4-(3-dibutylamino-phenylamino)-[1,2]naphthoquinone | 1253943-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(3-dibutylamino-phenylamino)-[1,2]naphthoquinone
• CAS: 1253943-34-8
• 化学式: C₂₄H₂₈N₂O₂
• 分子量: 376.499
• InChiKey: UGEAOTVEVIJONT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  m-dibutylaminoaniline 、 sodium 1,2-naphthoquinone-4-sulfonate 在 nickel(II) acetate tetrahydrate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 12.0h， 以5%的产率得到9-dibutylamino-7H-benzo[c]carbazole-5,6-dione
  参考文献：
  名称：

  Heterocyclic quinol-type fluorophores. Part 9: Effect of forming a continuous intermolecular hydrogen bonding chain between fluorophores on the solid-state fluorescence properties

  摘要：

  Three heterocyclic quinol-type fluorophores with benzo[c]carbazol-6-one skeleton or benzo[b]naphtho [1,2-d]furan-6-one skeleton, 9-dibutylamino-5-hydroxy-5-phenyl-5,7-dihydro-benzo[c]carbazol-6-one (5a), 7-butyl-9-dibutylamino-5-hydroxy-5-phenyl-5,7-dihydro-benzo[c]carbazol-6-one (5b) and 9-dibutylamino-5-hydroxy-5-phenyl-5H-benzo[b]naphtho[1,2-d]furan-6-one (6c) have been synthesized and their photophysical properties have been investigated in solution and in the solid state. The fluorescence quantum yield (Phi) increases in the order of 5b (0.35)<5a (0.41)<6c (0.74) in 1,4-dioxane. On the other hand, the Phi value in the solid state increases in the order of 5a<<6C (0.03)<5b (0.07), which are much smaller than those in 1,4-dioxane. To elucidate the effects of molecular and crystal structures on the solid-state fluorescence properties, we have performed the semi-empirical molecular orbital calculations (AM1 and INDO/S) and X-ray crystallographic analysis. It was found that the formation of a continuous intermolecular hydrogen bonding between adjacent fluorophores is observed in the crystal of 5a, which is considered to cause a drastic fluorescence quenching in the solid state. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.026