1,3-dibromo-5,5-difluoro-4H-cyclopenta[c]thiophene-4,6(5H)-dione | 909533-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dibromo-5,5-difluoro-4H-cyclopenta[c]thiophene-4,6(5H)-dione
• 英文别名: 1,3-Dibromo-5,5-difluoro-5,6-dihydro-4H-cyclopenta[c]thiophene-4,6-dione；1,3-dibromo-5,5-difluorocyclopenta[c]thiophene-4,6-dione
• CAS: 909533-97-7
• 化学式: C₇Br₂F₂O₂S
• 分子量: 345.947
• InChiKey: MWOPKPMJGDUYIS-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  390.0±42.0 °C(Predicted)
• 密度：
  2.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 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：
  5

反应信息

• 作为反应物：
  描述：

  1,3-dibromo-5,5-difluoro-4H-cyclopenta[c]thiophene-4,6(5H)-dione 在 boron trifluoride diacetate 、 氟化氢吡啶 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 6.0h， 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-cyclopenta[c]thiophene-4,6-dione 在 N-fluoro-6-(trifluoromethyl)pyridinium-2-sulfonate 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以84%的产率得到1,3-dibromo-5,5-difluoro-4H-cyclopenta[c]thiophene-4,6(5H)-dione
  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

文献信息

• Electronegative Oligothiophenes Having Difluorodioxocyclopentene-annelated Thiophenes as Solution-processable n-Type OFET Materials
  作者：Yutaka Ie、Makoto Okabe、Yoshikazu Umemoto、Hirokazu Tada、Yoshio Aso

  DOI：10.1246/cl.2009.460

  日期：2009.5.5

  Solution-processable electronegative oligothiophenes bearing difluorodioxocyclopentene-annelated thiophenes have been synthesized. The electronic properties of the oligomers were investigated by absorption spectroscopy and electrochemical measurements. Their films fabricated by spin-coating showed typical n-channel OFET behavior.

  我们合成了含有二氟二氧环戊烯-沟道化噻吩的可溶液加工的负电性低聚噻吩。通过吸收光谱和电化学测量研究了这些低聚物的电子特性。通过旋涂法制造的薄膜显示出典型的 n 沟道 OFET 行为。
• 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。
• CONJUGATED COMPOUND, NITROGENATED CONDENSED-RING COMPOUND, NITROGENATED CONDENSED-RING POLYMER, ORGANIC THIN FILM, AND ORGANIC THIN FILM ELEMENT
  申请人：Osaka University

  公开号：EP2223918A1

  公开（公告）日：2010-09-01

  According to the first invention group there are provided conjugated compounds having two or more groups represented by the following formula (I) or the following formula (II): wherein one of Ar and Ar' represents a C6 or greater divalent aromatic hydrocarbon group and the other represents a C4 or greater divalent heterocyclic group, wherein the groups each may have a substituent, with the proviso that the groups as a whole contain no fluorine atoms, R1 and R2 each independently represent a hydrogen atom, a halogen atom or a monovalent group, and Ar" represents a trivalent aromatic hydrocarbon or trivalent heterocyclic group; when the conjugated compound has two or more groups represented by formula (I), the portion excluding these groups contain no fluorine atoms. According to the second group of the present invention there are provided nitrogen-containing fused-ring compounds represented by the following formula (α-I): in formula (α-I), R21 and R22 each independently represent a hydrogen atom, a halogen atom or an optionally substituted monovalent group, and Z21 and Z22 , each independently represent any one of the groups represented by the following formulas (α-i)-(α-ix); wherein R23, R24, R25 and R26 each independently represent a hydrogen atom, a halogen atom or a monovalent group, and R23 and R24 may bond together to form a ring, the left side and the right side of the group represented by formula (α-viii) may be interchanged.

  根据第一发明组，提供了具有两个或两个以上由下式（I）或下式（II）代表的基团的共轭化合物： 其中Ar和Ar'中的一个代表C6或更高的二价芳香烃基团，另一个代表C4或更高的二价杂环基团，其中各基团可有一个取代基，但各基团整体上不含氟原子，R1和R2各自独立地代表氢原子、卤素原子或一价基团，Ar "代表三价芳香烃或三价杂环基团；当共轭化合物具有两个或两个以上由式（I）表示的基团时，不包括这些基团的部分不含有氟原子。 根据本发明的第二组，提供了由下式（α-I）代表的含氮熔环化合物： 式(α-I)中，R21 和 R22 各自独立地代表氢原子、卤素原子或任选取代的一价基团，Z21 和 Z22 ，各自独立地代表下列式(α-i)-(α-ix)所代表的基团中的任一个； 其中 R23、R24、R25 和 R26 各自独立地代表氢原子、卤素原子或单价基团，且 R23 和 R24 可键合在一起形成环，式 (α-viii) 所代表基团的左侧和右侧可互换。
• Nitrogen-containing fused-ring compound, polymer comprising a nitrogen-containing fused-ring repeating unit, organic thin film, and organic thin film element
  申请人：SUMITOMO CHEMICAL CO., LTD.

  公开号：EP2520572A1

  公开（公告）日：2012-11-07

  The present invention provides nitrogen-containing fused-ring compounds represented by the following formula (α-I): in formula (α-I), R21 and R22 each independently represent a hydrogen atom, a halogen atom or an optionally substituted monovalent group, and Z21 and Z22 each independently represent any one of the groups represented by the following formulas (α-i)-(α-ix); wherein R23, R24, R25 and R26 each independently represent a hydrogen atom, a halogen atom or a monovalent group, and R23 and R24 may bond together to form a ring, the left side and the right side of the group represented by formula (α-viii) may be interchanged.

  本发明提供了由下式（α-I）表示的含氮熔环化合物： 式(α-I)中，R21和R22各自独立地代表氢原子、卤素原子或任选取代的一价基团，Z21和Z22各自独立地代表下式(α-i)-(α-ix)所代表的基团中的任一个； 其中 R23、R24、R25 和 R26 各自独立地代表氢原子、卤素原子或单价基团，且 R23 和 R24 可键合在一起形成环，式 (α-viii) 所代表基团的左侧和右侧可互换。