1-(pentamethyldisilyl)naphthalene | 38446-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(pentamethyldisilyl)naphthalene
• 英文别名: 1-pentamethyldisilanylnaphthalene；1-pentamethyl-disilylnaphthalene；1-naphthylpentamethyldisilane；1-Pentamethyldisilanyl-naphthalin；Disilane, pentamethyl-1-naphthalenyl-；dimethyl-naphthalen-1-yl-trimethylsilylsilane
• CAS: 38446-40-1
• 化学式: C₁₅H₂₂Si₂
• 分子量: 258.511
• InChiKey: HOCAJYZQOFSYAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  306.1±11.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-(pentamethyldisilyl)naphthalene 生成 1-Dimethylsilanyl-2-trimethylsilanyl-naphthalene
  参考文献：
  名称：

  苯基硅烷和萘基硅烷的光化学和光物理行为

  摘要：

  苯基和萘基硅烷的光化学和光物理性质已被定量研究。据发现，naphthyldisilanes的光化学反应从分子内电荷转移状态起源1（2 Pπ，3 dπ由2生产）Pπ * →3 dπ电荷转移。重排（ϕ r）和减少（ϕ R）在254 nm处的量子产率和量子产率（ϕ ct），由于溶剂间的快速系统交叉（通过电荷转移状态）与辐射速率和反应速率竞争，二硅烷基萘的电荷转移发射显着降低。已经获得了光化学反应的活化参数。已经证明，将二硅烷基基团取代成苯基或萘基基团不仅强烈影响光化学反应，而且强烈影响包含快速系统间穿越的光物理过程。

  DOI：

  10.1039/f19848000383
• 作为产物：
  描述：

  一氯五甲基二硅烷 、 1-溴代萘 在 正丁基锂 作用下， 以 正己烷 为溶剂， 生成 1-(pentamethyldisilyl)naphthalene
  参考文献：
  名称：

  π−π and σ−π Interactions in α,ω-Di-(9-anthryl) and Di-(1-naphthyl) Oligosilanes Studied by Time-Resolved Fluorescence in Solution

  摘要：

  The photophysical properties of two series of oligosilanes, (1-naphthyl)-(SiMe2)(n)-(1-naphthyl) (1-5) and (9-anthryl)-(SiMe2)(n)-(9-anthryl) (6-10) with n = 1-4 and 6, were investigated. In these compounds, two types of interactions, a pi-pi interaction between two aromatic groups and a sigma-pi interaction between aromatics and: a silicon chain unit, were observed. Intramolecular excimer emission was observed in cyclohexane when n greater than or equal to 2. The strongest excimer emission of 2 and 7 is different from the Hirayama rule (n = 3) proposed for carbon analogues and also shows that intramolecular cycloaddition is minor. The time-resolved fluorescence speptra of an anthryl series revealed that the time constant of excimer formation varied depending on the chain length (82-152 ps). In the cases of 4, 5, and 10, charge-transfer (CT) emission was observed in acetonitrile or THF. The time constant of the CT-state formation for 10 was relatively slow (45 ps), which may indicate a conformational change. Monomer emission from the locally excited state was observed for I and 6 in both cyclohexane and acetonitrile.

  DOI：

  10.1021/jp0355760

文献信息

• Photochemical carbon-silicon bond forming reaction on electron-deficient alkenes by disilanes and polysilanes via photoinduced electron transfer
  作者：Kazuhiko Mizuno、Kazuhisa Nakanishi、Jun-ichi Chosa、Yoshio Otsuji

  DOI：10.1016/0022-328x(94)80103-7

  日期：1994.6

  of electron-deficient alkenes with disilanes in acetonitrile gave silylated alkanes in high yields. The photosilylation occurred in a highly regioselective manner at the position β to the electron-withdrawing groups of the alkenes. With asymmetrically substituted disilanes and polysilanes, silyl groups bearing more bulky substituents were preferentially introduced to the alkenes. The photoreactions were

  缺电子的烯烃与乙硅烷在乙腈中的菲敏光反应可得到高产率的甲硅烷基化的烷烃。在烯的吸电子基团的位置β处以高度区域选择性的方式发生光硅烷化。对于不对称取代的乙硅烷和聚硅烷，优选将带有更大体积取代基的甲硅烷基引入烯烃中。光反应被芳香烃（如菲和苯并菲）敏化，但不被pyr或蒽敏化。在没有芳族烃的情况下，光反应是不明显的。光反应的关键步骤是与甲硅烷基自由基的缺电子烯烃与自由基阴离子的反应，它们是由乙硅烷和聚硅烷的自由基阳离子的亲核试剂裂解产生的。讨论了光反应的机理。
• Photochemical and photophysical behaviour of phenylsilanes and naphthylsilanes
  作者：Haruo Shizuka、Hidesumi Obuchi、Mitsuo Ishikawa、Makoto Kumada

  DOI：10.1039/f19848000383

  日期：——

  naphthyldisilanes originates from the intramolecular charge-transfer state 1(2pπ, 3dπ) produced by 2pπ*→ 3dπ charge transfer. The rearrangement (ϕr) and decrease (ϕR) quantum yields at 254 nm and the quantum yield (ϕct) for the charge-transfer emission for disilanylnaphthalenes decreased markedly with solvent polarity because of fast intersystem crossing (through the charge-transfer state) in competition with

  苯基和萘基硅烷的光化学和光物理性质已被定量研究。据发现，naphthyldisilanes的光化学反应从分子内电荷转移状态起源1（2 Pπ，3 dπ由2生产）Pπ * →3 dπ电荷转移。重排（ϕ r）和减少（ϕ R）在254 nm处的量子产率和量子产率（ϕ ct），由于溶剂间的快速系统交叉（通过电荷转移状态）与辐射速率和反应速率竞争，二硅烷基萘的电荷转移发射显着降低。已经获得了光化学反应的活化参数。已经证明，将二硅烷基基团取代成苯基或萘基基团不仅强烈影响光化学反应，而且强烈影响包含快速系统间穿越的光物理过程。
• π−π and σ−π Interactions in α,ω-Di-(9-anthryl) and Di-(1-naphthyl) Oligosilanes Studied by Time-Resolved Fluorescence in Solution
  作者：Takashi Karatsu、Toshifumi Shibata、Atsuko Nishigaki、Akihide Kitamura、Yusuke Hatanaka、Yoshinobu Nishimura、Shin-ichiro Sato、Iwao Yamazaki

  DOI：10.1021/jp0355760

  日期：2003.11.1

  The photophysical properties of two series of oligosilanes, (1-naphthyl)-(SiMe2)(n)-(1-naphthyl) (1-5) and (9-anthryl)-(SiMe2)(n)-(9-anthryl) (6-10) with n = 1-4 and 6, were investigated. In these compounds, two types of interactions, a pi-pi interaction between two aromatic groups and a sigma-pi interaction between aromatics and: a silicon chain unit, were observed. Intramolecular excimer emission was observed in cyclohexane when n greater than or equal to 2. The strongest excimer emission of 2 and 7 is different from the Hirayama rule (n = 3) proposed for carbon analogues and also shows that intramolecular cycloaddition is minor. The time-resolved fluorescence speptra of an anthryl series revealed that the time constant of excimer formation varied depending on the chain length (82-152 ps). In the cases of 4, 5, and 10, charge-transfer (CT) emission was observed in acetonitrile or THF. The time constant of the CT-state formation for 10 was relatively slow (45 ps), which may indicate a conformational change. Monomer emission from the locally excited state was observed for I and 6 in both cyclohexane and acetonitrile.