1,4-bis(triphenylethenyl)benzene | 134868-89-6

• 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: 1,4-bis(triphenylethenyl)benzene
• 英文别名: 1,4-bis(1,2,2-triphenylethenyl)benzene；1,4-bis(1,2,2-triphenylvinyl)benzene；1-[4-(1,2,2-triphenylvinyl)phenyl]-1,2,2-triphenylethene；Benzene, 1,4-bis(triphenylethenyl)-
• CAS: 134868-89-6
• 化学式: C₄₆H₃₄
• 分子量: 586.776
• InChiKey: JPZVDFIVMYLKOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  7.0
• 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：

  1,4-bis(triphenylethenyl)benzene 在 iron(III) chloride 、 硝基甲烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 1,4-bis(10-phenylphenanthren-9-yl)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：

  1,1,2,2-四苯乙烯 在 二硫化碳 、 aluminum (III) chloride 、 diphenylmethyllithium 作用下， 以 四氢呋喃 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

文献信息

• 新規なトリボリルアルケン、その製造方法、及び多置換アルケンの製造方法
  申请人：学校法人明治大学

  公开号：JP2020007232A

  公开（公告）日：2020-01-16

  【課題】 医薬品や電子材料として有用なテトラアリールアルケンの合成中間体となる化合物を提供する。【解決手段】 一般式(I)〔式中、Ｒａは、置換基を有していてもよいアリール基などを表す。〕で表されるトリボリルアルケン。【選択図】 なし

  提供一种作为药品和电子材料中间体的有用四芳基烯烃化合物的合成中间体。一般式(I)中，Ra代表可具有取代基的芳基等。
• Stepwise Suzuki−Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl−B(dan)s: Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes
  作者：Tomohiro Tani、Naomi Takahashi、Yuuki Sawatsugawa、Mana Osano、Teruhisa Tsuchimoto

  DOI：10.1002/adsc.202001116

  日期：2021.4.27

  tetrasubstituted alkenes with desired carbon frameworks at desired positions can be prepared in high yields. For example, an alkene with four distinct aryl groups, p‐MeOC6H4, p‐CF3C6H4, p‐MeC6H4, and p‐NCC6H4, was obtained in 71% overall yield via six steps, starting with the dehydrogenative borylation of p‐MeC6H4C≡CH with HB(dan). Moreover, a variety of tetrasubstituted alkenes, including regio‐

  合成了具有三个不同反应性的硼烷基的烯烃，然后逐步与芳基卤化物进行区域选择性交联，得到四取代的烯烃。关键的三硼烷基烯烃衍生自乙炔基B（dan）s与B 2（pin）2的铂催化二硼酸酯化反应。由于从炔基-B（dan）s开始的每个步骤都具有出色的区域选择性和反应效率，因此可以高收率制备在所需位置具有所需碳骨架的四取代烯烃。例如，具有四个不同芳基的烯烃，p- MeOC 6 H 4，p- CF 3 C 6 H 4，p-MeC 6 ħ 4，和p -NCC 6 ħ 4，经六个步骤以71％的总产率获得，先从的脱氢硼化p -MeC 6 ħ 4 C≡CH与HB（旦）。此外，通过制定的策略可以使用多种四取代烯烃，包括上述四芳基烯烃的区域和立体异构体，AIE活性TPTPE及其衍生物，以及著名的乳腺癌药物（Z）-他莫昔芬。
• Efficient Light Emitters in the Solid State: Synthesis, Aggregation-Induced Emission, Electroluminescence, and Sensory Properties of Luminogens with Benzene Cores and Multiple Triarylvinyl Peripherals
  作者：Carrie Y. K. Chan、Zujin Zhao、Jacky W. Y. Lam、Jianzhao Liu、Shuming Chen、Ping Lu、Faisal Mahtab、Xiaojun Chen、Herman H. Y. Sung、Hoi Sing Kwok、Yuguang Ma、Ian D. Williams、Kam Sing Wong、Ben Zhong Tang

  DOI：10.1002/adfm.201102030

  日期：2012.1.25

  Benzene‐cored luminogens with multiple triarylvinyl units are designed and synthesized. These propeller‐shaped molecules are nonemissive when dissolved in good solvents, but become highly emissive when aggregated in poor solvents or in the solid state, showing the novel phenomenon of aggregation‐induced emission. Restriction of intramolecular motion is identified as the main cause for this effect.

  设计并合成了具有多个三芳基乙烯基单元的以苯为核心的发光剂。这些螺旋桨状分子在溶解于良溶剂中时不会发光，但在不良溶剂中或以固态聚集时会变得高度发光，显示出聚集诱导发射的新现象。限制分子内运动被​​认为是造成这种作用的主要原因。凭借其高的固态荧光量子产率（高达1）以及高的热稳定性和形态稳定性，以发光剂为发光体的发光二极管以高亮度和10800 cd m的效率发出天蓝色至绿蓝色光- 2，5.8光盘-1和2.7％。发光剂的纳米聚集体的发射可以通过苦味酸进行指数猝灭，或者通过Ru 3+进行选择性猝灭，猝灭常数分别高达10 5和〜2.0×10 5 L mol -1，使其高度敏感（并具有选择性）。 ）爆炸物和金属离子的化学传感器。
• Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads
  作者：Moloy Banerjee、Susanna J. Emond、Sergey V. Lindeman、Rajendra Rathore

  DOI：10.1021/jo701474y

  日期：2007.10.1

  [GRAPHICS]We have demonstrated that reactions of diphenylmethyllithium with a variety of substituted benzophenones produces corresponding tertiary alcohols that are easily dehydrated, without any need for purification, to produce various unsymmetrical and symmetrical tetraarylethylenes in excellent yields. The simplicity of the method allows for the preparation of a variety of ethylenic derivatives in multigram (10-50 g) quantities with great ease. The methodology was successfully employed for the preparation of various triphenylethylene (TPE)-based triads (i.e., TPE-spacer-TPE) containing polyphenylene and fluoranyl-based spacers. The ready availability of various substituted tetraarylethylenes allowed us to shed light on the effect of substituents on the oxidation potentials (E-ox) of various tetraarylethylenes. Moreover, the electronic coupling among the triphenylethylene moieties in various TPE-spacer-TPE triads was briefly probed by electrochemical and optical methods.
• 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.