tetrakis(4-carboxyphenyl)ethylene-d16 | 1397939-17-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tetrakis(4-carboxyphenyl)ethylene-d16
• 英文别名: H4TCPE-d16；2,3,5,6-Tetradeuterio-4-[1,2,2-tris(4-carboxy-2,3,5,6-tetradeuteriophenyl)ethenyl]benzoic acid；2,3,5,6-tetradeuterio-4-[1,2,2-tris(4-carboxy-2,3,5,6-tetradeuteriophenyl)ethenyl]benzoic acid
• CAS: 1397939-17-1
• 化学式: C₃₀H₂₀O₈
• 分子量: 524.357
• InChiKey: MPYOMTPWHUPLKU-NYCJPCIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N-二乙基甲酰胺 、 zinc nitrate hexahydrate 、 tetrakis(4-carboxyphenyl)ethylene-d16 以 乙醇 为溶剂， 反应 72.0h， 生成 Zn2(TCPE-d16)*(DEF)2*2DEF
  参考文献：
  名称：

  Phenyl Ring Dynamics in a Tetraphenylethylene-Bridged Metal–Organic Framework: Implications for the Mechanism of Aggregation-Induced Emission

  摘要：

  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.

  DOI：

  10.1021/ja306042w
• 作为产物：
  描述：

  氘代苯 在 溴 、 四氯化钛 、 potassium hydroxide 、 锌 作用下， 以 四氢呋喃 、 二硫化碳 、 N,N-二甲基甲酰胺 为溶剂， 生成 tetrakis(4-carboxyphenyl)ethylene-d16
  参考文献：
  名称：

  Phenyl Ring Dynamics in a Tetraphenylethylene-Bridged Metal–Organic Framework: Implications for the Mechanism of Aggregation-Induced Emission

  摘要：

  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.

  DOI：

  10.1021/ja306042w

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.