tribromo(1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl)silane | 1187583-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: tribromo(1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl)silane
• 英文别名: Tribromo-(1,1,3,3,5,5,7,7-octaethyl-2,6-dihydro-s-indacen-4-yl)silane；tribromo-(1,1,3,3,5,5,7,7-octaethyl-2,6-dihydro-s-indacen-4-yl)silane
• CAS: 1187583-43-2
• 化学式: C₂₈H₄₅Br₃Si
• 分子量: 649.463
• InChiKey: SNPZGABEMQIMGD-UHFFFAOYSA-N

物化性质

• 沸点：
  525.9±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.06
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  tribromo(1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl)silane 在 正丁基锂 、 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (E)-(1,1,3,3,5,5,7,7-octaethyl-2,6-dihydro-s-indacen-4-yl)-[(1,1,3,3,5,5,7,7-octaethyl-2,6-dihydro-s-indacen-4-yl)-thiophen-2-ylsilylidene]-thiophen-2-ylsilane
  参考文献：
  名称：

  Si═Si双键与噻吩环之间的π共轭：1,2-双（噻吩-2-基）二ilene和1,2-双（2,2'-联噻吩-）的合成，结构特征和光物理性质5-基）二ilene

  摘要：

  两种新的二ilene化合物，1,2-双（噻吩-2-基）disilene（1）和1,2-双（2,2'-bithiophen-5-yl）二ilene（2），由稠合的-环笨重EIND基（EIND = -1,1,3,3,5,5,7,7- octaethyl-小号-hydrindacen -4-基）已经分别获得橙色和紫色晶体，由相应的减小二溴硅烷。它们的X射线结构和光谱性质证明了Si═Si双键和噻吩单元之间有效的π共轭。值得注意的是，基于基本共面的1，2-双（噻吩基）二ilene骨架，在室温下，在溶液中和在固态下，π-扩展的2均显示出不同的发射。的结构特征和电子性质1和2已在实验和计算上进行了彻底表征。

  DOI：

  10.1021/acs.organomet.7b00370
• 作为产物：
  描述：

  4-溴-1,1,3,3,5,5,7,7-八乙基-1,2,3,5,6,7-六氢对称引达省 在 正丁基锂 、 四溴化碳 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 121.0h， 生成 tribromo(1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl)silane
  参考文献：
  名称：

  Room-Temperature Dissociation of 1,2-Dibromodisilenes to Bromosilylenes

  摘要：

  A room-temperature dynamic equilibrium between dibromodisilenes and bromosilylenes has been demonstrated by taking advantage of the steric protection using the fused-ring bulky 1,1,3,3,5,5,7,7-octa-R-s-hydrindacen-4-yl (Rind) groups. Although the bromosilylenes cannot be directly observed by spectroscopic methods, the thermal homolytic cleavage of the Si=Si double bond has been confirmed by a pseudo-first-order kinetics for the trapping with bis(trimethylsilyl)acetylene and a crossover reaction using two kinds of Rind-substituted dibromodisilenes. The addition of 4-pyrrolidinopyridine (PPy) to the dibromodisilene leads to an equilibrium mixture between the dibromodisilene and a PPy adduct of bromosilylene, the latter being isolated and characterized. The substitution of the bromine atom in the dibromodisilene by the Grignard reagent is significantly accelerated by the addition of PPy.

  DOI：

  10.1021/ja209736d

文献信息

• (<i>Z</i>)-1,2-Di(1-pyrenyl)disilene: Synthesis, Structure, and Intramolecular Charge-Transfer Emission
  作者：Megumi Kobayashi、Naoki Hayakawa、Tsukasa Matsuo、Baolin Li、Takeo Fukunaga、Daisuke Hashizume、Hiroyuki Fueno、Kazuyoshi Tanaka、Kohei Tamao

  DOI：10.1021/jacs.5b11970

  日期：2016.1.27

  (Z)-1,2-Di(1-pyrenyl)disilene containing bulky 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl (Eind) groups has been obtained as purple crystals by the reductive coupling reaction of the corresponding dibromosilane with lithium naphthalenide. An X-ray crystallographic analysis revealed an Eind- and pyrenyl-meshed molecular gear around the disilene core adopting the Z configuration, in which the two pyrenyl

