1,6-dibromo-3,3,4,4,5,5-hexafluorocyclopenta[c]thiophene | 909533-91-1

• 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: 1,6-dibromo-3,3,4,4,5,5-hexafluorocyclopenta[c]thiophene
• 英文别名: 2,5-Dibromo-3,4-(1,1,2,2,3,3-hexafluoro-1,3-propanediyl)thiophene；1,3-dibromo-4,4,5,5,6,6-hexafluorocyclopenta[c]thiophene
• CAS: 909533-91-1
• 化学式: C₇Br₂F₆S
• 分子量: 389.941
• InChiKey: DKQVUHZXAHSRPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,6-dibromo-3,3,4,4,5,5-hexafluorocyclopenta[c]thiophene 、 三异丙基氯硅烷 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以83%的产率得到(3-Bromo-4,4,5,5,6,6-hexafluorocyclopenta[c]thiophen-1-yl)-tri(propan-2-yl)silane
  参考文献：
  名称：

  Electronegative Oligothiophenes Fully Annelated with Hexafluorocyclopentene:  Synthesis, Properties, and Intrinsic Electron Mobility

  摘要：

  Synthesis of hexafluorocyclopenta[c]thiophene-repeated oligothiophenes up to 6-mer has been accomplished. The photophysical and electrochemical properties of these oligomers unambiguously exemplify marked electronegative character without disrupting the effective conjugation. The combination of time-resolved microwave conductivity and transient optical spectroscopy measurements of the 6-mer revealed the intrinsic electron mobility to be as high as 2.0 x 10(-1) cm(2) V-1 S-1.

  DOI：

  10.1021/ol703016g
• 作为产物：
  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

文献信息

• EP1857452
  申请人：——

  公开号：——

  公开（公告）日：——
• Condensation Compound Between Fluorinated Cyclopentane Ring and Aromatic Ring, and Process for Producing the Same
  申请人：Ie Yutaka

  公开号：US20080207922A1

  公开（公告）日：2008-08-28

  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.
• Polymer Comprising Unit Comprising Fluorocyclopentane Ring Fused With Aromatic Ring and Organic Thin Film and Organic Thin Film Element Both Comprising the Same
  申请人：Ie Yutaka

  公开号：US20080302419A1

  公开（公告）日：2008-12-11

  A polymer comprising a repeating unit represented by the following general formula (I). (In the formula, Ar 1 represents a divalent aromatic hydrocarbon or divalent heterocyclic group, X 1 , Y 1 , X 2 and Y 2 each independently represent a fluorine atom or alkylthio group, and X 1 and Y 1 and X 2 and Y 2 may together form a carbonyl or thiocarbonyl group with their bonding carbon atom.)
• CONDENSATION COMPOUND BETWEEN FLUORINATED CYCLOPENTANE RING AND AROMATIC RING, AND PROCESS FOR PRODUCING THE SAME
  申请人：IE Yutaka

  公开号：US20110213162A1

  公开（公告）日：2011-09-01

  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.
• US7932347B2
  申请人：——

  公开号：US7932347B2

  公开（公告）日：2011-04-26