1,4-bis(1,1,3-trimethyl-1H-1-silainden-2-yl)benzene

• 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: 1,4-bis(1,1,3-trimethyl-1H-1-silainden-2-yl)benzene
• 英文别名: 1,1,3-trimethyl-2-[4-(1,1,3-trimethyl-1-benzosilol-2-yl)phenyl]-1-benzosilole
• 化学式: C₂₈H₃₀Si₂
• 分子量: 422.717
• InChiKey: XXQNYXBXKOGCIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 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(1,1,3-trimethyl-1H-1-silainden-2-yl)benzene 、 锂 、 萘 、 、 硫酸二甲酯 以 四氢呋喃 为溶剂， 反应 8.08h， 生成
  参考文献：
  名称：

  Polycyclic fused ring type π-conjugated organic material, intermediate therefor, process for producing polycyclic fused ring type π-conjugated organic material, and process for producing intermediate of polycyclic fused ring type π-conjugated organic material

  摘要：

  通过以下方法获得多环融合环式π-共轭有机材料(VIIa、VIIb、VIIc、VIId)。如下图1所示，起始材料(I)通过有机金属碱二金属化。因此，二金属化的起始材料(I)被有机硅试剂(i: (1) n-BuLi或t-BuLi; (2) HMe2SiCl)捕获，从而得到中间体。然后，中间体与金属还原剂反应，引起分子内还原环化反应。结果，产生一个二阴离子中间体。该二阴离子中间体与电子亲和体(ii: (1) LiNaph、THF、rt、5分钟; (2) 电子亲和体或NH4Cl)结合，从而得到多环融合环式π-共轭有机材料。通过该方法，可以提供具有优异发光和载流性能的多环融合环式π-共轭有机材料，以及其中间体的制备方法和多环融合环式π-共轭有机材料的制备方法。

  公开号：

  US07973190B2
• 作为产物：
  描述：

  二甲基硫 在 萘 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 8.08h， 以83%的产率得到1,4-bis(1,1,3-trimethyl-1H-1-silainden-2-yl)benzene
  参考文献：
  名称：

  POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIALS, INTERMEDIATE THEREFOR, PROCESS FOR PRODUCING POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIALS, AND PROCESS FOR PRODUCING INTERMEDIATE FOR POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIALS

  摘要：

  公开号：

  EP1700860B1

文献信息

• Synthesis, structures, and photophysical properties of silicon and carbon-bridged ladder oligo(p-phenylenevinylene)s and related π-electron systems
  作者：Shigehiro Yamaguchi、Caihong Xu、Hiroshi Yamada、Atsushi Wakamiya

  DOI：10.1016/j.jorganchem.2005.05.019

  日期：2005.11

  partially or fully fused ladder oligo(p-phenylenevinylene)s (LOPVs) and related π-electron systems has been synthesized. Thus, the intramolecular reductive cyclization of o-silyl-substituted bis(phenylethynyl)benzenes with lithium naphthalenide produces partially silicon-bridged bis(styryl)benzenes consisting of silaindene or disilaindacene skeletons. By combining this cyclization with the Friedel–Crafts type

  合成了一系列部分或完全稠合的梯形低聚对苯撑亚乙烯基（LOPVs）和相关的π电子体系。因此，o的分子内还原环化带有萘二甲酸锂的-甲硅烷基取代的双（苯乙炔基）苯可生产部分由硅杂茚或双硅二并丁烯骨架组成的硅桥联双（苯乙烯基）苯。通过将此环化与Friedel-Crafts型亲电环化相结合，已经以相当高的产率合成了一系列完全融合的，带有硅和碳桥的LOPV和相关化合物的同源物。LOPV的最长示例是13环稠合系统，其具有近乎平坦的π共轭骨架，长度为2.9 nm，这已通过X射线晶体学证明。所有产生的梯形π电子系统在可见光区域都显示出强烈的荧光，具有高量子产率以及相对较小的斯托克斯位移。随着硅含量的增加或掺入二硅双并丁烯骨架，发射最大值移至更长的波长，荧光量子产率略有下降。这些趋势可以归因于硅的σ*效应，其中硅桥通过σ*-π*的轨道相互作用对电子结构有贡献，这些相互作用引起发射最大值的红移并抑制来自电子发射的辐射衰减过程。单重态激发态。
• General Silaindene Synthesis Based on Intramolecular Reductive Cyclization toward New Fluorescent Silicon-Containing π-Electron Materials
  作者：Caihong Xu、Atsushi Wakamiya、Shigehiro Yamaguchi

  DOI：10.1021/ol0486932

  日期：2004.10.1

  [reaction: see text] The reaction of (o-silylphenyl)acetylene derivatives with lithium naphthalenide undergoes intramolecular reductive cyclization to produce various silaindene derivatives. On the basis of this methodology, a series of silaindene-containing pi-electron systems are synthesized that show intense blue to greenish-blue fluorescence.

