2,4,6-Tri[(5-thiophen-2-yl)-phenyl]-1,3,5-triazine | 1253123-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2,4,6-Tri[(5-thiophen-2-yl)-phenyl]-1,3,5-triazine
• 英文别名: 2,4,6-tri[p-(2-thienyl)-phenyl]-1,3,5-triazine；2,4,6-Tris(4-thiophen-2-ylphenyl)-1,3,5-triazine；2,4,6-tris(4-thiophen-2-ylphenyl)-1,3,5-triazine
• CAS: 1253123-32-8
• 化学式: C₃₃H₂₁N₃S₃
• 分子量: 555.748
• InChiKey: YATBVTZZJGPTMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(2-thienyl)benzonitrile 在 三氟甲磺酸 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以15%的产率得到2,4,6-Tri[(5-thiophen-2-yl)-phenyl]-1,3,5-triazine
  参考文献：
  名称：

  不同中心核星形噻吩衍生物电化学聚合聚合物/共聚物的电致变色性能

  摘要：

  Three star-shaped thiophene derivatives, namely TPAT, PHT and TPTT with different central cores of triphenylamine, phenyl and 2,4,6-triphenyl-1,3,5-triazine respectively, were synthesized and characterized. They were further successfully prepared into the corresponding cross-linked polymers pTPAT, pPHT and pTPTT via electrochemical polymerization. The cyclic voltammetry curves showed that pPHT and pTPTT displayed the relatively higher onset oxidative potentials than pTPAT. After being applied with the positive voltages in an electrochemical cell, pTPAT exhibited the obvious electrochromic behaviors, while such phenomenons were not observed in the case of pPHT and pTPTT. The theory calculation results together with the electrochemistry properties revealed that the electrochromism of pTPAT may mainly depend on its relatively lower oxidative potential because of the introduction of triphenylamine with low ionization energy. Through the copolymerization with 3,4-ethylenedioxythiophene (EDOT) which is also of relatively low ionization energy, pPHT-EDOT and pTPTT-EDOT both exhibited excellent electrochromic properties. The oxidative potential or ionization energy of polymer is thought to be one of the key factors determining the electrochromism. (C) 2017 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.0161706jes

文献信息

• Synthesis and electrochemical characterization of new optoelectronic materials based on conjugated donor–acceptor system containing oligo-tri(heteroaryl)-1,3,5-triazines
  作者：Krzysztof R. Idzik、Peter Rapta、Piotr J. Cywinski、Rainer Beckert、Lothar Dunsch

  DOI：10.1016/j.electacta.2010.03.076

  日期：2010.7

  A series of novel oligoarylenes based on donor–acceptor system, containing triazine moiety as an electron-transporting central core, have been prepared by electrochemical polymerization. The redox behaviour of poly(2,4,6-tri[p-(2-(3,4-ethylenedioxythienyl))-phenyl]-1,3,5-triazine) was studied by cyclic voltammetry and triple in situ ESR/UV–vis–NIR spectroelectrochemistry to get more details on the

  通过电化学聚合制备了一系列基于供体-受体体系的新型低聚亚芳基，其中含有三嗪部分作为电子传输的中心核。通过循环伏安法和三原位ESR /研究了聚（2,4,6-三[ p-（2-（3,4-乙撑二氧噻吩基））-苯基] -1,3,5-三嗪）的氧化还原行为。紫外-可见-近红外光谱电化学可以更详细地了解薄膜中载流子的类型。为了获得所需的低聚亚芳基，已经通过Stille交叉偶联方法合成了具有各种电致变色侧基的三嗪核心单体。结构已通过1 H NMR确证，1313 C NMR和元素分析。单体在常见的有机溶剂（如氯仿，二氯甲烷或甲苯）中显示出良好的化学稳定性，并且在宽温度范围内也显示出出色的热稳定性。此外，它们的光物理性质已经通过使用荧光光谱法得以确立。电化学结果以及荧光光谱表明，三嗪的这些衍生物可以成功地用于有机发光二极管（OLED）的制造中。
• Electrochromic Properties of Polymers/Copolymers via Electrochemical Polymerization Based on Star-Shaped Thiophene Derivatives with Different Central Cores
  作者：Weijun Li、Lan Chen、Yuyu Pan、Shuanma Yan、Yuyu Dai、Jin Liu、Yue Yu、Xingxing Qu、Qingbao Song、Mi Ouyang、Cheng Zhang

  DOI：10.1149/2.0161706jes

  日期：——

  Three star-shaped thiophene derivatives, namely TPAT, PHT and TPTT with different central cores of triphenylamine, phenyl and 2,4,6-triphenyl-1,3,5-triazine respectively, were synthesized and characterized. They were further successfully prepared into the corresponding cross-linked polymers pTPAT, pPHT and pTPTT via electrochemical polymerization. The cyclic voltammetry curves showed that pPHT and pTPTT displayed the relatively higher onset oxidative potentials than pTPAT. After being applied with the positive voltages in an electrochemical cell, pTPAT exhibited the obvious electrochromic behaviors, while such phenomenons were not observed in the case of pPHT and pTPTT. The theory calculation results together with the electrochemistry properties revealed that the electrochromism of pTPAT may mainly depend on its relatively lower oxidative potential because of the introduction of triphenylamine with low ionization energy. Through the copolymerization with 3,4-ethylenedioxythiophene (EDOT) which is also of relatively low ionization energy, pPHT-EDOT and pTPTT-EDOT both exhibited excellent electrochromic properties. The oxidative potential or ionization energy of polymer is thought to be one of the key factors determining the electrochromism. (C) 2017 The Electrochemical Society. All rights reserved.