N.N'-Dibenzoyl-1.2-diamino-anthrachinon | 56250-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N.N'-Dibenzoyl-1.2-diamino-anthrachinon
• 英文别名: 1,2-bis-benzoylamino-anthraquinone；1.2-Bis-benzamino-anthrachinon；1,2-Bis-benzoylamino-anthrachinon；N-(1-benzamido-9,10-dioxoanthracen-2-yl)benzamide
• CAS: 56250-76-1
• 化学式: C₂₈H₁₈N₂O₄
• 分子量: 446.462
• InChiKey: OMFLKLGIPMIASU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N.N'-Dibenzoyl-1.2-diamino-anthrachinon 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以62%的产率得到2-phenyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  Colorimetric and Ratiometric Fluorescence Sensing of Fluoride:  Tuning Selectivity in Proton Transfer

  摘要：

  [GRAPHICS]Phenyl-1H-anthra[1,2-d]imidazole-6,11-dione (1) and its derivatives (2 and 3) have been investigated 14 as new colorimetric and ratiometric fluorescent chemosensors for fluoride. Acute spectral responses of 1 and 3 to fluoride in acetonitrile have been observed: an approximately 100 nm red shift in absorption and fluorescence emission and a very large ratiometric fluorescent response (R-max/R-min is 88 for sensor 1 and 548 for sensor 3). From the changes in the absorption, fluorescence, and H-1 NMR titration spectra, proton-transfer mechanisms have been deduced. In ground states, a two-step process has been observed: first, the formation of the sensor-fluoride hydrogen-bond complex [(LHF)-F-...](-) and then the fluoride-induced deprotonation of the complex to form L- and FHF-. In excited states, the excited-state intermolecular proton-transfer made a contribution to the deprotonation. The selectivity for F- can be tuned by electron push-pull properties of the substituents on the phenyl para position of the sensors. Sensor 1 shows the best selectivity. The excellent selectivity of 1 for F- is attributed to the fitness in the acidity of its NH-group, which is tuned to be able to distinguish the subtle difference in the affinity of F-, CH3CO2-, and H2PO4- to proton.

  DOI：

  10.1021/jo051766q
• 作为产物：
  描述：

  1,2-二氨基蒽醌 、 苯甲酰氯 在 2,3-二甲基苯胺 作用下， 生成 N.N'-Dibenzoyl-1.2-diamino-anthrachinon
  参考文献：
  名称：

  Battegay; Claudin, Bulletin de la Societe Chimique de France, 1921, vol. <4> 29, p. 1021

  摘要：

  DOI：

文献信息

• Battegay; Claudin, Bulletin de la Societe Chimique de France, 1921, vol. <4> 29, p. 1021
  作者：Battegay、Claudin

  DOI：——

  日期：——
• LOSKUTOV V. A.; KRUGLYAK T. I.; KONSTANTINOVA A. V.; FOKIN E. P., IZV. SIB. OTD. AN CCCP <IZSK-AV>, 1975, HO 4, CEP. XIM. N. VYP. 2, 128-13+
  作者：LOSKUTOV V. A.、 KRUGLYAK T. I.、 KONSTANTINOVA A. V.、 FOKIN E. P.

  DOI：——

  日期：——
• US4520072A
  申请人：——

  公开号：US4520072A

  公开（公告）日：1985-05-28
• Colorimetric and Ratiometric Fluorescence Sensing of Fluoride:  Tuning Selectivity in Proton Transfer
  作者：Xiaojun Peng、Yunkou Wu、Jiangli Fan、Maozhong Tian、Keli Han

  DOI：10.1021/jo051766q

  日期：2005.12.1

  [GRAPHICS]Phenyl-1H-anthra[1,2-d]imidazole-6,11-dione (1) and its derivatives (2 and 3) have been investigated 14 as new colorimetric and ratiometric fluorescent chemosensors for fluoride. Acute spectral responses of 1 and 3 to fluoride in acetonitrile have been observed: an approximately 100 nm red shift in absorption and fluorescence emission and a very large ratiometric fluorescent response (R-max/R-min is 88 for sensor 1 and 548 for sensor 3). From the changes in the absorption, fluorescence, and H-1 NMR titration spectra, proton-transfer mechanisms have been deduced. In ground states, a two-step process has been observed: first, the formation of the sensor-fluoride hydrogen-bond complex [(LHF)-F-...](-) and then the fluoride-induced deprotonation of the complex to form L- and FHF-. In excited states, the excited-state intermolecular proton-transfer made a contribution to the deprotonation. The selectivity for F- can be tuned by electron push-pull properties of the substituents on the phenyl para position of the sensors. Sensor 1 shows the best selectivity. The excellent selectivity of 1 for F- is attributed to the fitness in the acidity of its NH-group, which is tuned to be able to distinguish the subtle difference in the affinity of F-, CH3CO2-, and H2PO4- to proton.