N,N'-bis(2-hydroxybenzilidene)-2,4,6-trimethylbenzene-1,3-diamine | 294649-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N'-bis(2-hydroxybenzilidene)-2,4,6-trimethylbenzene-1,3-diamine
• 英文别名: N,N'-bis(2-hydroxybenzylidene)-2,4,6-trimethylbenzene-1,3-diamine；2,2'-{(2,4,6-trimethylbenzene-1,3-diyl)bis[nitrilo(E)methylylidene]}diphenol；2-[[3-[(2-hydroxyphenyl)methylideneamino]-2,4,6-trimethylphenyl]iminomethyl]phenol
• CAS: 294649-85-7
• 化学式: C₂₃H₂₂N₂O₂
• 分子量: 358.44
• InChiKey: ZGHDEPBPPHFQGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  zinc(II) nitrate hexahydrate 、 N,N'-bis(2-hydroxybenzilidene)-2,4,6-trimethylbenzene-1,3-diamine 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以76%的产率得到[(Zn(N,N'-bis(2-hydroxybenzylidene)-2,4,6-trimethylbenzene-1,3-diamine(2-)))2]
  参考文献：
  名称：

  Fluorescent Zinc(II) Complex Exhibiting “On-Off-On” Switching Toward Cu²⁺ and Ag⁺ Ions

  摘要：

  Binuclear zinc(II) and copper(II) complexes based on a new Schiff base ligand N,N'-bis(2-hydroxybenzilidene)-2,4,6-trimethylbenzene-1,3-diamine (H2L) have been synthesized. The ligand H2L and complexes under investigation have been characterized by elemental analyses, spectral (FT-IR H-1, C-13 NMR, ESI-MS, electronic absorption, emission), and electrochemical studies. The structures of H2L and complexes [{Zn(C23H18N2O2)}(2)] (1) and [{Cu(C23H18N2O2)}(2)]center dot H2O (2) have been determined crystallographically. Selective "On-Off-On" switching behavior of the fluorescent complex 1 has been studied. The fluorescence intensity of 1 quenches (turns-off) upon addition of Cu2+, while enhances (turns-on) in the presence of Ag+ ions. The mechanisms of "On-Off-On" signaling have been supported by H-1 NMR, ESI-MS, electronic absorption, and emission spectral studies. Job's plot analysis supported 1:1 and 1:2 stoichiometries for Cu2+ and Ag+ ions, respectively. Association and quenching constants have been estimated by the Benesi-Hildebrand method and Stern-Volmer plot. Moreover, 1 mimics a molecular keypad lock that follows correct chemical input order to give maximum output signal.

  DOI：

  10.1021/ic1018086
• 作为产物：
  描述：

  2,4,6-三甲基-1,3-苯二胺 、 水杨醛 以 甲醇 为溶剂， 反应 10.0h， 以70%的产率得到N,N'-bis(2-hydroxybenzilidene)-2,4,6-trimethylbenzene-1,3-diamine
  参考文献：
  名称：

  Fluorescent Zinc(II) Complex Exhibiting “On-Off-On” Switching Toward Cu²⁺ and Ag⁺ Ions

  摘要：

  Binuclear zinc(II) and copper(II) complexes based on a new Schiff base ligand N,N'-bis(2-hydroxybenzilidene)-2,4,6-trimethylbenzene-1,3-diamine (H2L) have been synthesized. The ligand H2L and complexes under investigation have been characterized by elemental analyses, spectral (FT-IR H-1, C-13 NMR, ESI-MS, electronic absorption, emission), and electrochemical studies. The structures of H2L and complexes [{Zn(C23H18N2O2)}(2)] (1) and [{Cu(C23H18N2O2)}(2)]center dot H2O (2) have been determined crystallographically. Selective "On-Off-On" switching behavior of the fluorescent complex 1 has been studied. The fluorescence intensity of 1 quenches (turns-off) upon addition of Cu2+, while enhances (turns-on) in the presence of Ag+ ions. The mechanisms of "On-Off-On" signaling have been supported by H-1 NMR, ESI-MS, electronic absorption, and emission spectral studies. Job's plot analysis supported 1:1 and 1:2 stoichiometries for Cu2+ and Ag+ ions, respectively. Association and quenching constants have been estimated by the Benesi-Hildebrand method and Stern-Volmer plot. Moreover, 1 mimics a molecular keypad lock that follows correct chemical input order to give maximum output signal.

  DOI：

  10.1021/ic1018086

文献信息

• Pandey, Rampal; Ribas, Joan; Corbella, Montserrat, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2011, vol. 50, # 9-10, p. 1450 - 1456
  作者：Pandey, Rampal、Ribas, Joan、Corbella, Montserrat、Shankar Pandey, Daya

  DOI：——

  日期：——