2,6-dibromo-4,4-diphenyl dithienosilole | 207742-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,6-dibromo-4,4-diphenyl dithienosilole
• 英文别名: 4,4'-diphenyl-2,6-dibromo-dithieno-[3,2-b:2',3'-d]silole；4,10-Dibromo-7,7-diphenyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 207742-45-8
• 化学式: C₂₀H₁₂Br₂S₂Si
• 分子量: 504.341
• InChiKey: IGICUPFPOUHFQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-4,4-diphenyl dithienosilole 在 正丁基锂 、 水 作用下， 以 乙醚 为溶剂， 以77%的产率得到7,7-Diphenyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene
  参考文献：
  名称：

  Synthesis and properties of dithienosiloles

  摘要：

  A series of dithienosilole derivatives were synthesized and some of their properties were investigated. UV spectra of dithienosiloles show absorption bands around 350 nm and their cyclic voltammograms display oxidation peaks at about 1.2 V vs. SCE. Nickel-catalyzed coupling of 2,6-dibromodithienosilole with the diGrignard reagent prepared from bis(5-bromothienyl)tetraethyldisilane afforded an alternating polymer composed of a 2,6-dithienyldithienosilole system and tetraethyldisilanylene unit. When the polymer film was doped with FeCl3 vapor, the film became conducting with the maximum conductivity of 7.0 x 10(-3) S/cm. (C) 1998 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(97)00643-8
• 作为产物：
  描述：

  3,3’-二溴-5,5’-双(三甲基硅基)-2,2’-联噻吩 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2,6-dibromo-4,4-diphenyl dithienosilole
  参考文献：
  名称：

  Highly luminescent π-conjugated dithienometalloles: photophysical properties and their application in organic light-emitting diodes

  摘要：

  我们已公开了一系列包含Ge、Si、P和S原子作为桥连中心的双环[3,2-b:2',3'-d]金属啉衍生物的异芳环化π-共轭体系的荧光光物理性质和电致发光性质。通过紫外/可见光谱、荧光光谱、瞬态荧光测量和密度泛函理论计算，系统地研究了异芳环化结构对其光物理性质的影响。所有这些化合物在溶液和掺杂的薄膜中都表现出明亮的荧光和高量子产率。此外，采用双噻吩金属啉发射体的OLEDs在实际亮度下表现出高达约6%的外部量子效率。

  DOI：

  10.1039/c2jm33526c

文献信息

• Synthesis of dithienosilole-based highly photoluminescent donor–acceptor type compounds
  作者：Joji Ohshita、Yuta Tominaga、Daiki Tanaka、Yousuke Ooyama、Tomonobu Mizumo、Norifumi Kobayashi、Hideyuki Higashimura

  DOI：10.1039/c2dt32738d

  日期：——

  Highly photoluminescent acceptor–donor–acceptor (A–D–A) and donor–acceptor (D–A) type compounds with a dithienosilole unit as the donor and perfluorotolyl or dimesitylboryl group(s) as the acceptor were prepared by the reaction of lithiated dithienosilole derivatives with perfluorotoluene or fluorodimesitylborane, respectively. The resulting A–D–A and D–A type compounds showed red-shifted UV absorption and PL bands compared to those of simple dithienosiloles having no acceptor units, reported previously, and were highly photoluminescent in the solid state as well as in solution. Solvatochromic behaviour that would arise from the intramolecular donor–acceptor interaction were observed for the D–A type compounds with respect to the UV absorption and PL spectra. In addition, it was found that bis(dimesitylboryl)dithienosilole and (dimesitylboryl)(methylthio)dithienosilole responded to coexisting fluoride anions, leading to clear UV absorption and PL spectral changes in solutions.

  具有高光致发光性能的受体-给体-受体（A-D-A）和给体-受体（D-A）型化合物，以二噻吩并硅杂环戊二烯单元作为给体，全氟甲苯或二三甲苯硼烷基团作为受体，通过锂化的二噻吩并硅杂环戊二烯衍生物分别与全氟甲苯或氟代二三甲苯硼烷反应制备得到。与先前报道的不含受体单元的简单二噻吩并硅杂环戊二烯相比，得到的A-D-A和D-A型化合物显示出红移的紫外吸收和光致发光光谱，并且在固体状态和溶液中都具有高度的光致发光性能。对于D-A型化合物，观察到了由于分子内给体-受体相互作用而引起的溶剂化变色行为，表现在紫外吸收和光致发光光谱上。此外，发现双（二三甲苯硼烷基）二噻吩并硅杂环戊二烯和（二三甲苯硼烷基）（甲硫基）二噻吩并硅杂环戊二烯对共存的氟离子有响应，导致溶液中的紫外吸收和光致发光光谱发生明显变化。
• WO2008/109701
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and properties of new fluorene-containing copolymer via the catalytic dehydrocoupling reaction of 9,9-dipropargyl fluorene and 4,4′-diphenyl-2,6-dibromo-dithieno-[3,2-b:2′,3′-d]silole
  作者：Gab Yong Lee、Yeong-Soon Gal、Sang-Gu Lee

  DOI：10.1080/15421406.2016.1200925

  日期：2016.8.12

  New fluorene-containing copolymer was prepared via the catalytic dehydrocoupling reaction of 9,9-dipropargylfluorene and 4,4-diphenyl-2,6-dibromo-dithieno-[3,2-b:2,3-d]silole in 44% yield. The resulting polymer was completely soluble in common organic solvents. The thermal behaviors and optical properties of the resulting polymer were measured and discussed. The chemical structure of polymer was characterized by NMR, IR, and UV-visible spectroscopies. The polymer showed characteristic wide UV-visible absorption band and blue PL maximum value at 440nm, which is corresponding photon energy of 2.82eV. The quantum yield (6.44%) of poly(DPF-DTS) was found to be 5times higher than that of poly(DPF-bithiophene)).
• JP5847605
  申请人：——

  公开号：——

  公开（公告）日：——
• Highly luminescent π-conjugated dithienometalloles: photophysical properties and their application in organic light-emitting diodes
  作者：Ryosuke Kondo、Takuma Yasuda、Yu Seok Yang、Jun Yun Kim、Chihaya Adachi

  DOI：10.1039/c2jm33526c

  日期：——

  We have disclosed the photophysical and electroluminescent properties of a series of hetero-annulated π-conjugated dithieno[3,2-b:2′,3′-d]metallole derivatives incorporating Ge, Si, P, and S atoms as a bridging center. The influence of the hetero-annulated structures on their photophysical properties has been investigated systematically by UV/vis and photoluminescence (PL) spectroscopy, transient PL measurements, and DFT calculations. All these compounds show bright fluorescence with high quantum yields both in solutions and in doped thin films with a host matrix. Furthermore, the OLEDs employing the dithienometallole emitters exhibit high external quantum efficiencies of ∼6% at a practical brightness.

  我们已公开了一系列包含Ge、Si、P和S原子作为桥连中心的双环[3,2-b:2',3'-d]金属啉衍生物的异芳环化π-共轭体系的荧光光物理性质和电致发光性质。通过紫外/可见光谱、荧光光谱、瞬态荧光测量和密度泛函理论计算，系统地研究了异芳环化结构对其光物理性质的影响。所有这些化合物在溶液和掺杂的薄膜中都表现出明亮的荧光和高量子产率。此外，采用双噻吩金属啉发射体的OLEDs在实际亮度下表现出高达约6%的外部量子效率。