2,6-bis(trimethylsilyl)cyclopenta[2,1-b:3,4-b']diselenophen-4-one | 1277190-60-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis(trimethylsilyl)cyclopenta[2,1-b:3,4-b']diselenophen-4-one
• 英文别名: 4,10-Bis(trimethylsilyl)-3,11-diselenatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-7-one
• CAS: 1277190-60-9
• 化学式: C₁₅H₂₀OSe₂Si₂
• 分子量: 430.414
• InChiKey: MFGINOUQIXIGPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-bis(trimethylsilyl)cyclopenta[2,1-b:3,4-b']diselenophen-4-one 在 N-溴代丁二酰亚胺(NBS) 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 2,6-dibromocyclopenta[2,1-b:3,4-b']diselenophene-4-one
  参考文献：
  名称：

  Synthesis and Molecular Properties of Tricyclic Biselenophene-Based Derivatives with Nitrogen, Silicon, Germanium, Vinylidene, and Ethylene Bridges

  摘要：

  A new class of biselenophene-based materials including an sp(3)-silicon-bridged diselenosilole (DSS), an sp(3)-germanium-bridged diselenogermole (DSG), and an sp(3)-nitrogen-bridged diselenopyrrole (DSP) as well as an sp(2)-vinylidene-bridged dicyanodiselenofulvene (CDSF), a diacetylenediselenofulvene (ADSF), and a dioctylethylene-bridged benzodiselenophene (BDS) have been successfully synthesized and characterized. The bridging moieties play an important role in determining the optical and electrochemical properties. The six brominated derivatives are ready to construct various biselenophene-based conjugated materials with tunable properties for organic photovoltaics and field effect transistors.

  DOI：

  10.1021/ol502793e
• 作为产物：
  描述：

  3,3'-dibromo-5,5'-bis-trimethylsilanyl-2,2'-biselenophene 、 N,N-二乙基氯甲酰胺 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.33h， 生成 2,6-bis(trimethylsilyl)cyclopenta[2,1-b:3,4-b']diselenophen-4-one
  参考文献：
  名称：

  Synthesis and Molecular Properties of Tricyclic Biselenophene-Based Derivatives with Nitrogen, Silicon, Germanium, Vinylidene, and Ethylene Bridges

  摘要：

  A new class of biselenophene-based materials including an sp(3)-silicon-bridged diselenosilole (DSS), an sp(3)-germanium-bridged diselenogermole (DSG), and an sp(3)-nitrogen-bridged diselenopyrrole (DSP) as well as an sp(2)-vinylidene-bridged dicyanodiselenofulvene (CDSF), a diacetylenediselenofulvene (ADSF), and a dioctylethylene-bridged benzodiselenophene (BDS) have been successfully synthesized and characterized. The bridging moieties play an important role in determining the optical and electrochemical properties. The six brominated derivatives are ready to construct various biselenophene-based conjugated materials with tunable properties for organic photovoltaics and field effect transistors.

  DOI：

  10.1021/ol502793e

文献信息

• Mono- and Dicarbonyl-Bridged Tricyclic Heterocyclic Acceptors: Synthesis and Electronic Properties
  作者：Yulia A. Getmanenko、Chad Risko、Paul Tongwa、Eung-Gun Kim、Hong Li、Bhupinder Sandhu、Tatiana Timofeeva、Jean-Luc Brédas、Seth R. Marder

  DOI：10.1021/jo102502u

  日期：2011.4.15

  A series of trialkylsilyl-substituted 2,2'-dithiophene, 4,4'-di-n-hexy1-2,2'-dithiophene, 5,5'-dithiazole, and 2,2'-diselenophene with carbonyl (2a-d) and alpha-dicarbonyl bridges (3a-d) were prepared from readily available dihalides, using double lithiation followed by trapping with N,N-dimethylcarbamoyl chloride or diethyl oxalate (or N,N-dimethylpiperazine-2,3-dione), respectively. Cyclic voltammetry reveals that the first half-wave reduction potentials for this series of compounds span a wide range, from -1.87 to -0.97 V vs the ferrocene/ferrocenium couple at 0 V (0.1 M (Bu4NPF6)-Bu-n in THF). A significant increase of the first half-wave reduction potential (by 0.50-0.67 V) was observed on substitution of the monocarbonyl bridge with a-dicarbonyl. Adiabatic electron affinity (AEA, gas phase) trends determined via density functional theory (DFT) calculations are in good agreement with the electrochemical reduction potentials. UV vis absorption spectra across the series show a weak absorption band in the visible range, corresponding to the HOMO -> LUMO transition within a one-electron picture, followed by a more intense, high-energy transition (s). Single-crystal X-ray structural analyses reveal molecular packing features that balance the interplay of the presence of the bulky substituents, intermolecular pi-stacking interactions, and S center dot center dot center dot O intermolecular contacts, all of which affect the DFT-evaluated intermolecular electronic couplings and effective charge-carrier masses for the crystals of the tricyclic cores.
• Synthesis and Molecular Properties of Tricyclic Biselenophene-Based Derivatives with Nitrogen, Silicon, Germanium, Vinylidene, and Ethylene Bridges
  作者：Yu-Chieh Pao、Yung-Lung Chen、Yen-Ting Chen、Sheng-Wen Cheng、Yu-Ying Lai、Wen-Chia Huang、Yen-Ju Cheng

  DOI：10.1021/ol502793e

  日期：2014.11.7

  A new class of biselenophene-based materials including an sp(3)-silicon-bridged diselenosilole (DSS), an sp(3)-germanium-bridged diselenogermole (DSG), and an sp(3)-nitrogen-bridged diselenopyrrole (DSP) as well as an sp(2)-vinylidene-bridged dicyanodiselenofulvene (CDSF), a diacetylenediselenofulvene (ADSF), and a dioctylethylene-bridged benzodiselenophene (BDS) have been successfully synthesized and characterized. The bridging moieties play an important role in determining the optical and electrochemical properties. The six brominated derivatives are ready to construct various biselenophene-based conjugated materials with tunable properties for organic photovoltaics and field effect transistors.