4,4-difluoro-8-(4-tert-butylphenyl)-4-bora-3a,4a-diaza-s-indacene | 870753-27-8

• 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-(4-tert-butylphenyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 8-(p-tert-butylphenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene；N,N'-difluoroboryl-5-(4-tert-butylphenyl)dipyrrin；10-[4-(tert-Butyl)phenyl]-5,5-difluoro-5H-dipyrrolo[1,2-c:2 inverted exclamation mark,1 inverted exclamation mark-f][1,3,2]diazaborinin-4-ium-5-uide；8-(4-tert-butylphenyl)-2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 870753-27-8
• 化学式: C₁₉H₁₉BF₂N₂
• 分子量: 324.181
• InChiKey: AMMVJPMOUOYXEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  7.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-8-(4-tert-butylphenyl)-4-bora-3a,4a-diaza-s-indacene 、 二苯基乙炔 在 bis(benzonitrile)palladium(II) chloride 、 特戊酸银 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以76%的产率得到C₄₇H₃₇BF₂N₂
  参考文献：
  名称：

  Pd-Catalyzed Direct C–H Functionalization/Annulation of BODIPYs with Alkynes to Access Unsymmetrical Benzo[b]-Fused BODIPYs: Discovery of Lysosome-Targeted Turn-On Fluorescent Probes

  摘要：

  A highly efficient palladium-catalyzed direct C-H functionalization/annulation of BODIPYs with alkynes has been developed for the first time to construct a series of unsymmetrical benzo[b]-fused BODIPYs from readily available starting materials. These unsymmetrical benzo[b]-fused BODIPYs exhibit remarkably red-shifted emissions and larger Stokes shifts than classical BODIPY dyes. Cell imaging experiments and cytotoxicity assays demonstrate that BODIPYs 4c and 4d have specific lysosome-labeling capacities, turn-on fluorescence emissions in cells, and low cytotoxicity.

  DOI：

  10.1021/acs.joc.8b01239
• 作为产物：
  描述：

  对叔丁基苯甲醛 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 4,4-difluoro-8-(4-tert-butylphenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  溴化BODIPY的合成，结构，光物理，电化学性质和抗菌活性†

  摘要：

  合成并表征了一系列单溴和二溴BODIPY（1-5），以研究染料对抗菌活性的性能。在BODIPY核心的2位和2,6-位进行区域选择性溴化反应，定量收率。内消旋-（4-羟苯基）BODIPY（5）的溴化反应出乎意料的二溴衍生物，其中溴基团安装在苯环的3,5-位而不是BODIPY核的2,6-位，由紫外线可见，荧光和1证实并支持1 H NMR光谱分析，电化学研究以及还通过单晶X射线晶体学。对于在BODIPY核心处安装的每个溴基团，我们观察到CH 2 Cl 2的吸收光谱中的红移约为16nm，发射光谱中的偏移为20-29nm 。母体和二溴衍生物的一阶还原电位之间的微小差异（5和5b）表明在溴的部分上没有发生二溴化反应。涉及C⋯H，F⋯H，H⋯H和Br⋯H的分子间相互作用是稳定分子晶体堆积的关键因素。研究了这些染料的抗菌特性，溴化衍生物显示出比其相应的母体BODIPY更好的抗菌效果，尤其是不寻常的二溴衍生物5b。

  DOI：

  10.1039/c6ra12258b

文献信息

• Structural Control of the Photodynamics of Boron−Dipyrrin Complexes
  作者：Hooi Ling Kee、Christine Kirmaier、Lianhe Yu、Patchanita Thamyongkit、W. Justin Youngblood、Matthew E. Calder、Lavoisier Ramos、Bruce C. Noll、David F. Bocian、W. Robert Scheidt、Robert R. Birge、Jonathan S. Lindsey、Dewey Holten

  DOI：10.1021/jp0525078

  日期：2005.11.1

  Boron-dipyrrin chromophores containing a 5-aryl group with or without internal steric hindrance toward aryl rotation have been synthesized and then characterized via X-ray diffraction, static and time-resolved optical spectroscopy, and theory. Compounds with a 5-phenyl or 5-(4-tert-butylphenyl) group show low fluorescence yields (similar to 0.06) and short excited-singlet-state lifetimes (similar to 500 ps), and decay primarily (> 90%) by nonradiative internal conversion to the ground state. In contrast, sterically hindered analogues having an o-tolyl or mesityl group at the 5-position exhibit high fluorescence yields (similar to 0.9) and long excited-state lifetimes (similar to 6 ns). The X-ray structures indicate that the phenyl or 4-tert-butylphenyl ring lies at an angle of similar to 60 degrees with respect to the dipyrrin framework whereas the angle is similar to 80 degrees for mesityl or o-tolyl groups. The calculated potential energy surface for the phenyl-substituted complex indicates that the excited state has a second, lower energy minimum in which the nonhindered aryl ring rotates closer to the mean plane of the dipyrrin, which itself undergoes some distortion. This relaxed, distorted excited-state conformation has low radiative probability as well as a reduced energy gap from the ground state supporting a favorable vibrational overlap factor for nonradiative deactivation. Such a distorted conformation is energetically inaccessible in a complex bearing the sterically hindered o-tolyl or mesityl group at the 5-position, leading to a high radiative probability involving conformations at or near the initial Franck-Condon form of the excited state. These combined results demonstrate the critical role of aryl-ring rotation in governing the excited-state dynamics of this class of widely used dyes.
• COMPOUND AND OPTICAL FILM COMPRISING SAME
  申请人：LG CHEM, LTD.

  公开号：US20230287008A1

  公开（公告）日：2023-09-14

  The present specification relates to a compound represented by Chemical Formula 1, a composition for forming an optical film and an optical film including the same, and a display device including the optical film.