  [反应：见正文]（邻甲硅烷基苯基）乙炔衍生物与萘锂的反应进行分子内还原环化反应，制得各种硅茚衍生物。在此方法的基础上，合成了一系列含硅亚茚的π电子系统，这些系统显示出强烈的蓝色至绿色-蓝色荧光。
• POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIAL, INTERMEDIATE THEREFOR, PROCESS FOR PRODUCING POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIAL, AND PROCESS FOR PRODUCING INTERMEDIATE OF POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIAL
  申请人：Yamaguchi Shigehiro

  公开号：US20090143605A1

  公开（公告）日：2009-06-04

  A polycyclic fused ring type π-conjugated organic material (VIIa, VIIb, VIIc, VIId) is obtained in the following manner. That is, as shown in Scheme 1 below, a starting material (I) is dimetalated with an organometallic base. The starting material (I) thus dimetalated is trapped with an organosilicon reagent (i: (1) n-BuLi or t-BuLi; (2) HMe 2 SiCl). As a result, an intermediate is obtained. Thereafter, the intermediate is allowed to react with a metal reductant. This causes an intramolecular reductive cyclization reaction to proceed. As a result, a dianion intermediate is produced. The dianion intermediate is trapped with an electrophile (ii: (1) LiNaph, THF, rt, 5 min; (2) electrophile or NH 4 Cl) In this way, the polycyclic fused ring type π-conjugated organic material is obtained. The polycyclic fused ring type π-conjugated organic material, an intermediate therefor, a method for producing the polycyclic fused ring type π-conjugated organic material, and a method for producing the intermediate make it possible to provide a polycyclic fused ring type π-conjugated organic material having excellent light-emitting and charge-transporting properties.

  以下是用以下方法得到的多环融合环式π-共轭有机材料（VIIa、VIIb、VIIc、VIId）。即，如下所示的方案1，起始物质（I）与有机金属碱进行二金属化。因此，这样二金属化的起始物质（I）被有机硅试剂（i：（1）n-BuLi或t-BuLi；（2）HMe2SiCl）捕获。因此，得到了一个中间体。然后，中间体被允许与金属还原剂反应。这会导致分子内还原环化反应进行。因此，产生了一个二阴离子中间体。该二阴离子中间体被电子亲和体（ii：（1）LiNaph、THF、rt、5 min；（2）电子亲和体或NH4Cl）捕获。通过这种方式，可以获得多环融合环式π-共轭有机材料。该多环融合环式π-共轭有机材料及其中间体、制备多环融合环式π-共轭有机材料的方法以及制备中间体的方法使得可以提供具有优异发光和载流特性的多环融合环式π-共轭有机材料。
• POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIALS, INTERMEDIATE THEREFOR, PROCESS FOR PRODUCING POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIALS, AND PROCESS FOR PRODUCING INTERMEDIATE FOR POLYCYCLIC FUSED RING TYPE PI-CONJUGATED ORGANIC MATERIALS
  申请人：Japan Science and Technology Agency

  公开号：EP1700860B1

  公开（公告）日：2011-07-27
• Polycyclic fused ring type π-conjugated organic material, intermediate therefor, process for producing polycyclic fused ring type π-conjugated organic material, and process for producing intermediate of polycyclic fused ring type π-conjugated organic material
  申请人：Japan Science and Technology Agency

  公开号：US07973190B2

  公开（公告）日：2011-07-05

  A polycyclic fused ring type π-conjugated organic material (VIIa, VIIb, VIIc, VIId) is obtained in the following manner. That is, as shown in Scheme 1 below, a starting material (I) is dimetalated with an organometallic base. The starting material (I) thus dimetalated is trapped with an organosilicon reagent (i: (1) n-BuLi or t-BuLi; (2) HMe2SiCl). As a result, an intermediate is obtained. Thereafter, the intermediate is allowed to react with a metal reductant. This causes an intramolecular reductive cyclization reaction to proceed. As a result, a dianion intermediate is produced. The dianion intermediate is trapped with an electrophile (ii: (1) LiNaph, THF, rt, 5 min; (2) electrophile or NH4Cl) In this way, the polycyclic fused ring type π-conjugated organic material is obtained. The polycyclic fused ring type π-conjugated organic material, an intermediate therefor, a method for producing the polycyclic fused ring type π-conjugated organic material, and a method for producing the intermediate make it possible to provide a polycyclic fused ring type π-conjugated organic material having excellent light-emitting and charge-transporting properties.

  通过以下方法获得多环融合环式π-共轭有机材料(VIIa、VIIb、VIIc、VIId)。如下图1所示，起始材料(I)通过有机金属碱二金属化。因此，二金属化的起始材料(I)被有机硅试剂(i: (1) n-BuLi或t-BuLi; (2) HMe2SiCl)捕获，从而得到中间体。然后，中间体与金属还原剂反应，引起分子内还原环化反应。结果，产生一个二阴离子中间体。该二阴离子中间体与电子亲和体(ii: (1) LiNaph、THF、rt、5分钟; (2) 电子亲和体或NH4Cl)结合，从而得到多环融合环式π-共轭有机材料。通过该方法，可以提供具有优异发光和载流性能的多环融合环式π-共轭有机材料，以及其中间体的制备方法和多环融合环式π-共轭有机材料的制备方法。