5,5-difluoro-8-formyl-1,3,7,9,10-pentamethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide | 198149-19-8

• 英文名称: 5,5-difluoro-8-formyl-1,3,7,9,10-pentamethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
• 英文别名: 5,5-difluoro-1,3,7,9,10-pentamethyl-5H-5λ⁴,6λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2-carbaldehyde
• CAS: 198149-19-8
• 化学式: C₁₅H₁₇BF₂N₂O
• 分子量: 290.121
• InChiKey: PUOVUIQTGSBWQA-UHFFFAOYSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  5,5-difluoro-8-formyl-1,3,7,9,10-pentamethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以56%的产率得到
  参考文献：
  名称：

  Photo-physical aspects of BODIPY-coumarin conjugated sensor and detection of Al³⁺in MCF-7 cell

  摘要：

  BODIPY azine bearing chemosensor R1 has been synthesised for selective detection of Al(3+)with visual colour change from red-purple to purple and photo-physical studies were explained through Forster Resonance Energy Transfer (FRET) mechanism. Chemosensor showed good sensing capability with high binding constant and lower Limit of Detection (LOD) towards Al3+. Cell viability and fluorescence microscopic experiments illustrated about the cytocompatibily of the sensor in presence of Al3+ in living cells (MCF-7).

  DOI：

  10.1080/10610278.2019.1659267
• 作为产物：
  描述：

  在 水 作用下， 以 水 、 乙腈 为溶剂， 生成 5,5-difluoro-8-formyl-1,3,7,9,10-pentamethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
  参考文献：
  名称：

  Recognition of Al3+ through the off-on mechanism as a proficient driving force for the hydrolysis of BODIPY conjugated Schiff base and its application in bio-imaging

  摘要：

  Two new BODIPY azine bearing quinoline and pyrazine attached Schiff base chemosensors (R1 and R2) have been synthesized and applied for the detection of Al3+ in CH3CN/H2O medium. Intramolecular hydrogen bonding makes both the sensors rigid and helps to encapsulate Al3+ in the cavity. The pink colour of R1 and R2 has been changed to green fluorescent upon excess addition of Al3+ which is only because of the hydrolysis of imine bond to regenerate compound 8. Another nitrogen atom present in quinoline and in pyrazine moiety made R1 and R2 more efficient in sensing of Al3+ ion compare to R1D, R2B and R2D. Cell viability and fluorescence microscopic experiments showed that the chemosensors are cytocompatible and can be used as an effective fluorescent probe for detecting Al3+ ion in the living cell.

  DOI：

  10.1016/j.ica.2019.119157

文献信息

• A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes
  作者：Hikaru Yanai、Shoki Hoshikawa、Yukiko Moriiwa、Atsushi Shoji、Akio Yanagida、Takashi Matsumoto

  DOI：10.1002/anie.202012764

  日期：2021.3

  two (trifluoromethyl)sulfonyl (Tf=SO2CF3) groups, into several fluorescence dyes including boron‐dipyrromethenes (BODIPYs), fluoresceins, and aminocoumarins has been achieved by the 2,2‐bis(triflyl)ethylation reaction of the dye frameworks with highly electrophilic Tf2C=CH2, followed by neutralization with NaHCO3. Despite the contradiction between water solubility and lipophilicity, the carbanion‐decorated

  2,2已成功实现了将由两个（三氟甲基）磺酰基（Tf = SO 2 CF 3）基团牢固稳定的碳负离子取代基安装到几种荧光染料中，包括硼二吡咯烷酮（BODIPYs），荧光素和氨基香豆素。带有高亲电性的Tf 2 C = CH 2的染料骨架发生双（三氟乙）乙基化反应，然后用NaHCO 3中和。尽管水溶性和亲脂性之间存在矛盾，但如此获得的碳负离子修饰的染料不仅水溶性显着提高，而且亲脂性也显着提高。这项工作清楚地表明，氟化的高度稳定的碳负离子取代基是控制化学材料宏观性能的新选择。
• New 2, 6-Modified Bodipy Sensitizers for Dye-Sensitized Solar Cells
  作者：Jian-Bo Wang、Xia-Qin Fang、Xu Pan、Song-Yuan Dai、Qin-Hua Song

  DOI：10.1002/asia.201100779

  日期：2012.4

  Three novel 2,6‐modified Bodipy sensitizers were synthesized and evaluated for their use in dye‐sensitized solar cells (DSSCs). Among them, dye B3, which carries a n‐pentyl group at position 8, exhibits the best solar energy conversion efficiency (1.83 %). The results of this study provide a new strategy for the design of Bodipy derivatives as sensitizers for DSSCs.

