7-butyl-9-dibutylamino-5-hydroxy-5-phenyl-5,7-dihydro-benzo[c]carbazol-6-one | 1253943-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-butyl-9-dibutylamino-5-hydroxy-5-phenyl-5,7-dihydro-benzo[c]carbazol-6-one
• 英文别名: 7-Butyl-9-(dibutylamino)-5-hydroxy-5-phenylbenzo[c]carbazol-6-one；7-butyl-9-(dibutylamino)-5-hydroxy-5-phenylbenzo[c]carbazol-6-one
• CAS: 1253943-36-0
• 化学式: C₃₄H₄₀N₂O₂
• 分子量: 508.704
• InChiKey: DMCVMJNAGQWIQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-butyl-9-dibutylamino-7H-benzo[c]carbazole-5,6-dione 、 苯基锂 在 水 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以12%的产率得到7-butyl-9-dibutylamino-5-hydroxy-5-phenyl-5,7-dihydro-benzo[c]carbazol-6-one
  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

文献信息

• Heterocyclic quinol-type fluorophores. Part 9: Effect of forming a continuous intermolecular hydrogen bonding chain between fluorophores on the solid-state fluorescence properties
  作者：Yousuke Ooyama、Saori Nabeshima、Toshiki Mamura、Haruka Egawa Ooyama、Katsuhira Yoshida

  DOI：10.1016/j.tet.2010.08.026

  日期：2010.10

  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.