4-(4'-vinylstyryl)benzaldehyde | 288105-09-9

• 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: 4-(4'-vinylstyryl)benzaldehyde
• 英文别名: 4-[(1E)-2-(4-ethenylphenyl)ethenyl]benzaldehyde；(E)-4-(4-vinylstyryl)benzaldehyde；4-[(E)-2-(4-ethenylphenyl)ethenyl]benzaldehyde
• CAS: 288105-09-9
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: OPDFGHNJTLBRBU-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• 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：

  4-(4'-vinylstyryl)benzaldehyde 在 palladium diacetate 、 四丁基溴化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.0h， 生成 4-(4'-(3'',5''-di-tert-butylstyryl)styryl)stilbene
  参考文献：
  名称：

  Synthesis, Morphology, and Optical Properties of Tetrahedral Oligo(phenylenevinylene) Materials

  摘要：

  A novel topological strategy is described for designing amorphous molecular solids suitable for optoelectronic applications. In this approach, chromophores are attached to a tetrahdral point of convergence. Stilbenoid units were covalently linked to tetraphenylmethane, tetraphenyladamantane, or tetraphenylsilane cores using palladium catalyzed coupling methodology, Thus, reaction of E(C6H5X)(4) (E = C and adamantane, X = I; E = Si, X = Br) with styrene or 4,3'-tert-butylvinylstilbene under Heck coupling conditions yields the corresponding tetrakis(stillbenyl) (E(STB)(4)) and tetrakis(4-tert-butyIstyrylstilbenyl) (E((BuSSB)-Bu-t)(4)) compounds. Similarly, reaction of 1,1-diphenyl-2-(4-dihydroxyboronphenyl)ethene or 2-(4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile with tetrakis(4-bromophenyl)methane using Suzuki coupling methodology gives tetrakis(4,4'-(2,2-diphenyl-vinyl)-1,1'-biphenyl (C(DPVBi)(4)) or tetrakis(4,4'-(3,3-diphenylacrylonitrile biphenyl)methane (C(DPAB)(4)), respectively, in good yields. Compounds with more extended conjugation can also be prepared. Thus, reaction of excess 1-(4'-tert-butylstyryl)-4-(4'-vinylstyryl)benzene with C(C6H4I)(4) provides tetrakis(4-(4'-(4"-tert-butylstyryl)styryl)stilbenyl)methane (C(4R-Bu-t)(4)) in low yield (similar to 20%). The more soluble analogue, tetrakis(4-(4'-(3",5"-di-tert-butylstyryl)stilbenyl)methane (C(4R-2(t)Bu)(4)) is prepared similarly using 1-(3',5'-di-tert-butylstyryl)-4-(4'-vinylstyryl)benzene and in better yield (similar to 80%). Alkoxy substituents can also be used to increase solubility. Tetrakis((4-(2',5'-dioctyloxy-4'-styryl)styryl)stilbenyl)methane methane, C(4R-(OC8H17)(2))(4), was prepared by treatment of C(C6H4I)(4) with excess 2,5-dioctyloxy-1-styryl-4(4'-vinylstyryl)benzene (yield similar to 73%). The simple stilbenyl-derivatives were found by DSC measurements and powder diffraction experiments to be crystalline compounds. Comparison of single-crystal X-ray diffraction data shows that C(STB)(4) and Si(STB)(4) form isomorphous crystals. The larger E((BuSSB)-Bu-t)4, C(DPVBi)(4), and C(DPAB)(4) compounds readily form amorphous glasses with elevated glass transition temperatures (T-g = 142-190 degrees C) in the absence of solvent. Extending the conjugation length of the arm leads to more stable glasses. For example, the glass transition temperature of C(4R-Bu-t)(4) was measured at 230 degrees C. Solution phase optical spectroscopic data of E((BuSSB)-Bu-t)(4) (E = C, adamantane, and Si) are characteristic of the parent distyrylbenzene chromophore. Films, however, show broad and significantly red-shifted emission spectra. In contrast, C(DPVBi)(4) gives absorption and emission spectra which are nearly identical between dilute solution phase samples and neat solid films. The emission of C(DPAB)(4) is broad and structureless, reminiscent of exciplex or excimer emission. Films of the tetramers with longer arms (C(4R-Bu-t)(4), C(4R-2(t)Bu)(4), and C(4R-(OC8H17)(2))(4)) show emission properties which are dependent on sample history. Annealing the sample at elevated temperature leads to red-shifted emission as a result of better interdigitation between the optically active fragments.

