1,4-bis(dimethylsilylvinyl)benzene | 202933-69-5

• 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: 1,4-bis(dimethylsilylvinyl)benzene
• 英文别名: [(E)-2-[4-[(E)-2-dimethylsilylethenyl]phenyl]ethenyl]-dimethylsilane
• CAS: 202933-69-5
• 化学式: C₁₄H₂₂Si₂
• 分子量: 246.5
• InChiKey: CBQQHYYIEFMXDB-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1,4-bis(dimethylsilylvinyl)benzene 在 Wilkinson's catalyst 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 1,4-bis{2-{2-[4'-[2-(β-styryldimethylsilyl)vinyl]biphenyl-4-yl]vinyl}dimethylsilylvinyl}benzene
  参考文献：
  名称：

  区域规则的甲硅烷基间隔的二芳烃共聚物的三发色团能量梯度合成及有效的能量转移

  摘要：

  通过铑催化双乙烯基硅烷3和双炔烃4的氢化硅烷化反应，可以得到由具有三种不同发色团的能量梯度的区域规则的甲硅烷基间隔的共聚物1。准备用于比较的单体参考化合物2。三个生色团的比例为1：2：1，分别对应于D 1，D 2和A生色团。二甲基甲硅烷基（SiMe 2）部分用作发色团之间的绝缘桥。激发供体生色团（D 1），仅观察到来自受体（A）的发射。在这些甲硅烷基间隔的共聚物中，沿着聚合物主链跨三个不同生色团的有效且连续的能量转移可能会顺利进行。

  DOI：

  10.1021/ma050140z
• 作为产物：
  描述：

  2,2'-p-phenylene-bis-[1,3]dithiolane 在 bis(triphenylphosphine)nickel(II) chloride 、 lithium aluminium tetrahydride 作用下， 以 苯 为溶剂， 反应 34.0h， 生成 1,4-bis(dimethylsilylvinyl)benzene
  参考文献：
  名称：

  A general synthesis of vinylic silyl hydrides using nickel catalysis. Applications to the syntheses of silylene-tethered conjugated polymers

  摘要：

  Treatment of benzylic or allylic dithioacetals with Me-2((PrO)-Pr-i)SiCH2MgCl in the presence of NiCl2(PPh3)(2) catalyst yielded the corresponding i-propoxy(vinyl)silanes which are reduced with LIAlH4, to afford vinylic silyl hydrides. These hydrides serve as the precursors for the syntheses of silylene-tethered sigma,pi-conjugated copolymers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10218-6

文献信息

• New Arylene–Germylene–Vinylene Compounds: Stereoselective Synthesis, Characterization, and Photophysical Properties
  作者：Monika Ludwiczak、Małgorzata Bayda、Michał Dutkiewicz、Dawid Frąckowiak、Mariusz Majchrzak、Bronisław Marciniak、Bogdan Marciniec

  DOI：10.1021/acs.organomet.6b00336

  日期：2016.8.8

  The stereoselective route toward new molecular and macromolecular compounds containing arylene-germylene-vinylene units is described. The reagents for germylative coupling reaction were 1,4-bis(dimethylvinylgermyl)benzene (1) and vinyl-and divinylarenes with ruthenium complexes (2a, 2b) as catalysts. NMR characterization of all isolated products, results of MS and elemental analysis for molecular compounds (3-5), and GPC for oligomers (6-8) are presented. Absorption and luminescence properties of the synthesized compounds are discussed and compared with those of model chromophores.
• Synthesis and Photophysical Studies of Silylene-Spaced Divinylarene Copolymers. Molecular Weight Dependent Fluorescence of Alternating Silylene−Divinylbenzene Copolymers
  作者：Ruey-Min Chen、Kuo-Ming Chien、Ken-Tsung Wong、Bih-Yaw Jin、Tien-Yau Luh、Jui-Hung Hsu、Wunshain Fann

  DOI：10.1021/ja971373b

  日期：1997.11.1
• Norbornadiene as an Efficient Hydrogen Scavenger for the Palladium-Catalyzed Conversion of Hydrosilanes to Alkoxysilanes
  作者：Sundarraj Sudhakar、Tien-Yau Luh

  DOI：10.1021/jo025886z

  日期：2002.9.1

  A palladium-catalyzed mild and efficient method for the alcoholysis of hydrosilanes containing a C=C bond in the presence of norbornadiene (NBD) is reported. The highly strained NBD acts as a hydrogen scavenger, which abstracts the hydrogen produced during the process, protecting the C=C bond from being hydrogenated.
• A general synthesis of vinylic silyl hydrides using nickel catalysis. Applications to the syntheses of silylene-tethered conjugated polymers
  作者：Ruey-Min Chen、Tien-Yau Luh

  DOI：10.1016/s0040-4020(97)10218-6

  日期：1998.2

  Treatment of benzylic or allylic dithioacetals with Me-2((PrO)-Pr-i)SiCH2MgCl in the presence of NiCl2(PPh3)(2) catalyst yielded the corresponding i-propoxy(vinyl)silanes which are reduced with LIAlH4, to afford vinylic silyl hydrides. These hydrides serve as the precursors for the syntheses of silylene-tethered sigma,pi-conjugated copolymers. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and Efficient Energy Transfer in a Three-Chromophore Energy Gradient of Regioregular Silylene-Spaced Divinylarene Copolymers
  作者：Yen-Ju Cheng、Tien-Yau Luh

  DOI：10.1021/ma050140z

  日期：2005.5.1

  Regioregular silylene-spaced copolymers 1 composed of an energy gradient with three different chromophores have been achieved by rhodium-catalyzed hydrosilylation of bis-vinylsilanes 3 and bis-alkynes 4. Monomeric reference compounds 2 were prepared for comparison. The ratio of three chromophores is 1:2:1, corresponding to D1, D2, and A chromophores, respectively. The dimethylsilylene (SiMe2) moiety

  通过铑催化双乙烯基硅烷3和双炔烃4的氢化硅烷化反应，可以得到由具有三种不同发色团的能量梯度的区域规则的甲硅烷基间隔的共聚物1。准备用于比较的单体参考化合物2。三个生色团的比例为1：2：1，分别对应于D 1，D 2和A生色团。二甲基甲硅烷基（SiMe 2）部分用作发色团之间的绝缘桥。激发供体生色团（D 1），仅观察到来自受体（A）的发射。在这些甲硅烷基间隔的共聚物中，沿着聚合物主链跨三个不同生色团的有效且连续的能量转移可能会顺利进行。