1,3-dibromo-cyclopenta[c]thiophene-4,6-dione | 246232-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dibromo-cyclopenta[c]thiophene-4,6-dione
• 英文别名: 1,3-dibromo-4H-cyclopenta[c]thiophene-4,6(5H)-dione；1,3-dibromocyclopenta[c]thiophene-4,6-dione
• CAS: 246232-37-1
• 化学式: C₇H₂Br₂O₂S
• 分子量: 309.966
• InChiKey: BZERWMXWDMMPRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-cyclopenta[c]thiophene-4,6-dione 在 N-fluoro-6-(trifluoromethyl)pyridinium-2-sulfonate 、 boron trifluoride diacetate 、 氟化氢吡啶 作用下， 以 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 10.0h， 生成 1,6-dibromo-3,3,4,4,5,5-hexafluorocyclopenta[c]thiophene
  参考文献：
  名称：

  Electronegative Oligothiophenes Based on a Hexafluorocyclopentene-Annelated Thiophene Unit

  摘要：

  [GRAPHICS]The synthesis of hexafluorocyclopenta[c] thiophene and its based oligothiophenes is described. The effectiveness of a hexafluorocyclopentene unit to lower the LUMO level without disturbing the effective conjugation could be unambiguously clarified by spectroscopic measurements and X-ray analysis.

  DOI：

  10.1021/ol062238j
• 作为产物：
  描述：

  1,3-dibromo-4-oxo-5,6-dihydro-4H-cyclopentathien-6-ylammonium chloride 在 chromium(VI) oxide 、 air 、 硫酸 、 水 、 sodium nitrite 作用下， 以 丙酮 为溶剂， 反应 24.25h， 生成 1,3-dibromo-cyclopenta[c]thiophene-4,6-dione
  参考文献：
  名称：

  First Synthesis of Isothianinhydrin, the Second Thiophene Isostere of Ninhydrin

  摘要：

  报告首次合成了茚三酮的噻吩异构体异噻吩海德林（5,5-二羟基-5,6-二氢-4H-环戊并[c]噻吩-4,6-二酮）及其溴和氯衍生物，并初步评估了它们在指纹检测领域的用途。

  DOI：

  10.1055/s-1999-2845

文献信息

• 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
  申请人：PnH tech (주)피엔에이치테크(120100135796) Corp. No ▼ 131111-0237931BRN ▼129-86-36614

  公开号：KR101626523B1

  公开（公告）日：2016-06-01

  유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자가 개시된다. 이에 의하여, 전기적 안정성 및 정공 수송능력이 우수하며, 삼중항 상태 에너지가 높아 인광발광재료의 발광효율을 향상시킬 수 있는 호스트 및 정공수송물질로 사용할 수 있는 유기전계발광소자용 화합물 및 유기전계발광소자를 제공할 수 있다.

  提供有机电致发光器件用化合物及包含该化合物的有机电致发光器件。因此，可以提供用作宿主和正电荷传输材料，具有优异的电学稳定性和正电荷传输能力，三重态能量高，可以提高光致发光材料的发光效率的有机电致发光器件用化合物和有机电致发光器件。
• SEMICONDUCTING POLYMERS AND TERNARY BLENDS THEREOF
  申请人：THE UNIVERSITY OF CHICAGO

  公开号：US20160204348A1

  公开（公告）日：2016-07-14

  Semiconducting photovoltaic polymers and compositions are disclosed. The polymers and compositions exhibit increased power conversion efficiency in solar cells and other applications.

  本发明公开了半导体光伏聚合物和组合物。这些聚合物和组合物在太阳能电池和其他应用中表现出更高的功率转换效率。
• Encapsulated oligothiophenes having electron-affinity characteristics
  作者：Masaru Endou、Yutaka Ie、Yoshio Aso

  DOI：10.1039/c1cc14994f

  日期：——

  Oligothiophenes composed of dioxocyclopenta[c]thiophene bearing bulky bis(di-t-butylphenyl) groups were designed and synthesized to develop molecular wires having electron-transporting characteristics. Their effective conjugation, electron affinity, and encapsulation effects were investigated by photophysical and electrochemical measurements.

  设计并合成了由带有大双(二叔丁基苯基)基团的二氧代环五[c]噻吩组成的低聚噻吩，以开发具有电子传输特性的分子线。通过光物理和电化学测量研究了它们的有效共轭、电子亲和力和封装效应。
• Synthesis and Properties of Polymer Having Electronegative Terthiophene Pendants Based on Cyclopenta[<i>c</i>]thiophene
  作者：Yutaka Ie、Atsuki Yoshimura、Daisuke Takeuchi、Kohtaro Osakada、Yoshio Aso

  DOI：10.1246/cl.2011.1039

  日期：2011.9.5

  We have designed a new pendant-type polymer having an electronegative terthiophene at pendant positions. This polymer was successfully synthesized by the combination of Stille coupling reaction and...

  我们设计了一种新的悬垂型聚合物，在悬垂位置具有带电负性的三噻吩。该聚合物是通过Stille偶联反应和...
• CONDENSATION COMPOUND BETWEEN FLUORINATED CYCLOPENTANE RING AND AROMATIC RING, AND PROCESS FOR PRODUCING THE SAME
  申请人：OSAKA UNIVERSITY

  公开号：EP1857452A1

  公开（公告）日：2007-11-21

  A condensation compound of a fluorinated cyclopentane ring and an aromatic ring, which is useful, for example, for electronic materials, and a process for producing the same are provided. For instance, according to Scheme 1 below, a compound (68) containing a condensed structure formed of a hexafluorocyclopentane ring and an aromatic ring is synthesized. The aromatic ring is not limited to a thiophene ring but can be any ring and any substituent can be used. Thus a compound containing a condensed ring structure formed of a hexafluorocyclopentane ring and an aromatic ring, particularly, for instance, a thiophene ring, which was impossible to produce conventionally, can be produced easily with high yield. The compound of the present invention is particularly suitable to be applied to, for example, electronic materials or semiconductors. When it is polymerized and thereby the π-electronic conjugation is extended, it also is expected to be applied to, for example, n-type organic semiconductors and molecular wires that are indispensable for developing molecular electronics elements.

  本发明提供了一种可用于电子材料等的氟化环戊烷环和芳香环的缩合化合物及其生产工艺。例如，根据下面的方案 1，合成了一种含有六氟环戊烷环和芳香环缩合结构的化合物 (68)。芳香环不限于噻吩环，可以是任何环，也可以使用任何取代基。因此，包含由六氟环戊烷环和芳香环（尤其是噻吩环）形成的缩合环结构的化合物可以很容易地以高产率生产出来。本发明的化合物尤其适用于电子材料或半导体等领域。当它被聚合从而扩展了 π-电子共轭时，它也有望应用于例如开发分子电子元件所不可或缺的 n 型有机半导 体和分子线。