1,1-dimethyl-2-phenyl-3-trimethylstannylbenzo[b]silole | 1016642-72-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,1-dimethyl-2-phenyl-3-trimethylstannylbenzo[b]silole
• 英文别名: (1,1-Dimethyl-2-phenyl-1-benzosilol-3-yl)-trimethylstannane
• CAS: 1016642-72-0
• 化学式: C₁₉H₂₄SiSn
• 分子量: 399.195
• InChiKey: BTHDUSMIUPXADB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1,1-dimethyl-2-phenyl-3-trimethylstannylbenzo[b]silole 在 碘 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到1,1-dimethyl-3-iodo-2-phenylbenzo[b]silole
  参考文献：
  名称：

  Modular Synthesis of Functionalized Benzosiloles by Tin-Mediated Cyclization of (o-Alkynylphenyl)silane

  摘要：

  Trimethylstannyllithium promotes cyclization of (o-alkynylphenyl) silane into a 3-stannylbenzosilole, via addition to the triple bond followed by intramolecular cyclization in a cascade fashion. This intermediate can be functionalized with either electrophiles or nucleophiles to allow modular synthesis of 2,3-disubstituted benzosiloles. One of these compounds, a phenylene-bis (benzosilole) compound, shows electron drift mobility as high as 6 x 10(-4) cm(2/)Vs in an amorphous film, making this class of compounds promising electronic materials for organic light emitting devices and organic photovoltaic cells.

  DOI：

  10.1021/ja800636g
• 作为产物：
  描述：

  (trimethylstannyl)lithium 、 dimethyl(2-(phenylethynyl)phenyl)silane 在 diethyl ether or tetramethylethylenediamine 作用下， 以 正己烷 为溶剂， 以90%的产率得到1,1-dimethyl-2-phenyl-3-trimethylstannylbenzo[b]silole
  参考文献：
  名称：

  Modular Synthesis of Functionalized Benzosiloles by Tin-Mediated Cyclization of (o-Alkynylphenyl)silane

  摘要：

  Trimethylstannyllithium promotes cyclization of (o-alkynylphenyl) silane into a 3-stannylbenzosilole, via addition to the triple bond followed by intramolecular cyclization in a cascade fashion. This intermediate can be functionalized with either electrophiles or nucleophiles to allow modular synthesis of 2,3-disubstituted benzosiloles. One of these compounds, a phenylene-bis (benzosilole) compound, shows electron drift mobility as high as 6 x 10(-4) cm(2/)Vs in an amorphous film, making this class of compounds promising electronic materials for organic light emitting devices and organic photovoltaic cells.

  DOI：

  10.1021/ja800636g

文献信息

• Modular Synthesis of Polybenzo[<i>b</i>]silole Compounds for Hole-Blocking Material in Phosphorescent Organic Light Emitting Diodes
  作者：Laurean Ilies、Yoshiharu Sato、Chikahiko Mitsui、Hayato Tsuji、Eiichi Nakamura

  DOI：10.1002/asia.201000112

  日期：——

  utilized as efficient hole‐blocking materials for phosphorescent organic light emitting diodes (OLEDs). Some of these compounds showed a performance surpassing that of the current standard, bathocuproine. The new compounds were easily synthesized in a modular fashion from a previously reported 3‐stannyl benzosilole building unit. Studies on the properties of these compounds in solution and in the solid state

  面向多样性的合成策略使我们能够设计一系列包含多个苯并甲硅烷基单元的共轭分子，这些共轭分子可用作磷光有机发光二极管（OLED）的有效空穴阻挡材料。这些化合物中的一些表现出超过当前标准浴铜嘌呤的性能。新化合物很容易以模块化方式由先前报道的3-锡烷基苯并甲硅烷基建筑单元合成。对这些化合物在溶液和固态下的性质的研究表明，它们具有高电子亲和力，高电离势能，并形成显示出高电子漂移迁移率的稳定非晶膜。还研究了它们的分子性质与OLED器件性能效率之间的相关性。
• Modular Synthesis of Functionalized Benzosiloles by Tin-Mediated Cyclization of (<i>o</i>-Alkynylphenyl)silane
  作者：Laurean Ilies、Hayato Tsuji、Yoshiharu Sato、Eiichi Nakamura

  DOI：10.1021/ja800636g

  日期：2008.4.1

  Trimethylstannyllithium promotes cyclization of (o-alkynylphenyl) silane into a 3-stannylbenzosilole, via addition to the triple bond followed by intramolecular cyclization in a cascade fashion. This intermediate can be functionalized with either electrophiles or nucleophiles to allow modular synthesis of 2,3-disubstituted benzosiloles. One of these compounds, a phenylene-bis (benzosilole) compound, shows electron drift mobility as high as 6 x 10(-4) cm(2/)Vs in an amorphous film, making this class of compounds promising electronic materials for organic light emitting devices and organic photovoltaic cells.