tetrastilbenylmethane | 205105-80-2

• 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: tetrastilbenylmethane
• 英文别名: 1-[(E)-2-phenylethenyl]-4-[tris[4-[(E)-2-phenylethenyl]phenyl]methyl]benzene
• CAS: 205105-80-2
• 化学式: C₅₇H₄₄
• 分子量: 728.976
• InChiKey: DVQMJNAHDGSOBU-OBCUGYALSA-N

物化性质

• 沸点：
  816.9±60.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  57
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.02
• 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：

  tetrastilbenylmethane 在 碘 、 氧气 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以16%的产率得到tetrakis(phenanthren-3-yl)methane
  参考文献：
  名称：

  The First Synthesis and Electronic Properties of Tetrakis[(hetero)phenanthrenyl]methanes

  摘要：

  DOI：

  10.1002/1099-0690(200207)2002:14<2269::aid-ejoc2269>3.0.co;2-e
• 作为产物：
  描述：

  4,4,4,4-甲乙烷四基四苯胺 在 盐酸 、 palladium diacetate 、 氟硼酸钠 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 tetrastilbenylmethane
  参考文献：
  名称：

  Fourfold Heck reactions on the tetraphenylmethane tripod: Model studies towards construction of centrally based three dimensional networks

  摘要：

  Fourfold Heck reaction on tetraphenylmethane provides a promising 'one-step' synthetic methodology for construction of centrally based three dimensional aromatic networks. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10764-x

文献信息

• Synthesis, Spectroscopy, and Morphology of Tetrastilbenoidmethanes
  作者：Warren J. Oldham、Rene J. Lachicotte、Guillermo C. Bazan

  DOI：10.1021/ja974209x

  日期：1998.4.1

  materials are currently being considered for the active component in a variety of optoelectronic devices, most notably as the emissive layer in light-emitting diodes. 1 It is generally believed that the morphology adopted by these materials plays a fundamental role in defining their bulk performance. For example, completely amorphous and ultrapure thin films appear to provide the longest device lifetimes,

  目前正在考虑将低带隙分子和聚合物有机材料用作各种光电器件中的活性组件，最显着的是作为发光二极管中的发射层。1 人们普遍认为，这些材料采用的形态在定义它们的整体性能方面起着重要作用。例如，完全非晶态和超纯薄膜似乎可以提供最长的器件寿命，同时具有最高的效率和发光亮度。2 虽然通过在高真空下升华可以获得足够纯的低分子量荧光化合物薄膜，但这些薄膜会随着时间的推移而重结晶，从而导致设备故障。3 发光聚合物材料可以设计成保持无定形，即使在高温下，但它们更难获得高纯度。4,5 此外，固态聚合物链的紧密结合会导致结晶域。6 有序聚合物区域似乎通过促进低能量非或弱发射准分子或聚集态来降低发射效率。7 最终，由于容易的能量迁移，这些低能量位点可以主导光学特性，即使存在的浓度很小。8 即使以很小的浓度存在。8 即使以很小的浓度存在。8
• Synthesis, Morphology, and Optical Properties of Tetrahedral Oligo(phenylenevinylene) Materials
  作者：Shujun Wang、Warren J. Oldham、Raymond A. Hudack,、Guillermo C. Bazan

  DOI：10.1021/ja992924w

  日期：2000.6.1

  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.