5,5'-dibromo-2,2'-biselenophene | 116886-64-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5,5'-dibromo-2,2'-biselenophene
• 英文别名: 2-bromo-5-(5-bromoselenophen-2-yl)selenophene
• CAS: 116886-64-7
• 化学式: C₈H₄Br₂Se₂
• 分子量: 417.848
• InChiKey: LJVJAPOMEYOWRT-UHFFFAOYSA-N

物化性质

• 沸点：
  390.5±37.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  5,5'-dibromo-2,2'-biselenophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二硫化碳 、 氯仿 、 溶剂黄146 为溶剂， 以73%的产率得到3,3',5,5'-tetrabromo-2,2'-biselenophene
  参考文献：
  名称：

  Selenophene-TCNQ 的广泛共轭同系物作为新的电子受体

  摘要：

  5,5'-双(二氰基亚甲基)-5,5'-二氢-2,2'-双硒吩、其3,3'-二溴衍生物和5,5"-双(二氰基亚甲基)-5,5"-二氢-2,2':5',2"-萜硒酚已被合成为硒酚-TCNQ的广泛共轭同系物。3,3'-二溴化合物比硒酚-TCNQ 或其他扩展的同系物具有更好的接受特性，并且可以形成高导电分子复合物。

  DOI：

  10.1246/cl.1988.1179
• 作为产物：
  描述：

  2,5-二溴硒酚 在 正丁基锂 、 copper dichloride 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 5.5h， 以57%的产率得到5,5'-dibromo-2,2'-biselenophene
  参考文献：
  名称：

  Fluorinated biselenophene-naphthalenediimide copolymers for efficient all-polymer solar cells

  摘要：

  Biselenophene (BS) is generally considered as a promising building block for constructing organic semiconductors, and the 3-positions of selenophene in BS offer a great opportunity for further structural modification. Herein, a novel fluorinated biselenophene, 3,3'-difluoro-2,2'-biselenophene (BSF), was designed and synthesized successfully, and subsequently incorporated into a polymer backbone leading to the resulting polymer PNDIBSF. The polymer backbone planarity was significantly improved via the enhanced intramolecular noncovalent Se center dot center dot center dot F coulombic interactions. Meanwhile, the electronic structure of the polymer was effectively tuned by the high electronegativity of F atoms. All-polymer solar cells (all-PSCs) with J71 and PNDIBSF as polymer donor and acceptor achieved power conversion efficiency (PCE) of 5.20%. In comparsion, all-PSCs based on the non-fluorinated analogue polymer acceptor (PNDIBS) had low PCE of 2.74%. The results demonstrated that BSF is a promising building block for constructing polymer acceptor in all-PSCs, and the fluorination offers a sufficient strategy for further improving performance of selenophene-based polymer semiconductors.

  DOI：

  10.1016/j.dyepig.2020.108721

文献信息

• Syntheses of 2-(Pentafluorophenyl)thiophene Derivatives via the Palladium-Catalyzed Suzuki Reaction
  作者：Kazuo Takimiya、Naoto Niihara、Tetsuo Otsubo

  DOI：10.1055/s-2005-865335

  日期：——

  Various bis(pentafluorophenyl)-substituted thiophene and selenophene derivatives are effectively synthesized by the palladium-catalyzed Suzuki reaction using pentafluorophenyl boronic acid.

  通过钯催化的 Suzuki 反应，使用五氟苯基硼酸有效地合成了各种双（五氟苯基）取代的噻吩和硒吩衍生物。
• Synthesis and Characterization of Fluorene-Based Conjugated Polymers Containing Thiophene Derivatives in Main Chain
  作者：Sang Kyu Lee、Young Kwan Jung、Won Suk Shin、Hong-Ku Shim、Sang-Jin Moon

  DOI：10.1080/15421401003604286

  日期：2010.4.13

  Three novel alternating copolymers containing 9,9-dioctylfluorene and thiophene derivatives, poly[(9,9-dioctylfluorene-2,7-diyl)-alt-(4,4'-bis(3 ''-hexyl-2 '' thienyl)-biphenyl-5 '',5 ''-diyl)] (P1), poly[(9,9-dioctylfluorene-2,7-diyl)-alt-(5,5'-bis (3 ''-hexyl-2 '' thienyl)-2,2'-bithiophenyl-5 '',5 ''-diyl)] (P2), and poly[(9,9-dioctylfluorene-2,7-diyl)-alt-(5,5'-bis(3 ''-hexyl-2 '' thienyl)-2,2'-biselenophenyl-5 '',5 ''-diyl)] (P3) were synthesized by a palladium-catalyzed Suzuki polymerization. The synthesis, thermal stability, as well as the optical and electrochemical properties of these polymers are systematically investigated. The polymers were thermally stable up to 400 degrees C, and readily soluble in common organic solvent. The absorption and emission maxima of the copolymers varied according to the type of incorporated aromatic group (thiophene, selenophene, or phenylene).
• 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.
• Oligoselenophenes (n and p Type): Synthesis and Properties
  作者：B. Mondal、M. Bendikov、U. Kanti Roy

  DOI：10.1134/s1070363219090287

  日期：2019.9

  An array of semiconducting oligoselenophenes (n and p types), up to hexamer units, has been synthesized by the double Stille coupling methods using tetrakis(triphenylphosphine)palladium(0) as a catalyst. A series of semiconducting oligomers (n and p types) containing mixed hetero-units (hexamers of thiophene and selenophene) have been also synthesized using the Stille coupling reaction. Their thermal properties are systematically studied and compared with those of pi-conjugated thiophene based oligomers using DSC and TGA. The field-effect mobility of synthesized n and p type oligomers is analyzed.
• OGURA, FUMIO;OTSUBO, TEHTSUO;YASUAKI, JOSIO;YUI, KODZI
  作者：OGURA, FUMIO、OTSUBO, TEHTSUO、YASUAKI, JOSIO、YUI, KODZI

  DOI：——

  日期：——