6,6'-bis(4-(diphenylamino)phenyl)-1,1'-binaphthyl-2,2'-diol | 1312293-40-5

• 分子结构分类: 有机化合物
• 英文名称: 6,6'-bis(4-(diphenylamino)phenyl)-1,1'-binaphthyl-2,2'-diol
• CAS: 1312293-40-5
• 化学式: C₅₆H₄₀N₂O₂
• 分子量: 772.946
• InChiKey: LPVFOJJQTIOWLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.34
• 重原子数：
  60.0
• 可旋转键数：
  9.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.94
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6,6'-bis(4-(diphenylamino)phenyl)-1,1'-binaphthyl-2,2'-diol 、 四丁基氟化铵 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  The nature of 6,6′-bis(triphenylamine) substituted BINOL as chromophoric and fluorogenic hybrid chemosensor for selective fluoride detection

  摘要：

  6,6'-Bis(triphenylamine)-1,1'-binaphthy1-2,2'-diol (1) is highly fluorescent in visible region. On treatment with a variety of anions, the UV-vis absorption as well as the fluorescent behavior of 1 in CH2Cl2 is substantially changed. Among the tetrabutylammonium (TBA) salts we tested, including F- OH- (from TBAOH in MeOH), Cl-, Br-, I-, OAc-, HSO4-, TsO- (Et4N salt), and H2PO4-, F- was found to be the most effective fluorescence quencher. Quantitative fluorescence analysis of the titration data revealed that the anions are classified into two categories: (1) Simple mono-anions, such as F- (log beta(F)(2) = 11.00 +/- 0.08), OH- (log beta(OH)(2) = 9.05 +/- 0.01), and Cl- (log beta(2) = 9.96 +/- 0.70) that follow the stoichiometry of 1:2, indicating the formation of (1.X-2)(2-) complexes; (2) Oxo-anions, such as OAc- (log beta(OAc)(1) = 5.13 +/- 0.012), H2PO4- (log beta(HP)(1) = 4.87 +/- 0.03), and TsO- (using tetraethylammonium salt, (log beta(OTs)(1) = 3.36 +/- 0.02) that show the stoichiometry of 1:1, indicating the formation of (1.X)(-) complexes. The complexation behaviors were further confirmed by H-1 NMR spectroscopy. In the co-crystal prepared from 1,1-binaphthy1-2,2'-diol (BINOL) and Et4NF, F- and BINOL are assembled to form a linear polymeric array, with a dimeric group of BINOL/BINOL anions linked as the side-chains. Intramolecular hydrogen bond was observed within the BINOL anion. This provides structural insights about the BINOL-fluoride complex formation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.047
• 作为产物：
  描述：

  (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol 、 4-硼酸三苯胺 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以32%的产率得到6,6'-bis(4-(diphenylamino)phenyl)-1,1'-binaphthyl-2,2'-diol
  参考文献：
  名称：

  The nature of 6,6′-bis(triphenylamine) substituted BINOL as chromophoric and fluorogenic hybrid chemosensor for selective fluoride detection

  摘要：

  6,6'-Bis(triphenylamine)-1,1'-binaphthy1-2,2'-diol (1) is highly fluorescent in visible region. On treatment with a variety of anions, the UV-vis absorption as well as the fluorescent behavior of 1 in CH2Cl2 is substantially changed. Among the tetrabutylammonium (TBA) salts we tested, including F- OH- (from TBAOH in MeOH), Cl-, Br-, I-, OAc-, HSO4-, TsO- (Et4N salt), and H2PO4-, F- was found to be the most effective fluorescence quencher. Quantitative fluorescence analysis of the titration data revealed that the anions are classified into two categories: (1) Simple mono-anions, such as F- (log beta(F)(2) = 11.00 +/- 0.08), OH- (log beta(OH)(2) = 9.05 +/- 0.01), and Cl- (log beta(2) = 9.96 +/- 0.70) that follow the stoichiometry of 1:2, indicating the formation of (1.X-2)(2-) complexes; (2) Oxo-anions, such as OAc- (log beta(OAc)(1) = 5.13 +/- 0.012), H2PO4- (log beta(HP)(1) = 4.87 +/- 0.03), and TsO- (using tetraethylammonium salt, (log beta(OTs)(1) = 3.36 +/- 0.02) that show the stoichiometry of 1:1, indicating the formation of (1.X)(-) complexes. The complexation behaviors were further confirmed by H-1 NMR spectroscopy. In the co-crystal prepared from 1,1-binaphthy1-2,2'-diol (BINOL) and Et4NF, F- and BINOL are assembled to form a linear polymeric array, with a dimeric group of BINOL/BINOL anions linked as the side-chains. Intramolecular hydrogen bond was observed within the BINOL anion. This provides structural insights about the BINOL-fluoride complex formation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.047