2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-10-(2-(6-methylpyridin-2-yl)-1H-benzo[d]imidazol-6-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium | 883567-17-7

• 英文名称: 2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-10-(2-(6-methylpyridin-2-yl)-1H-benzo[d]imidazol-6-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
• CAS: 883567-17-7
• 化学式: C₃₀H₃₂BF₂N₅
• 分子量: 511.425
• InChiKey: UKAWHNOHAUIHED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  38.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.51
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3,4-二硝基苯甲酰氯 在 triethylamine 、 catalyst: Pd/C 、 p-toluenesulfonic acid 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-10-(2-(6-methylpyridin-2-yl)-1H-benzo[d]imidazol-6-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  Boron dipyrromethene dyes: a rational avenue for sensing and light emitting devices

  摘要：

  含有硝基、氨基、异氰酸酯和异硫氰酸酯基团的硼双吡咯美啶染料可以在温和条件下轻松制备。各种组合允许在附加苯基的3、4和5位取代位置生成尿素、二尿素、硫脲和二硫脲。3,4-取代的二氨基衍生物与1,10-菲啰啉-5,6-二酮和6-甲醛-2-甲基吡啶的缩合反应可以制备双吡啶苯嗪和吲哚衍生物。3,5-二硝基取代的 indacene 染料的 X 射线分子结构表征显示出二硝基苯基相对于 indacene 核心有明显的倾斜角（约 84°），而一个硝基基本与苯环共面，另一个的倾斜角约为 21°。这些染料的光学性质显示出从硝基化合物到氨基化合物再到尿素的荧光开/关切换，这可能在光诱导电子转移过程中得到理解。

  DOI：

  10.1039/b516222j

文献信息

• Isocyanate-, Isothiocyanate-, Urea-, and Thiourea-Substituted Boron Dipyrromethene Dyes as Fluorescent Probes
  作者：Raymond Ziessel、Laure Bonardi、Pascal Retailleau、Gilles Ulrich

  DOI：10.1021/jo0600151

  日期：2006.4.1

  Boron dipyrromethene dyes (Bodipy) bearing a meso-phenyl substituent carrying a variety of functional groups can be prepared under mild conditions. A single-crystal X-ray structure determination for the 3,5-dinitrophenyl compound shows the phenyl ring to be almost orthogonal (dihedral angle 84 degrees) to the plane of the Bodipy core, with one nitro group almost coplanar with the ring and the other tilted by similar to 21 degrees. Nitro substituents at the 3-, 4-, and 5- positions of the phenyl group are readily reduced to the corresponding amino groups and then converted to isocyanato, isothiocyanato, urea, thiourea, and some polyimine derivatives, the last providing additional functionality (phenazine and pyridylindole units) suitable for chelation of metal ions. All compounds are redox active, the electron-transfer processes being assigned on the basis of comparisons with model compounds. Their fluorescence properties are sensitive to the phenyl group substituents. The Bodipy unit excited state appears to be a strong reductant (E degrees similar to - 1.4 V) and a modest oxidant (E degrees similar to + 1.0 V). Quenching processes in the nitro and phenazine derivatives appear to involve intramolecular photoinduced electron transfer.