1-(3',5'-di-4'-tert-butylstyryl)-4-(4'-vinylstyryl)benzene | 372076-61-4

• 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: 1-(3',5'-di-4'-tert-butylstyryl)-4-(4'-vinylstyryl)benzene
• 英文别名: 1-(3'5'-Di-tert-butylstyryl)-4-(4'-vinylstyryl)benzene；1,3-ditert-butyl-5-[2-[4-[2-(4-ethenylphenyl)ethenyl]phenyl]ethenyl]benzene
• CAS: 372076-61-4
• 化学式: C₃₂H₃₆
• 分子量: 420.638
• InChiKey: UHIIWUMZPFNTJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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-碘-4-[三(4-碘苯基)甲基]苯 、 1-(3',5'-di-4'-tert-butylstyryl)-4-(4'-vinylstyryl)benzene 在 palladium diacetate 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 63.5h， 以74%的产率得到tetrakis(4-(4'-(3'',5''-di-tert-butylstyryl)styryl)stilbenyl)methane
  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：

  4-vinylbenzyltriphenylphosphonium chloride 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 46.0h， 生成 1-(3',5'-di-4'-tert-butylstyryl)-4-(4'-vinylstyryl)benzene
  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

• Soluble tetrahedral compounds for use in electroluminescent devices
  申请人：The Regents of the University of California

  公开号：US06824890B2

  公开（公告）日：2004-11-30

  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.

  本发明涉及电致发光化合物、器件及其制备方法，采用一种新颖的拓扑策略设计适用于形成光电器件中薄膜的非晶态分子固体。在该方法中，色团被连接到四面体汇合点。
• 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.