tetraphenylethylene-d20 | 307514-65-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: tetraphenylethylene-d20
• 英文别名: TPE-d20；1,2,3,4,5-Pentadeuterio-6-[1,2,2-tris(2,3,4,5,6-pentadeuteriophenyl)ethenyl]benzene
• CAS: 307514-65-4
• 化学式: C₂₆H₂₀
• 分子量: 352.286
• InChiKey: JLZUZNKTTIRERF-LODXIBBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  tetraphenylethylene-d20 在 四(三苯基膦)钯 、 溴 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Hydrogen Isotope Effect Endows a Breakthrough in Photoluminescent Covalent Organic Frameworks

  摘要：

  DOI：

  10.1021/jacs.3c10511
• 作为产物：
  描述：

  氘代苯 在 盐酸 、 aluminum (III) chloride 、 草酰氯 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 tetraphenylethylene-d20
  参考文献：
  名称：

  非互穿单晶共价有机框架。

  摘要：

  共价有机骨架（COF）作为单晶的生长极具挑战性。开放结构的单晶COF的不可访问性阻止了对面向结构的应用程序的探索。在这里，我们首次报告了一种非互穿的单晶COF LZU-306，它具有仅通过共价组装构造的开放结构。LZU-306具有80％的高空隙体积，用于研究网状四苯乙烯（TPE）作为单个聚集诱导的发射部分的内在动力学。固态2 H NMR研究确定，在报告的病例中，TPE中苯环的旋转是最自由的， 在203 K时旋转至1.0×10 4 Hz至1.5×10 7 Hz在293 K时的水平。这项研究不仅探索了开放框架单晶生长的新范例，而且还提供了一个独特的基质分离平台，可以将功能性部分网状化为定义明确和分离的状态。

  DOI：

  10.1002/anie.202007230

文献信息

• Phenyl Ring Dynamics in a Tetraphenylethylene-Bridged Metal–Organic Framework: Implications for the Mechanism of Aggregation-Induced Emission
  作者：Natalia B. Shustova、Ta-Chung Ong、Anthony F. Cozzolino、Vladimir K. Michaelis、Robert G. Griffin、Mircea Dincă

  DOI：10.1021/ja306042w

  日期：2012.9.12

  Molecules that exhibit emission in the solid state, especially those known as aggregation-induced emission (AIE) chromophores, have found applications in areas as varied as light-emitting diodes and biological sensors. Despite numerous studies, the mechanism of fluorescence quenching in AIE chromophores is still not completely understood. To this end, much interest has focused on understanding the low-frequency vibrational dynamics of prototypical systems, such as tetraphenylethylene (TPE), in the hope that such studies would provide more general principles toward the design of new sensors and electronic materials. We hereby show that a perdeuterated TPE-based metal-organic framework (MOF) serves as an excellent platform for studying the low-energy vibrational modes of AIE-type chromophores. In particular, we use solid-state H-2 and C-13 NMR experiments to investigate the phenyl ring dynamics of TPE cores that are coordinatively trapped inside a MOF and find a phenyl ring flipping energy barrier of 43(6) kJ/mol. DFT calculations are then used to deconvolute the electronic and steric contributions to this flipping barrier. Finally, we couple the NMI: and DFT studies with variable-temperature X-ray diffraction experiments to propose that both the ethylenic C=C bond twist and the torsion of the phenyl rings are important for quenching emission in TPE, but that the former may gate the latter. To conclude, we use these findings to propose a set of design criteria for the development of tunable turn-on porous sensors constructed from AIE-type molecules, particularly as applied to the design of new multifunctional MOFs.