(3,5-di-tert-butylbenzyl)triphenylphosphonium bromide | 36393-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3,5-di-tert-butylbenzyl)triphenylphosphonium bromide
• 英文别名: 3,5-di-4-tert-butylbenzyltriphenylphosphonium bromide；(3,5-Di-tert-butylbenzyl)triphenylphosphoniumbromid；3,5-di-tert-butylbenzyltriphenylphosphonium bromide；3,5-di-t-butylbenzyltriphenylphosphonium bromide；3,5-Di-tert-butylbenzylphosphoniumbromid；(3,5-Ditert-butylphenyl)methyl-triphenylphosphanium;bromide
• CAS: 36393-44-9
• 化学式: Br*C₃₃H₃₈P
• 分子量: 545.542
• InChiKey: AKAQZOPGYSSZIF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3,5-di-tert-butylbenzyl)triphenylphosphonium bromide 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：

  3,5-二叔丁基甲苯 在 溴 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 1.5h， 生成 (3,5-di-tert-butylbenzyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Risch, Nikolaus; Meyer-Roscher, Bernd; Langhals, Maria, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 1, p. 141 - 144

  摘要：

  DOI：

文献信息

• 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。
• Conformational studies on hexahelicenes—II
  作者：W.H. Laarhoven、R.G.M. Veldhuis

  DOI：10.1016/0040-4020(72)88060-8

  日期：1972.1

  The synthesis of eight alkyl substituted hexahelicene derivatives by photodehydrocyclization is described.

  描述了通过光脱氢环化反应合成八个烷基取代的六亚庚烯衍生物。
• Multiply charged anions from molecules with extended π-systems
  作者：Rainer Schenk、Klaus Müllen、Olof Wennerström

  DOI：10.1016/s0040-4039(00)88569-x

  日期：1990.1

  been prepared by alkali metal reduction of molecules built from benzene rings joined by vinylene groups. Thus, a tetra(stilbenyl)ethylene can be reduced to an octaanion and a [28]paracyclophaneoctaene to three different anions, assigned as the tetra-, hexa-, and octaanion, respectively. The hexaanion, a cyclic 54 π-electron system, is diatropic.

  通过碱金属还原由亚乙烯基连接的苯环构建的分子，可以制备带多个电荷的阴离子。因此，可以将四（二苯乙烯基）乙烯还原成八种阴离子，将[2 8 ]对环环辛八烯还原成三种不同的阴离子，分别指定为四，六和八阴离子。六价阴离子是环状的54π电子系统，具有变通性。
• On the effect of cyclodextrin on the Z/E-selectivity of Wittig Reactions with semistabilized ylides
  作者：Gunnar Westman、Olof Wennerström、Ilona Raston

  DOI：10.1016/s0040-4020(01)80315-x

  日期：1993.1

  The Z/E-selectivity of Wittig reactions between semistabilized ylids and aromatic aldehydes is affected by the addition of host molecules such as cyclodextrins (CD). An increase in the Z-selectivity from 57 to 92% has been reached with DMF as solvent and an increase in the E-selectivity from 67 to 80% has been reached with ethanol as solvent for the same Wittig reaction. Reactions with arenes with bulky

  半稳定分子和芳族醛之间Wittig反应的Z / E选择性受主体分子（例如环糊精（CD））的添加的影响。对于相同的Wittig反应，使用DMF作为溶剂，Z-选择性从57％增加到92％，并且使用乙醇作为溶剂，E-选择性从67％增加到80％。与芳烃具有大的取代基的反应可防止与环糊精络合的反应较少受到影响。我们将根据有关Wittig反应机理的最新结果对我们的结果进行讨论，并最好根据Vedejs四中心机理对其进行合理化。
• The charge storage mechanism of conducting polymers: a voltammetric study on defined soluble oligomers of the phenylene–vinylene type
  作者：Jürgen Heinze、John Mortensen、Klaus Müllen、Rainer Schenk

  DOI：10.1039/c39870000701

  日期：——

  The reductive charging–discharging behaviour of several newly synthesized soluble oligo-p-phenylene-vinylenes was studied by cyclic voltammetry; the results show that both the number of redox states and the magnitude of their energetic interaction depend on the chain length of the corresponding oligomer.

  通过循环伏安法研究了几种新合成的可溶性低聚对亚苯基亚乙烯基的还原性充放电行为。结果表明，氧化还原态的数量及其能量相互作用的大小均取决于相应的低聚物的链长。