dimethyl pyrene-1,6-dicarboxylate | 29556-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: dimethyl pyrene-1,6-dicarboxylate
• CAS: 29556-79-4
• 化学式: C₂₀H₁₄O₄
• 分子量: 318.329
• InChiKey: SCWCBWXJSFHLEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  pyrene-1,6-dicarbonitrile 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 dimethyl pyrene-1,6-dicarboxylate
  参考文献：
  名称：

  酯官能化芘衍生物：酯取代基对光物理、电化学、电致变色和电致荧光变色性能的影响

  摘要：

  多功能电致变色材料广泛应用于光电器件. 芘是具有荧光特性的富π电子基团。酯官能化芘衍生物可能具有有趣的多功能特性，例如电致变色和电致荧光变色特性。在这项工作中，合成了单、二、三和四酯取代的芘衍生物，并研究了酯取代基的数量对其光物理、电化学、电致变色和电致荧光变色性能的影响。酯取代基的数量显着影响这些性质。芘上酯取代基数量的增加导致吸收和发射光谱的红移、驱动电压的降低以及电致变色的变化有色状态和电致变色性能。单酯、双酯和三酯官能化芘衍生物显示出良好的电致变色性能，即良好的开关稳定性、高光学对比度、快速响应和高着色效率。单酯和三酯官能化芘具有良好的电致荧光变色性能，在电致变色过程中具有可逆的荧光猝灭 - 有色和漂白状态之间的荧光恢复。酯官能化芘衍生物成功地用于两种色彩鲜艳的功能性数字显示器。这些结果表明，具有良好电致变色和电致荧光变色性能的酯官能化芘衍生物有望用于各种应用，例如数字显示器、有机

  DOI：

  10.1016/j.dyepig.2022.110203

文献信息

• 1-, 3-, 6-, and 8-Tetrasubstituted Asymmetric Pyrene Derivatives with Electron Donors and Acceptors: High Photostability and Regioisomer-Specific Photophysical Properties
  作者：Yosuke Niko、Shunsuke Sasaki、Kaishi Narushima、Dharmendar Kumar Sharma、Martin Vacha、Gen-ichi Konishi

  DOI：10.1021/acs.joc.5b01987

  日期：2015.11.6

  The systematic synthesis of five 1-, 3-, 6-, and 8-tetrasubstituted asymmetric pyrenes with electron donor and acceptor moieties is presented, together with an examination of their photophysical properties. Pyrene derivative PA1, containing one formyl and three piperidyl groups, showed bright solvatochromic fluorescence from green (lambda(em) = 557 nm, Phi(FL) = 0.94 in hexane) to red (lambda(em) = 648 nm, Phi(FL) = 0.50 in methanol), suggesting potential applications for PA1 as an environmentally responsive probe. Although the synthesis of simple 1- and 3-disubstituted pyrene derivatives is considered difficult, PA13, with two formyl groups at the 1- and 3-positions and two piperidyl groups at the 6- and 8-positions, could be synthesized successfully. PA13 exhibited less pronounced solvatochromism, but displayed a narrow fluorescent band with high Phi(FL) in all solvents (Phi(FL) > 0.75). Moreover, its absorption band displayed an exceptional bathochromic shift compared to the other derivatives (e.g., lambda(abs) = 480 and 522 nm in ethanol for PA1 and PA13, respectively), suggesting that such modifications of pyrene may be quite important for the modulation of its energy gap. Additionally, all compounds exhibited exceptionally high photostability, which highlights the advantage of these new dyes and provides new insights on the design of photostable fluorophores.