4-phenoxy-N-(2',6'-diisopropylphenyl)-1,8-naphthalimide | 1616788-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-phenoxy-N-(2',6'-diisopropylphenyl)-1,8-naphthalimide
• 英文别名: 2-[2,6-Di(propan-2-yl)phenyl]-6-phenoxybenzo[de]isoquinoline-1,3-dione；2-[2,6-di(propan-2-yl)phenyl]-6-phenoxybenzo[de]isoquinoline-1,3-dione
• CAS: 1616788-66-9
• 化学式: C₃₀H₂₇NO₃
• 分子量: 449.549
• InChiKey: JSUFHTAWUYYFSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 在 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-phenoxy-N-(2',6'-diisopropylphenyl)-1,8-naphthalimide
  参考文献：
  名称：

  Substituent effect on quantum efficiency in 4-aryloxy-N-(2′,6′-diisopropylphenyl)-1,8-naphthalimides: Experimental and computational investigations

  摘要：

  A series of potential optical brightening agents - 4-aryloxy-N-(2',6'-diisopropylpheny1)-1,8-naphthalimides are synthesized and their photo-physical properties are experimentally determined. Interestingly, it is found that their quantum efficiencies or quantum yields are exclusively dependent on the substituents on the aryloxy group at the 4-position. It is postulated that the electronic effect of the substituents influences the photo-induced electron transfer process, which causes a variation in quantum efficiencies. Due to analysis of charge transfer from 1,8-naphthalimide molecular part to its substituents in dichloromethane based on the time-dependent density functional theory at Becke 3-parameters Lee-Yang-Parr level coupling with the 6-31G(d) basis set in the conductor-like polarizable continuum model with the united atom topological model computations, it is found that computed charge transfers of these serial compounds correspond well with their experimental quantum yields. Validation of the calculation method is performed by experimental determination of the quantum yield of the nitro-substituted compound. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.05.007

文献信息

• Substituent effect on quantum efficiency in 4-aryloxy-N-(2′,6′-diisopropylphenyl)-1,8-naphthalimides: Experimental and computational investigations
  作者：Tianchai Choppawa、Mongkol Sukwattanasinitt、Somboon Sahasithiwat、Vithaya Ruangpornvisuti、Paitoon Rashatasakhon

  DOI：10.1016/j.dyepig.2014.05.007

  日期：2014.10

  A series of potential optical brightening agents - 4-aryloxy-N-(2',6'-diisopropylpheny1)-1,8-naphthalimides are synthesized and their photo-physical properties are experimentally determined. Interestingly, it is found that their quantum efficiencies or quantum yields are exclusively dependent on the substituents on the aryloxy group at the 4-position. It is postulated that the electronic effect of the substituents influences the photo-induced electron transfer process, which causes a variation in quantum efficiencies. Due to analysis of charge transfer from 1,8-naphthalimide molecular part to its substituents in dichloromethane based on the time-dependent density functional theory at Becke 3-parameters Lee-Yang-Parr level coupling with the 6-31G(d) basis set in the conductor-like polarizable continuum model with the united atom topological model computations, it is found that computed charge transfers of these serial compounds correspond well with their experimental quantum yields. Validation of the calculation method is performed by experimental determination of the quantum yield of the nitro-substituted compound. (C) 2014 Elsevier Ltd. All rights reserved.