DPMOH3 溶液中加入 Zn2+ 才能促进它们氧化成二吡咯啉形式，并观察到明亮的荧光 "开启"，这是因为形成了相应的二吡咯啉配合物，二吡咯啉与锌的化学计量为 2 ：1.通过紫外-可见光、荧光、1H NMR 和 HRMS 分析研究了 Zn2+ 的检测机理，这可归因于二吡咯啉络合物良好的刚性导致的 CHEF 型荧光增强。因此，DPMOH1-DPMOH3 具有无背景荧光的优点，可用作荧光开启型 Zn2+ 探针。
• A novel method for the synthesis of dipyrromethanes by metal triflate catalysis
  作者：Baris Temelli、Canan Unaleroglu

  DOI：10.1016/j.tet.2006.08.047

  日期：2006.10

  5-Substituted dipyrromethanes were synthesized by the reaction of N-tosyl imines with excess pyrrole in the presence of metal triflates. Tripyrromethane and other oligomeric side products were not observed. High yields of 5-substituted dipyrromethanes were obtained for electron donating and withdrawing substituents by performing the reaction at two different temperatures. The new reaction procedure

  在三氟甲磺酸金属盐存在下，N-甲苯磺酰基亚胺与过量的吡咯反应合成了5位取代的二吡咯甲烷。未观察到三吡咯甲烷和其他低聚副产物。通过在两个不同的温度下进行反应，可获得高产率的5-取代的二吡咯甲烷，用于给电子和撤离取代基。新的反应程序简单，不需要无水条件。