4,4-difluoro-8-(2,3-dimethoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4-difluoro-8-(2,3-dimethoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 10-(2,3-Dimethoxyphenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2 inverted exclamation mark,1 inverted exclamation mark-f][1,3,2]diazaborinin-4-ium-5-uide；8-(2,3-dimethoxyphenyl)-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• 化学式: C₂₁H₂₃BF₂N₂O₂
• 分子量: 384.234
• InChiKey: OSLOPRHITKATDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二甲基吡咯 、 2,3-二甲氧基苯甲醛 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以38%的产率得到4,4-difluoro-8-(2,3-dimethoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Design and Synthesis of a Library of BODIPY-Based Environmental Polarity Sensors Utilizing Photoinduced Electron-Transfer-Controlled Fluorescence ON/OFF Switching

  摘要：

  We systematically examined the mechanism of the solvent polarity dependence of the fluorescence ON/OFF threshold of the BODIPY (boron dipyrromethene) fluorophore and the role of photoinduced electron transfer (PeT). In a series of BODIPY derivatives with variously substituted benzene moieties at the 8-position, the oxidation potential of the benzene moiety became more positive and the reduction potential of the BODIPY fluorophore became more negative as the solvent polarity was decreased; consequently, the free energy change of PeT from the benzene moiety becomes larger in a more nonpolar environment. Utilizing this finding, we designed and synthesized a library of probes in which the threshold of fluorescence ON/OFF switching corresponds to different levels of solvent polarity. These environment-sensitive probes were used to examine bovine serum albumin (BSA) and living cells. The polarity at the surface of albumin was concluded to be similar to that of acetone, while the polarity of the internal membranes of HeLa cells was similar to that of dichloromethane.

  DOI：

  10.1021/ja068551y

文献信息

• Heavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction
  作者：Wenbin Hu、Yanhe Lin、Xian-Fu Zhang、Mingna Feng、Siwen Zhao、Jing Zhang

  DOI：10.1016/j.dyepig.2019.01.019

  日期：2019.5

  lifetime, excited triplet state formation, and singlet oxygen formation properties are measured. DFT quantum chemical computation is also carried out to explain the experiments. The occurrence of intra-molecular CT is confirmed by UV-Vis absorption, fluorescence properties and quantum chemical computation. The triplet excited state formation is evidenced by laser flash photolysis technique. The quantitative

  在产生单线态氧（以测试的电荷转移（CT）的可调谐性的基于BODIPY光敏剂1 Δ克），十二内消旋已经合成并完全表征了-苯基-BODIPY（供体-受体）型化合物，其中苯基部分分别被0、1、2和3个甲氧基改性以增加其电子给体能力。测量了UV-Vis吸收光谱，荧光发射光谱，荧光量子产率，荧光寿命，激发三重态形成和单重态氧形成性质。还进行了DFT量子化学计算以解释实验。通过UV-Vis吸收，荧光性质和量子化学计算证实了分子内CT的发生。通过激光闪光光解技术证明了三重激发态的形成。通过DPBF（二苯基异苯并呋喃）化学捕集方法证明了光敏单线态氧的定量形成。 这种类型的CT BODIPY光敏剂的显示产生单线态氧良好的可调谐性（1 Δ克）。当供体上的甲氧基数增加时（使CT增强），单线态氧的生成效率从0.070升高到0.30。当溶剂极性增加（CT也增强）时，单线态氧的产生效率也显着提高。单线态氧产生的增加伴
• Design and Synthesis of a Library of BODIPY-Based Environmental Polarity Sensors Utilizing Photoinduced Electron-Transfer-Controlled Fluorescence ON/OFF Switching
  作者：Hisato Sunahara、Yasuteru Urano、Hirotatsu Kojima、Tetsuo Nagano

  DOI：10.1021/ja068551y

  日期：2007.5.1

  We systematically examined the mechanism of the solvent polarity dependence of the fluorescence ON/OFF threshold of the BODIPY (boron dipyrromethene) fluorophore and the role of photoinduced electron transfer (PeT). In a series of BODIPY derivatives with variously substituted benzene moieties at the 8-position, the oxidation potential of the benzene moiety became more positive and the reduction potential of the BODIPY fluorophore became more negative as the solvent polarity was decreased; consequently, the free energy change of PeT from the benzene moiety becomes larger in a more nonpolar environment. Utilizing this finding, we designed and synthesized a library of probes in which the threshold of fluorescence ON/OFF switching corresponds to different levels of solvent polarity. These environment-sensitive probes were used to examine bovine serum albumin (BSA) and living cells. The polarity at the surface of albumin was concluded to be similar to that of acetone, while the polarity of the internal membranes of HeLa cells was similar to that of dichloromethane.