phenyl(4-(1,2,2-triphenylvinyl)phenyl)methanone | 1221822-83-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: phenyl(4-(1,2,2-triphenylvinyl)phenyl)methanone
• 英文别名: 1-(4-phenylcarbonyl)-1,2,2-triphenylethylene；Phenyl-[4-(1,2,2-triphenylethenyl)phenyl]methanone；phenyl-[4-(1,2,2-triphenylethenyl)phenyl]methanone
• CAS: 1221822-83-8
• 化学式: C₃₃H₂₄O
• 分子量: 436.553
• InChiKey: LYFRAVWPUIOVOX-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  549.6±29.0 °C(predicted)
• 密度：
  1.137±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  phenyl(4-(1,2,2-triphenylvinyl)phenyl)methanone 在 diphenylmethyllithium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1,4-bis(triphenylethenyl)benzene
  参考文献：
  名称：

  Graphene-like Molecules Based on Tetraphenylethene Oligomers: Synthesis, Characterization, and Applications

  摘要：

  Graphene-like molecules were prepared by oxidative cyclodehydrogenation of tetraphenylethene(TPE) oligomers using iron(III) chloride as the catalyst under mild conditions. All the oxidized samples can be separated effectively from the stepwise ring-closing reaction that highly related to the reaction time. For example, the model compounds obtained from the stepwise cyclization reaction show a regular red-shift in UV/vis absorption and photoluminescence (PL) spectra. This result reveals that the molecular conjugation length will extend with the stepwise ring-closing reaction going on. Interestingly, we successfully obtained a series of colorful luminogens with blue, cyan, and green emission during this stepwise and accurate ring closing process. Cyclic voltammetry measurements taken give the corresponding band gap, which supports the results obtained from optical spectroscopy. For the strong intermolecular interaction, our graphene molecules can self-assemble to form a red-colored and hexagonal fiber. Furthermore, some molecules exhibit piezochromic luminescence. The PL emission of the molecules before and after oxidation can be dramatically quenched by picric acid through the electron transfer and/or energy transfer mechanism, enabling them to function as chemosensors for explosive detection. In addition, fluorescence cell imaging studies proved their potential biological application.

  DOI：

  10.1021/cm501590w
• 作为产物：
  描述：

  二苯甲酮 在 二硫化碳 、 aluminum (III) chloride 、 四氯化钛 作用下， 生成 phenyl(4-(1,2,2-triphenylvinyl)phenyl)methanone
  参考文献：
  名称：

  四苯乙烯修饰的 D-π-A 型二氰乙烯衍生物表现出聚集诱导发射和高对比度机械荧光变色

  摘要：

  基于合理的设计策略，结合吸电子二氰基乙烯单元和给电子四苯乙烯部分，我们成功合成了两个π-共轭分子和。根据光学研究和理论计算结果，它们具有高度扭曲的构象、D-A型分子结构和明确的分子内电荷转移（ICT）性质。此外，两个分子在较高的THF/水混合物（水分数）中表现出聚集诱导发射（AIE）特性。并对外力也表现出荧光响应。研磨前后两者的发光颜色均发生了较大变化。和 的最大发射波长分别红移 46 nm 和 33 nm，意味着高对比度机械荧光变色。值得注意的是，机械荧光变色过程还表现出良好的可逆性。 XRD实验表明，机械荧光变色机理源于固态分子堆积的变化。

  DOI：

  10.1016/j.molstruc.2024.138204

文献信息

• Aggregation Emission Properties of Oligomers Based on Tetraphenylethylene
  作者：Weizhi Wang、Tingting Lin、Min Wang、Tian-Xi Liu、Lulu Ren、Dan Chen、Shu Huang

  DOI：10.1021/jp911311j

  日期：2010.5.13

  A series of eight derivatives based on tetraphenylethylene were prepared, and two of these, i.e., 1,1-bis(4-phenylcarbony1)-2,2-diphenylethylene (2), 1,1,2,2-tetrakis(4-phenylcarbonyl)phenylethylene (4), were characterized crystallographically. Because the rigidity and steric hindrance in the molecular structure enhanced regularly from sample 5 to 8, UV-visible absorption and PL spectra of 5-8 show the transition from aggregation-induced emission (AIE) to aggregation-induced emission enhancement (AIEE) behavior. Solid fluorescence lifetime characterization shows that samples with less steric hindrance and more interaction in or between molecules will result in a short fluorescence lifetime. All samples 5-8 become more emissive when their chains are induced to aggregate by adding water into their acetonitrile solutions. Cyclic voltammetry measurements taken give the band gap of sample 5-8 as 2.88, 2.70, 2.56, and 2.43 eV, and theoretical calculations also support these bad gap results. Conformational simulations also suggest that the origin of transition from AIE to AIEE behavior is due to the restricted intramolecular rotations of the aromatic rings in samples.
• Graphene-like Molecules Based on Tetraphenylethene Oligomers: Synthesis, Characterization, and Applications
  作者：Ji Ma、Tingting Lin、Xiaoyong Pan、Weizhi Wang

  DOI：10.1021/cm501590w

  日期：2014.7.22

  Graphene-like molecules were prepared by oxidative cyclodehydrogenation of tetraphenylethene(TPE) oligomers using iron(III) chloride as the catalyst under mild conditions. All the oxidized samples can be separated effectively from the stepwise ring-closing reaction that highly related to the reaction time. For example, the model compounds obtained from the stepwise cyclization reaction show a regular red-shift in UV/vis absorption and photoluminescence (PL) spectra. This result reveals that the molecular conjugation length will extend with the stepwise ring-closing reaction going on. Interestingly, we successfully obtained a series of colorful luminogens with blue, cyan, and green emission during this stepwise and accurate ring closing process. Cyclic voltammetry measurements taken give the corresponding band gap, which supports the results obtained from optical spectroscopy. For the strong intermolecular interaction, our graphene molecules can self-assemble to form a red-colored and hexagonal fiber. Furthermore, some molecules exhibit piezochromic luminescence. The PL emission of the molecules before and after oxidation can be dramatically quenched by picric acid through the electron transfer and/or energy transfer mechanism, enabling them to function as chemosensors for explosive detection. In addition, fluorescence cell imaging studies proved their potential biological application.
• D-π-A type dicyanoethylene derivatives modified by tetraphenylethylene exhibiting aggregation-induced emission and high-contrast mechanofluorochromism
  作者：Jiayi Chen、Jiakang Sun、Yong Zhan、Xiaqian Lian、Siying Lu

  DOI：10.1016/j.molstruc.2024.138204

  日期：2024.8

  electron-withdrawing dicyanoethylene unit and electron-donating tetraphenylethylene moiety, we successfully synthesized two π-conjugated molecules and . According to the optical research and theoretical calculation results, they had highly distorted conformations, D-A type molecular structure and definite intramolecular charge transfer (ICT) properties. Moreover, two molecules and showed aggregation-induced emission

  基于合理的设计策略，结合吸电子二氰基乙烯单元和给电子四苯乙烯部分，我们成功合成了两个π-共轭分子和。根据光学研究和理论计算结果，它们具有高度扭曲的构象、D-A型分子结构和明确的分子内电荷转移（ICT）性质。此外，两个分子在较高的THF/水混合物（水分数）中表现出聚集诱导发射（AIE）特性。并对外力也表现出荧光响应。研磨前后两者的发光颜色均发生了较大变化。和 的最大发射波长分别红移 46 nm 和 33 nm，意味着高对比度机械荧光变色。值得注意的是，机械荧光变色过程还表现出良好的可逆性。 XRD实验表明，机械荧光变色机理源于固态分子堆积的变化。