  DOI：

  10.1021/ja992924w
• 作为产物：
  描述：

  1,3-二噁戊环,2-(4-碘苯基)- 在 potassium phosphate 、 potassium tert-butylate 、 palladium diacetate 、 对甲苯磺酸 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 48.5h， 生成 4-(4'-vinylstyryl)benzaldehyde
  参考文献：
  名称：

  醛类二苯乙烯基苯：水中的胺识别

  摘要：

  水的变化：醛取代的水溶性二苯乙烯基苯的水溶液与胺反应，生成的亚胺或缩醛胺的荧光发生了显着变化。这种方法可以检测和识别水中的胺（见图）。

  DOI：

  10.1002/chem.201200930

文献信息

• Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions
  作者：Esmaeil Niknam、Farhad Panahi、Ali Khalafi-Nezhad

  DOI：10.1016/j.jorganchem.2020.121676

  日期：2021.3

  using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template

  基于钯部分固定在N上的非均相钯催化剂体系-杂环卡宾（NHC）改性的金属有机骨架（MOF）被开发用于Heck和无铜Sonogashira偶联反应。为了制备该催化剂体系，首先，通过后合成修饰（PSM）方法用NHC部分将MIL-101（Cr）官能化，然后将Pd金属稳定在预先制成的MIL-101（Cr）-NHC基底上。使用多种显微镜和光谱技术对该材料进行了表征，然后将其用作Heck和无铜Sonogashira反应中的高效多相Pd催化剂体系。非均质性测试结果表明，Pd-NHC-MIL-101（Cr）催化剂能够有效地异质催化这些偶联反应，并且在反应过程中未观察到MIL-101（Cr）模板的形态和​​结构发生明显变化。也，TEM和XPS分析证实了固定在MOF结构上的钯纳米粒子的存在证实了Pd的氧化态。在正常条件下，使用这种非均相钯催化剂体系，可以以高至极好的收率合成各种烯烃和炔烃衍生物。更重要的是，Pd
• Efficient nickel(<scp>ii</scp>) naringenin-oxime complex catalyzed Mizoroki–Heck cross-coupling reaction in the presence of hydrazine hydrate
  作者：Jin-Yi Song、Yang Liu、Hong-Yan Zhao、Hua-Tao Han、Zhuo-Fei Li、Wei-Hao Guo、Wen-Yi Chu、Zhi-Zhong Sun

  DOI：10.1039/c7nj03148c

  日期：——

  A novel nickel(II) naringenin-oxime complex was designed, synthesized and characterized. Therein, nickel(II) naringenin oxime complex as an efficient catalyst was used in Mizoroki-Heck coupling reactions of aryl halides adhering electron-rich and electron-deficient substituents with styrene, methyl acrylate and divinylbenzene (DVB), respectively. The reaction proceeded efficiently under the alkaline

  设计，合成和表征了新型的柚皮苷镍-肟复合物。其中，镍（II）柚皮素肟配合物作为有效催化剂，分别用于粘附富电子和缺电子取代基的芳基卤化物分别与苯乙烯，丙烯酸甲酯和二乙烯基苯（DVB）的Mizoroki-Heck偶联反应中。在碱性条件下，在0.30 mol％Ni（II）柚皮素肟肟络合物，N2H4•H2O作为还原剂在80°C的EtOH中有效地进行了反应，提供了30种烯烃产物，中等至极好的收率，其中包含四种新产物。烯烃 新的催化体系不仅提供了一种廉价，高效，绿色的工艺方法，而且扩大了反应范围。
• Soluble tetrahedral compounds for use in electroluminescent devices
  申请人：——

  公开号：US20030055278A1

  公开（公告）日：2003-03-20

  Electroluminescent compounds, devices and methods for making the foregoing are disclosed, which employ a novel topological strategy for designing amorphous molecular solids suitable for forming thin films in optoelectronic devices. In this approach chromophores are attached to a tetrahdral point of convergence.

  揭示了用于制造电致发光化合物、器件和方法，采用了一种新颖的拓扑策略，用于设计适用于在光电子器件中形成薄膜的非晶态分子固体。在这种方法中，色团被连接到四面体的汇聚点。
• US6824890B2
  申请人：——

  公开号：US6824890B2

  公开（公告）日：2004-11-30
• [EN] SOLUBLE TETRAHEDRAL COMPOUNDS FOR USE IN ELECTROLUMINESCENT DEVICES<br/>[FR] COMPOSES TETRAHEDRIQUES SOLUBLES DESTINES A ETRE UTILISES DANS DES DISPOSITIFS ELECTROLUMINESCENTS
  申请人：UNIV CALIFORNIA

  公开号：WO2001083410A1

  公开（公告）日：2001-11-08

  Electroluminescent compounds, devices and methods for making the foregoing are disclosed, which employ a novel topological strategy for designing amorphous molecular solids suitable for forming thin films in optoelectronic devices. In this approach chromophores are attached to a tetrahdral point of convergence.