  合成了三种新颖的2,6修饰的Bodipy敏化剂，并对其在染料敏化太阳能电池（DSSC）中的使用进行了评估。其中，在位置8上带有正戊基的染料B3表现出最佳的太阳能转化效率（1.83％）。这项研究的结果为Bodipy衍生物作为DSSC的敏化剂的设计提供了新的策略。
• Modulation of ICT probability in bi(polyarene)-based O-BODIPYs: towards the development of low-cost bright arene-BODIPY dyads
  作者：Leire Gartzia-Rivero、Esther M. Sánchez-Carnerero、Josue Jiménez、Jorge Bañuelos、Florencio Moreno、Beatriz L. Maroto、Iñigo López-Arbeloa、Santiago de la Moya

  DOI：10.1039/c7dt01984j

  日期：——

  report the synthesis, and spectroscopic and electrochemical properties of a selected library of novel spiranic O-BODIPYs bearing a phenol-based bi(polyarene) unit tethered to the boron center through oxygen atoms. These dyes constitute an interesting family of arene-BODIPY dyads useful for the development of photonic applications due to their synthetic accessibility and tunable photonic properties. It is

  我们报告的合成，光谱和电化学性质的新型螺环O-BODIPYs的选定库，该库具有通过氧原子束缚到硼中心的酚基双（聚芳烃）单元。这些染料由于其合成的可及性和可调节的光子特性，构成了一个有趣的芳烃-BODIPY二元家族，可用于开发光子应用。已证明所涉及的芳烃部分的电子供体能力在非发射性分子内电荷转移（ICT）状态上转换，这限制了二聚体的荧光效率。有趣的是，该非辐射失活通道的影响可以通过在二吡啶配体或在聚芳烃部分上的取代模式来有效地调节。因此，具有富电子的双吡啶和贫电子的聚芳烃的二元组显示出更低或几乎可以忽略的ICT机率，因此在远处的光谱区域受到双重激发时显示出明亮的荧光。该合成方法已允许低成本的易开发高效紫外线吸收可见光发射通过选择适当的参与键单元，dipyrrin和双（polyarene）的取代模式盒，以调节不仅吸收和发射波长，也荧光效率。
• Controlling Vilsmeier-Haack processes in meso-methylBODIPYs: A new way to modulate finely photophysical properties in boron dipyrromethenes
  作者：Eduardo Palao-Utiel、Laura Montalvillo-Jiménez、Ixone Esnal、Ruth Prieto-Montero、Antonia R. Agarrabeitia、Inmaculada García-Moreno、Jorge Bañuelos、Iñigo López-Arbeloa、Santiago de la Moya、Maria J. Ortiz

  DOI：10.1016/j.dyepig.2017.02.030

  日期：2017.6

  meso-methylBODIPYs to Vilsmeier-Haack reaction conditions. These competitive processes generate BODIPYs with opposed photophysical properties, from highly fluorescent dyes enabling laser emission, to non-fluorescent singlet-oxygen photosensitizers. The synthetic control is exerted on the basis of the structure of the starting BODIPY, as well as the electrophilic character (hard or soft) of the formylating reagent

  在本文的工作中，我们报告了将内消旋-甲基BODIPY提交至Vilsmeier-Haack反应条件时对竞争过程的精细控制。这些竞争过程产生具有相反光物理性质的BODIPY，从能够发出激光的高荧光染料到无荧光单线态氧光敏剂。综合控制是基于起始BODIPY的结构以及甲酰化试剂的亲电子特性（硬或软）来进行的。
• Managing nucleophilic addition reactions to tune the physical properties of 2-substituted pentamethylBODIPY derivatives
  作者：S. R. Sritharan、B. A. Hussein、D. D. Machin、M. A. El-Aooiti、J. A. Adjei、J. K. Singh、J. T. H. Pau、J. S. Dhindsa、A. J. Lough、B. D. Koivisto

  DOI：10.1039/c6ra28114a

  日期：——

  The synthesis and characterization of a family of 2-substituted BODIPY dyes are reported herein. The dyes have been prepared using nucleophilic addition reactions (Wittig reactions, imine, Knoevenagel & aldol condensations) which are typically more challenging for BODIPY ring systems. Structure–property relationships have also been delineated by evaluating the physicochemical properties including;

  本文报道了2-取代的BODIPY染料家族的合成和表征。染料是使用亲核加成反应（维蒂希反应，亚胺，Knoevenagel和羟醛缩合反应）制备的，通常对BODIPY环系统而言更具挑战性。通过评估其理化性质还可以确定结构与性质之间的关系，包括：吸收和发射光谱，电化学研究（CV，DPV）和理论计算（TD-DFT）。