5-Phenyl-5-selanylidene-10-(2,4,6-trimethylphenyl)benzo[b][1,4]benzophosphaborinine | 913473-35-5

• 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: 5-Phenyl-5-selanylidene-10-(2,4,6-trimethylphenyl)benzo[b][1,4]benzophosphaborinine
• 英文别名: 5-phenyl-5-selanylidene-10-(2,4,6-trimethylphenyl)benzo[b][1,4]benzophosphaborinine
• CAS: 913473-35-5
• 化学式: C₂₇H₂₄BPSe
• 分子量: 469.232
• InChiKey: LGBQBODVKKBQER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  B-mesityl-P-phenylphosphaborin 在 selenium 作用下， 以 甲苯 为溶剂， 以61%的产率得到5-Phenyl-5-selanylidene-10-(2,4,6-trimethylphenyl)benzo[b][1,4]benzophosphaborinine
  参考文献：
  名称：

  Synthesis, Optical Properties, and Reactivities of A Dibenzophosphaborin and Its Derivatives

  摘要：

  Dibenzo-1,4-phosphaborins were synthesized and characterized by X-ray crystallographic analysis. The phosphaborins exhibited UV/vis absorption derived from intramolecular charge transfer from the phosphorus atom to the boron atom. The phosphaborins showed different fluorescent properties depending on the substituents on the phosphorus atom. The phosphaborin was easily derivatized to P-sulfide, P-selenide and phosphonium salt. The phosphaborin and its P-derivatives formed complexes with fluoride ion. The complex formation constants were shown to increase in accordance with the decrease in their LUMO energy levels.

  DOI：

  10.1080/10426500701735296

文献信息

• Tuning of the Optical Properties and Lewis Acidity of Dibenzopnictogenaborins by Modification on Bridging Main Group Elements
  作者：Tomohiro Agou、Junji Kobayashi、Takayuki Kawashima

  DOI：10.1021/ic061055q

  日期：2006.10.30

  Dibenzophosphaborin 1 and dibenzoazaborine 7 have been synthesized from the corresponding dibromides and MesB(OMe)(2). Dibenzophosphaborin P-sulfide 2, the P-selenide 3, and the phosphonium salt 4 were obtained by the reaction of 1 with S-8, elemental selenium, and benzyl bromide, respectively. Crystallographic analysis of 1-3 and 7 showed that the dibenzophosphaborin framework does not have a planar structure, which is caused by the pyramidalization around the phosphorus atoms, unlike in 7. Compound 1 showed a blue-shifted and weak UV-vis absorption relative to 7, indicating a weak electronic interaction between the phosphorus lone pair electrons and the pi-orbitals on the dibenzopnictogenaborin framework. The longest absorption bands of 2 and 3 are attributable to the intramolecular electron transfer from the lone pair electrons on the chalcogen atoms to the pi* orbitals on the dibenzophosphaborin framework, and the existence of these electronic transitions is supported by TD-DFT calculations. The UV-vis and B-11 NMR spectra of 4 showed a temperature-dependent change due to the coordination of a counter bromide anion to the boron center, indicating a strong Lewis acidity of the boron center. We also investigated the complex formation ability of dibenzopnictogenaborin to fluoride or chloride anions. The complex formation constants increased in accordance with the decrease in LUMO energy levels calculated using the DFT method. Compound 4 exhibited an anomalously high complex formation ability among these compounds, due to the strong electron-withdrawing effect of the phosphonium cation moiety.
• Synthesis, Optical Properties, and Reactivities of A Dibenzophosphaborin and Its Derivatives
  作者：Junji Kobayashi、Tomohiro Agou、Takayuki Kawashima

  DOI：10.1080/10426500701735296

  日期：2008.1.14

  Dibenzo-1,4-phosphaborins were synthesized and characterized by X-ray crystallographic analysis. The phosphaborins exhibited UV/vis absorption derived from intramolecular charge transfer from the phosphorus atom to the boron atom. The phosphaborins showed different fluorescent properties depending on the substituents on the phosphorus atom. The phosphaborin was easily derivatized to P-sulfide, P-selenide and phosphonium salt. The phosphaborin and its P-derivatives formed complexes with fluoride ion. The complex formation constants were shown to increase in accordance with the decrease in their LUMO energy levels.