  (Z)-1,2-Di(1-pyrenyl)disilene 含有庞大的 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl (Eind) 基团已获得如下通过相应的二溴硅烷与萘化锂的还原偶联反应生成紫色晶体。X 射线晶体学分析显示，在采用 Z 构型的二硅烯核周围有 Eind 和芘基啮合的分子齿轮，其中两个芘基通过 π-π 堆积在分子内相互作用，中心之间的距离为 3.635 Å。两个芘环。二硅烷 π 系统在室温下表现出 π(Si-Si) → π*(芘) 分子内电荷转移 (ICT) 荧光，其波长取决于溶剂极性。包括激发态计算在内的计算研究在理论上支持光物理特性。
• π-Conjugated Phosphasilenes Stabilized by Fused-Ring Bulky Groups
  作者：Baolin Li、Tsukasa Matsuo、Daisuke Hashizume、Hiroyuki Fueno、Kazuyoshi Tanaka、Kohei Tamao

  DOI：10.1021/ja9051153

  日期：2009.9.23

  pi-Conjugated phosphasilenes with a variety of aryl substituents on the silicon atom have been synthesized by the use of a 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl (Eind) group. X-ray structural analysis shows the highly coplanar pi-framework stabilized by the perpendicularly fixed Eind groups. The strong pi-pi* absorptions have been observed, demonstrating the extension of pi-conjugation over the skeleton. The DFT calculations indicate that the LUMO involves the substantial contribution of the 3p pi*(Si- P)-2p(pi)*(carbon pi-electron system) conjugation. The electrochemical properties of the phosphasilens are also presented.
• π-Conjugation between a Si═Si Double Bond and Thiophene Rings: Synthesis, Structural Characteristics, and Photophysical Properties of 1,2-Bis(thiophen-2-yl)disilene and 1,2-Bis(2,2′-bithiophen-5-yl)disilene
  作者：Naoki Hayakawa、Shogo Nishimura、Nobuhiro Kazusa、Nozomu Shintani、Tsukasa Nakahodo、Hisashi Fujihara、Manabu Hoshino、Daisuke Hashizume、Tsukasa Matsuo

  DOI：10.1021/acs.organomet.7b00370

  日期：2017.9.11

  new disilene compounds, 1,2-bis(thiophen-2-yl)disilene (1) and 1,2-bis(2,2′-bithiophen-5-yl)disilene (2), supported by the fused-ring bulky Eind groups (Eind = 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl) have been obtained as orange and purple crystals, respectively, by the reduction of the corresponding dibromosilanes. Their X-ray structures and spectroscopic properties demonstrate the effective

  两种新的二ilene化合物，1,2-双（噻吩-2-基）disilene（1）和1,2-双（2,2'-bithiophen-5-yl）二ilene（2），由稠合的-环笨重EIND基（EIND = -1,1,3,3,5,5,7,7- octaethyl-小号-hydrindacen -4-基）已经分别获得橙色和紫色晶体，由相应的减小二溴硅烷。它们的X射线结构和光谱性质证明了Si═Si双键和噻吩单元之间有效的π共轭。值得注意的是，基于基本共面的1，2-双（噻吩基）二ilene骨架，在室温下，在溶液中和在固态下，π-扩展的2均显示出不同的发射。的结构特征和电子性质1和2已在实验和计算上进行了彻底表征。
• Room-Temperature Dissociation of 1,2-Dibromodisilenes to Bromosilylenes
  作者：Katsunori Suzuki、Tsukasa Matsuo、Daisuke Hashizume、Kohei Tamao

  DOI：10.1021/ja209736d

  日期：2011.12.14

  A room-temperature dynamic equilibrium between dibromodisilenes and bromosilylenes has been demonstrated by taking advantage of the steric protection using the fused-ring bulky 1,1,3,3,5,5,7,7-octa-R-s-hydrindacen-4-yl (Rind) groups. Although the bromosilylenes cannot be directly observed by spectroscopic methods, the thermal homolytic cleavage of the Si=Si double bond has been confirmed by a pseudo-first-order kinetics for the trapping with bis(trimethylsilyl)acetylene and a crossover reaction using two kinds of Rind-substituted dibromodisilenes. The addition of 4-pyrrolidinopyridine (PPy) to the dibromodisilene leads to an equilibrium mixture between the dibromodisilene and a PPy adduct of bromosilylene, the latter being isolated and characterized. The substitution of the bromine atom in the dibromodisilene by the Grignard reagent is significantly accelerated by the addition of PPy.