2,6-bis(trimethylsilyl)benzo[1,2-b:4,5-b']diselenophene | 872513-80-9

• 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: 2,6-bis(trimethylsilyl)benzo[1,2-b:4,5-b']diselenophene
• 英文别名: Trimethyl-(2-trimethylsilylselenopheno[2,3-f][1]benzoselenol-6-yl)silane
• CAS: 872513-80-9
• 化学式: C₁₆H₂₂Se₂Si₂
• 分子量: 428.442
• InChiKey: HSEXKFUPHNBDEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  181-184 °C(Solv: hexane (110-54-3))
• 沸点：
  442.9±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,6-bis(trimethylsilyl)benzo[1,2-b:4,5-b']diselenophene 在 四(三苯基膦)钯 potassium phosphate 、 一氯化碘 、 silver(l) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 2,6-bis(4-cyanophenyl)benzo[1,2-b:4,5-b']diselenophene
  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']diselenophene
  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

• 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。