2-biphenyl-4-yl-1,1-diphenyl-ethene | 125643-81-4

• 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: 2-biphenyl-4-yl-1,1-diphenyl-ethene
• 英文别名: 4-(2,2-diphenylvinyl)-1,1'-biphenyl；1,1-Diphenyl-2-biphenylylethylen；4-(2,2-diphenylvinyl)biphenyl；2-Biphenyl-4-yl-1,1-diphenyl-aethen；1-(2,2-diphenylethenyl)-4-phenylbenzene
• CAS: 125643-81-4
• 化学式: C₂₆H₂₀
• 分子量: 332.445
• InChiKey: KRUBKGBBJQSCEM-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  468.1±35.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 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：

  2-biphenyl-4-yl-1,1-diphenyl-ethene 在 sodium hypochlorite 、 palladium on activated charcoal 、 4-苯基吡啶-N-氧化物 、 甲烷磺酸 、 (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) 、 lithium perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 26.5h， 生成 (R)-2-amino-2-biphenyl-1,1-diphenylethanol
  参考文献：
  名称：

  对映体纯形式的重取代1,2-氨基醇的合成

  摘要：

  提出了一种简单，方便的方法来制备光学纯的2-氨基-2-芳基-1,1-二苯基乙醇。发现烯丙胺以区域选择性和立体特异性方式产生三芳基氧杂环戊烷的开环。除去烯丙基保护基提供了对映体纯形式的游离1，2-氨基醇。

  DOI：

  10.1021/jo050960+
• 作为产物：
  描述：

  在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2-biphenyl-4-yl-1,1-diphenyl-ethene
  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

文献信息

• Pd-Catalyzed C═C Double-Bond Formation by Coupling of <i>N</i>-Tosylhydrazones with Benzyl Halides
  作者：Qing Xiao、Jian Ma、Yang Yang、Yan Zhang、Jianbo Wang

  DOI：10.1021/ol901876w

  日期：2009.10.15

  Pd-catalyzed reaction of N-tosylhydrazones with benzyl halides affords di- and trisubstituted olefins in high yields with excellent stereoselectivity. This coupling reaction is supposed to proceed through a migratory insertion of Pd carbene species.

  N-甲苯磺酰基hydr与苄基卤化物的Pd催化反应以高收率和优异的立体选择性提供了二取代和三取代的烯烃。该偶联反应被认为是通过Pd卡宾物质的迁移插入而进行的。
• Electron Transfer-Induced Coupling of Haloarenes to Styrenes and 1,1-Diphenylethenes Triggered by Diketopiperazines and Potassium tert-Butoxide
  作者：Eswararao Doni、Shengze Zhou、John Murphy

  DOI：10.3390/molecules20021755

  日期：——

  The coupling of haloarenes to styrenes and 1,1-diarylethenes has been achieved with potassium tert-butoxide in the presence of N,N'-dialkyldiketopiperazines. In contrast to previously reported reactions where phenanthroline has been used to mediate the reactions, the use of diketopiperazines can lead to either 1,1,2-triarylethenes or 1,1,2-triarylethanes, depending on the conditions used.

  已成功实现卤代芳烃与苯乙烯和1,1-二芳基乙烯的耦合，反应条件为存在N,N'-二烷基二酮哌嗪的氢氧化钾叔丁基。与之前使用苯并喹啉介导反应的报道不同，使用二酮哌嗪可以根据所用条件生成1,1,2-三芳基乙烯或1,1,2-三芳基乙烷。
• Nickel-Catalyzed Cross-Coupling Reaction of Alkenyl Methyl Ethers with Aryl Boronic Esters
  作者：Toshiaki Shimasaki、Yuko Konno、Mamoru Tobisu、Naoto Chatani

  DOI：10.1021/ol901978e

  日期：2009.11.5

  The Ni(0)-catalyzed cross-coupling of alkenyl methyl ethers with boronic esters is described. Several types of alkenyl methyl ethers can be coupled with a wide range of boronic esters to give the stilbene derivatives.

  描述了Ni（0）催化的烯基甲基醚与硼酸酯的交叉偶联。几种类型的烯基甲基醚可以与各种硼酸酯偶联，得到二苯乙烯衍生物。
• Thianthrenium-Enabled Phosphorylation of Aryl C–H Bonds via Electron Donor–Acceptor Complex Photoactivation
  作者：Hao Xu、Xufeng Li、Yuzheng Dong、Shuangran Ji、Junze Zuo、Jian Lv、Daoshan Yang

  DOI：10.1021/acs.orglett.3c01303

  日期：2023.5.26

  An efficient strategy for the preparation of aryl phosphonates via blue-light-promoted single electron transfer process of an EDA complex between phosphites and thianthrenium salts has been demonstrated. The corresponding substituted aryl phosphonates were obtained in good to excellent yields, and the byproduct thianthrene can be recovered and reused in quantity. This developed method realizes the

  已经证明了通过亚磷酸盐和噻蒽盐之间的 EDA 络合物的蓝光促进单电子转移过程制备芳基膦酸盐的有效策略。相应的取代芳基膦酸酯以良好的收率获得，并且副产物噻蒽可以大量回收和再利用。该方法通过芳烃的间接C-H功能化实现了芳基膦酸酯的构建，在药物发现和开发中具有潜在的应用价值。
• Synthesis of gem-tetraphenylethylene oligomers utilizing Suzuki reaction and their aggregation properties
  作者：Debabrata Jana、Shatabdi Boxi、Binay K. Ghorai

  DOI：10.1016/j.dyepig.2013.07.008

  日期：2013.12

  Four new gem-tetraphenylethylene-based oligomers were synthesized by Suzuki coupling reaction in good yields (62-80%) and characterized by NMR, mass spectrometer and elemental analysis. The absorption maxima of the synthesized oligomers in the solution possess similar absorption bands located at 328-332 nm. They are shown to be thermally stable and emit light in blue region (404-485 nm). All the oligomers are AIE-active, emit weakly in solutions with Phi(f) values not exceeding 4%, become strong emitters in the aggregated states and the PL intensity values increase up to 18-fold. The results of CV measurements of the oligomers showed good reversibility, indicating that the compounds have good electrochemical stability. The HOMO values of the oligomers are in the range of -5.63 to -5.61 eV. The photoluminescence properties in aggregate-state and the high HOMO energy levels of these oligomers make them applicable as an active material for a light-emitting device. (C) 2013 Elsevier Ltd. All rights reserved.