2,2'-bithiophen-5-yl[bis(5'-hexyl-2,2'-bithiophen-5-yl)]methylsilane | 1036999-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2,2'-bithiophen-5-yl[bis(5'-hexyl-2,2'-bithiophen-5-yl)]methylsilane
• 英文别名: 2,2'-bithien-5-yl[bis(5'-hexyl-2,2'-bithien-5-yl)]methylsilane；Bis[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-methyl-(5-thiophen-2-ylthiophen-2-yl)silane
• CAS: 1036999-12-8
• 化学式: C₃₇H₄₂S₆Si
• 分子量: 707.222
• InChiKey: SKTZDUDHCHWAIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基三氯硅烷 、 2,2'-bithiophen-5-yl[bis(5'-hexyl-2,2'-bithiophen-5-yl)]methylsilane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以65%的产率得到Tris[5-[5-[bis[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-methylsilyl]thiophen-2-yl]thiophen-2-yl]-methylsilane
  参考文献：
  名称：

  Facile Synthesis and Optical Properties of Bithiophenesilane Monodendrons and Dendrimers

  摘要：

  Three generations of bithiophenesilane monodendrons and dendrimers consisting of 3-45 2,2'-bithiene-5,5'-diyl units were synthesized by means of effective coupling reactions between the corresponding bithienyllithium derivatives and chlorosilanes. These compounds show efficient photoluminescence in the violet-blue region, the quantum yield of which is 5-15 times higher than that for the parent bithiophene or bithiophenesilanes.

  DOI：

  10.1021/ol800811a
• 作为产物：
  描述：

  methyl(2,2'-bithien-5-yl)dichlorosilane 、 5-己基-2,2-二噻吩 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以90%的产率得到2,2'-bithiophen-5-yl[bis(5'-hexyl-2,2'-bithiophen-5-yl)]methylsilane
  参考文献：
  名称：

  Facile Synthesis and Optical Properties of Bithiophenesilane Monodendrons and Dendrimers

  摘要：

  Three generations of bithiophenesilane monodendrons and dendrimers consisting of 3-45 2,2'-bithiene-5,5'-diyl units were synthesized by means of effective coupling reactions between the corresponding bithienyllithium derivatives and chlorosilanes. These compounds show efficient photoluminescence in the violet-blue region, the quantum yield of which is 5-15 times higher than that for the parent bithiophene or bithiophenesilanes.

  DOI：

  10.1021/ol800811a

文献信息

• Synthesis and properties of a new luminescent oligoarylsilane dendrimer
  作者：Marina S. Polinskaya、Oleg V. Borshchev、Yuriy N. Luponosov、Nikolay M. Surin、Aziz M. Muzafarov、Sergei A. Ponomarenko

  DOI：10.1016/j.mencom.2011.03.010

  日期：2011.3

  An oligoarylsilane dendrimer containing peripheral 2,2 ’ -bithienyl groups and bis(2,2 ’ -bithien-5-yl)-1,4-phenylene fragments as the central moieties of the molecule has been synthesized; it exhibited efficient intramolecular energy transfer and a high quantum efficiency of luminescence.

  合成了含有周边2，2′-联噻吩基和双（2，2′-联噻吩-5-基）-1，4-亚苯基片段作为分子中心部分的低聚芳基硅烷树枝状大分子。它表现出有效的分子内能量转移和高的发光量子效率。
• Bithiophenesilane-Based Dendronized Polymers: Facile Synthesis and Properties of Novel Highly Branched Organosilicon Macromolecular Structures
  作者：S. A. Ponomarenko、N. N. Rasulova、Y. N. Luponosov、N. M. Surin、M. I. Buzin、I. Leshchiner、S. M. Peregudova、A. M. Muzafarov

  DOI：10.1021/ma2024045

  日期：2012.2.28

  The synthesis of two novel bithiophenesilane-based dendronized polymers by a chain growth Kumada polymerization, their molecular properties in dilute solutions and thermal properties in the bulk are described and compared with those of bithiophenesilane dendrimers. GPC equipped with a dual light scattering detector has shown that the polymers exhibit narrow polydispersity indices (PDI = 1.22-1.23) and have a weight-average polymerization degree of 44 for P1 and 30 for P2, which correspond to 88 and 120 bithiophenesilane fragments, respectively. Spectral-luminescent investigations showed that both polymers among with the bithiophenesilanes contain from 1 to 4 terthiophenesilane fragments in every macromolecule, which leads to the so-called "dendritic molecular antenna" effect. The intramolecular energy transfer efficiency was measured to be SO and 70% for polymers P1 and P2 respectively, which, alongside with the results of viscometric studies, points out to the compact conformation of these macromolecules in solution, which is close to those of bithiophenesilane dendrimers.