4-chloro-N-(4'-methoxyphenyl)-1,8-naphthalimide | 94255-72-8

• 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-chloro-N-(4'-methoxyphenyl)-1,8-naphthalimide
• 英文别名: 4-chloro-N-(4'-methoxy)phenyl-1,8-NI；4-methoxyphenyl-4'-chloro-1,8-NI；6-chloro-2-(4-methoxy-phenyl)-benzo[de]isoquinoline-1,3-dione；6-chloro-2-(4-methoxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione；6-chloro-2-(4-methoxyphenyl)benzo[de]isoquinoline-1,3-dione
• CAS: 94255-72-8
• 化学式: C₁₉H₁₂ClNO₃
• mdl: MFCD00805183
• 分子量: 337.762
• InChiKey: MAOZIGNMTUPQNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-氯-1,8-萘二甲酸酐 、 甲氧苯胺 在 吡啶 作用下， 反应 12.0h， 生成 4-chloro-N-(4'-methoxyphenyl)-1,8-naphthalimide
  参考文献：
  名称：

  Frontier molecular orbital analysis of dual fluorescent dyes: predicting two-color emission in N-Aryl -1,8-naphthalimides

  摘要：

  合成了双取代 N-芳基-1,8-萘酰亚胺的 3 × 3 基质，用于评估和发现双荧光 (DF)。本研究中包含的矩阵元素基于作为跷跷板平衡光物理模型提出的预测模型。该模型可作为优化 N-苯基-1,8-萘二甲酰亚胺双荧光发射的指导，通过在 N-芳烃的 4 位和萘的 4'-位适当放置取代基戒指。各种溶剂下的稳态荧光研究表明，基质中的九种染料中有四种具有双荧光。为了提供模型的更定量描述，使用循环伏安实验来计算构成这些 DF 染料的芳香族成分的 HOMO/LUMO 能量，并为支持 S1 和 S2 激发态的潜在混合提供证据。考虑到预测激发态性质（例如分子荧光）的困难，发现 DF 的九个“命中”中的四个比率意味着该模型的原理证明，并且应该为未来 DF 1,8- 的合成提供合理的基础萘二甲酰亚胺系统。

  DOI：

  10.1039/c001912g

文献信息

• Discovery of dual fluorescent 1,8-naphthalimide dyes based on balanced seesaw photophysical model
  作者：Premchendar Nandhikonda、Michael P. Begaye、Zhi Cao、Michael D. Heagy

  DOI：10.1039/b911768g

  日期：——

  The 3 × 3 matrix elements included for the evaluation of dual fluorescence are based on a predictive model described as a ‘seesaw balanced’ photophysical model.

  用于评估双荧光的三×三矩阵元素基于被称为“跷跷板平衡”的光物理预测模型。
• [EN] FLUORESCENT NAPHTHALIMIDE POLYMERS AND SOLUTIONS THEREOF FOR SCALE CONTROL IN AQUEOUS SYSTEMS<br/>[FR] POLYMÈRES DE NAPHTALIMIDE FLUORESCENTS ET SOLUTIONS ASSOCIÉES POUR LUTTER CONTRE LE TARTRE DANS DES SYSTÈMES AQUEUX
  申请人：NOURYON CHEMICALS INT BV

  公开号：WO2020243168A1

  公开（公告）日：2020-12-03

  Disclosed are fluorescent water-soluble water treatment polymers suitable for use in scale inhibition in industrial water systems, the water treatment polymers comprising non-quaternized fluorescent naphthalimide derivative monomers. Also disclosed are methods of making the monomers, methods of making the polymers, methods of inhibiting scale in an industrial water system, and methods of using the polymers in coagulation and flocculation, and in cleaning applications.
• Frontier molecular orbital analysis of dual fluorescent dyes: predicting two-color emission in N-Aryl -1,8-naphthalimides
  作者：Premchendar Nandhikonda、Michael P. Begaye、Zhi Cao、Michael D. Heagy

  DOI：10.1039/c001912g

  日期：——

  A 3 × 3 matrix of disubstituted N-aryl-1,8-naphthalimides was synthesized for the evaluation and discovery of dual fluorescence (DF). The matrix elements included for this study were based on a predictive model that is proposed as a seesaw balanced photophysical model. This model serves as a guide to optimize the dual fluorescence emission from N-phenyl-1,8-naphthalimdes by appropriate placement of substituent groups at both the 4-position of the N-arene as well as the 4′-position of the naphthalene ring. Steady-state fluorescence studies under a variety of solvents indicate that four of the nine dyes in the matrix are dual fluorescent. To provide a more quantitative description of the model, cyclic voltammetry experiments were used to calculate HOMO/LUMO energies of the aromatic components that comprise these DF dyes and give evidence in support for potential mixing of S1 and S2 excited states. Given the difficulties in predicting excited state properties such as molecular fluorescence, this ratio of four out of nine “hits’ for discovering DF signifies proof of principle for this proposed model and should provide a rational basis for the synthesis of future DF 1,8-naphthalimide systems.

  合成了双取代 N-芳基-1,8-萘酰亚胺的 3 × 3 基质，用于评估和发现双荧光 (DF)。本研究中包含的矩阵元素基于作为跷跷板平衡光物理模型提出的预测模型。该模型可作为优化 N-苯基-1,8-萘二甲酰亚胺双荧光发射的指导，通过在 N-芳烃的 4 位和萘的 4'-位适当放置取代基戒指。各种溶剂下的稳态荧光研究表明，基质中的九种染料中有四种具有双荧光。为了提供模型的更定量描述，使用循环伏安实验来计算构成这些 DF 染料的芳香族成分的 HOMO/LUMO 能量，并为支持 S1 和 S2 激发态的潜在混合提供证据。考虑到预测激发态性质（例如分子荧光）的困难，发现 DF 的九个“命中”中的四个比率意味着该模型的原理证明，并且应该为未来 DF 1,8- 的合成提供合理的基础萘二甲酰亚胺系统。