2,6-bis(trimethylsilyl)benzo[1,2-b:4,5-b']dithiophene | 872513-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,6-bis(trimethylsilyl)benzo[1,2-b:4,5-b']dithiophene
• 英文别名: Trimethyl-(2-trimethylsilylthieno[2,3-f][1]benzothiol-6-yl)silane
• CAS: 872513-79-6
• 化学式: C₁₆H₂₂S₂Si₂
• 分子量: 334.654
• InChiKey: UFAJLBYUYDVOMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  191-192 °C(Solv: hexane (110-54-3))
• 沸点：
  424.8±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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-bis(trimethylsilyl)benzo[1,2-b:4,5-b']dithiophene 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到2,6-二碘苯并[1,2-b:4,5-b']二噻吩
  参考文献：
  名称：

  Molecular Modification of 2,6-Diphenylbenzo[1,2-b:4,5-b′]dichalcogenophenes by Introduction of Strong Electron-withdrawing Groups: Conversion from p- to n-Channel OFET Materials

  摘要：

  2,6-Diphenylbenzo[1,2-b:4,5-b′]dithiophene (DPh-BDT) 和 -diselenophene (DPh-BDS) 作为 p 沟道半导体材料，通过在所附苯基中引入氟基、氰基或三氟甲基进行了改性。在对使用这些改性化合物制造的有机场效应晶体管进行检查时发现，三氟甲基取代的 DPh-BDT 和 BDS 衍生物可用作 n 沟道半导体，电子迁移率分别高达 0.044 和 0.10 cm2 V-1 s-1。

  DOI：

  10.1246/cl.2006.1200
• 作为产物：
  描述：

  1,4-二溴-2,5-二碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 叔丁基锂 、 二异丙胺 作用下， 以 乙醚 、 正戊烷 、 苯 为溶剂， 反应 1.25h， 生成 2,6-bis(trimethylsilyl)benzo[1,2-b:4,5-b']dithiophene
  参考文献：
  名称：

  Facile Synthesis, Structure, and Properties of Benzo[1,2-b:4,5-b‘]dichalcogenophenes

  摘要：

  A general and convenient synthesis of benzo[1,2-b:4,5-b']-dichalcogenophenes including the thiophene (BDT, 1), selenophene (BDS, 2), and tellurophene (BDTe, 3) homologues is developed. Thus synthesized heterocycles are structurally characterized by single-crystal X-ray analysis, and all three homologues are isostructural with one another. They all have completely planar molecular structures packed in a herringbone arrangement. Their physicochemical properties were also elucidated by means of cyclic voltammetry (CV) and LTV-vis spectra.

  DOI：

  10.1021/jo051812m

文献信息

• Photochemical stability of π-conjugated polymers for polymer solar cells: a rule of thumb
  作者：Matthieu Manceau、Eva Bundgaard、Jon E. Carlé、Ole Hagemann、Martin Helgesen、Roar Søndergaard、Mikkel Jørgensen、Frederik C. Krebs

  DOI：10.1039/c0jm03105d

  日期：——

  A comparative photochemical stability study of a wide range of π-conjugated polymers relevant to polymer solar cells is presented. The behavior of each material has been investigated under simulated sunlight (1 sun, 1000 W m−2, AM 1.5G) and ambient atmosphere. Degradation was monitored during ageing combining UV-visible and infrared spectroscopies. From the comparison of the collected data, the influence of the polymer chemical structure on its stability has been discussed. General rules relative to the polymer structure–stability relationship are proposed.

  本文介绍了一项广泛的相关于聚合物太阳能电池的π共轭聚合物的光化学稳定性比较研究。在模拟太阳光（1个太阳，1000 W/m²，AM 1.5G）和常温大气条件下，研究了每种材料的行为。通过结合紫外-可见光谱和红外光谱监测了材料在老化过程中的降解情况。从收集的数据比较中，讨论了聚合物化学结构对其稳定性的影响。提出了一些关于聚合物结构与稳定性关系的普遍规律。
• Benzodichalcogenophenes with Perfluoroarene Termini
  作者：Yongfeng Wang、Sean R. Parkin、Mark D Watson

  DOI：10.1021/ol801569m

  日期：2008.10.16

  Benzodichalcogenophenes are functionalized at their termini via SNAr reactions of their bismetalates with perfluoroarenes. The identities of X, Y, and W are varied to study the effects on LUMO energy levels and crystallization motif. X-ray crystallography reveals that nearly all new derivatives crystallize with coplanar ring systems within slipped 1D or 2D pi-stacks.
• Facile Synthesis, Structure, and Properties of Benzo[1,2-<i>b</i>:4,5-<i>b</i>‘]dichalcogenophenes
  作者：Kazuo Takimiya、Yasushi Konda、Hideaki Ebata、Naoto Niihara、Tetsuo Otsubo

  DOI：10.1021/jo051812m

  日期：2005.12.1

  A general and convenient synthesis of benzo[1,2-b:4,5-b']-dichalcogenophenes including the thiophene (BDT, 1), selenophene (BDS, 2), and tellurophene (BDTe, 3) homologues is developed. Thus synthesized heterocycles are structurally characterized by single-crystal X-ray analysis, and all three homologues are isostructural with one another. They all have completely planar molecular structures packed in a herringbone arrangement. Their physicochemical properties were also elucidated by means of cyclic voltammetry (CV) and LTV-vis spectra.
• Molecular Modification of 2,6-Diphenylbenzo[1,2-<i>b</i>:4,5-<i>b</i>′]dichalcogenophenes by Introduction of Strong Electron-withdrawing Groups: Conversion from p- to n-Channel OFET Materials
  作者：Kazuo Takimiya、Yoshihito Kunugi、Hideaki Ebata、Tetsuo Otsubo

  DOI：10.1246/cl.2006.1200

  日期：2006.10

  2,6-Diphenylbenzo[1,2-b:4,5-b′]dithiophene (DPh-BDT) and -diselenophene (DPh-BDS) as p-channel semiconducting materials were modified by introducing fluoro, cyano, or trifluoromethyl groups into the attached phenyl moieties. On examination of organic field-effect transistors fabricated using these modified compounds, the trifluoromethyl-substituted DPh-BDT and BDS derivatives were found to act as n-channel semiconductors with high electron mobilities of 0.044 and 0.10 cm2 V−1 s−1, respectively.

  2,6-Diphenylbenzo[1,2-b:4,5-b′]dithiophene (DPh-BDT) 和 -diselenophene (DPh-BDS) 作为 p 沟道半导体材料，通过在所附苯基中引入氟基、氰基或三氟甲基进行了改性。在对使用这些改性化合物制造的有机场效应晶体管进行检查时发现，三氟甲基取代的 DPh-BDT 和 BDS 衍生物可用作 n 沟道半导体，电子迁移率分别高达 0.044 和 0.10 cm2 V-1 s-1。