2,5-dibromo-4-(phenylcarbamoyl)thiophene-3-carboxylic acid | 1598412-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-dibromo-4-(phenylcarbamoyl)thiophene-3-carboxylic acid
• 英文别名: 2,5-Dibromo-4-(phenylcarbamoyl)thiophene-3-carboxylic acid
• CAS: 1598412-43-1
• 化学式: C₁₂H₇Br₂NO₃S
• 分子量: 405.066
• InChiKey: XWCOQARIJQKKGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dibromo-4-(phenylcarbamoyl)thiophene-3-carboxylic acid 在 氯化亚砜 作用下， 反应 12.0h， 生成 1,3-dibromo-5-phenylthieno[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  Fine tuning of frontier orbital energy levels in dithieno[3,2-b:2′,3′-d]silole-based copolymers based on the substituent effect of phenyl pendants

  摘要：

  A series of dithieno[3,2-b:2 ',3 '-d]silole-based pi-conjugated copolymers containing thieno[3,4-c]pyrrole-4,6-dione or thieno[3,4-b]thiophene units bearing 4-substituted phenyl pendants were synthesized and their thermal stability, optical properties and frontier orbital energy levels were systematically investigated. The introduction of electron-withdrawing substituents on the phenyl rings lowered their frontier orbital energy levels without deteriorating their thermal and optical properties. By replacing an electron-donating methoxy group with an electron-withdrawing trifluoromethyl group, both the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital energy levels of the polymers were deepened by more than 0.3 eV. A relatively linear relationship was observed between the HOMO energy levels and the Hammett substituent constants. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.03.021
• 作为产物：
  描述：

  4,6-二溴噻吩并[3,4-C]呋喃-1,3-二酮 、 苯胺 以 甲苯 为溶剂， 反应 24.0h， 生成 2,5-dibromo-4-(phenylcarbamoyl)thiophene-3-carboxylic acid
  参考文献：
  名称：

  Fine tuning of frontier orbital energy levels in dithieno[3,2-b:2′,3′-d]silole-based copolymers based on the substituent effect of phenyl pendants

  摘要：

  A series of dithieno[3,2-b:2 ',3 '-d]silole-based pi-conjugated copolymers containing thieno[3,4-c]pyrrole-4,6-dione or thieno[3,4-b]thiophene units bearing 4-substituted phenyl pendants were synthesized and their thermal stability, optical properties and frontier orbital energy levels were systematically investigated. The introduction of electron-withdrawing substituents on the phenyl rings lowered their frontier orbital energy levels without deteriorating their thermal and optical properties. By replacing an electron-donating methoxy group with an electron-withdrawing trifluoromethyl group, both the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital energy levels of the polymers were deepened by more than 0.3 eV. A relatively linear relationship was observed between the HOMO energy levels and the Hammett substituent constants. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.03.021

文献信息

• PREPARATION AND PROPERTIES OF PERYLENE AND NAPHTHALENE POLYIMIDES AND OTHER RIGID CONJUGATED POLYMERS VIA SOLUBLE AMIDE-ESTER PRECURSOR
  申请人：Colorado School of Mines

  公开号：US20140209879A1

  公开（公告）日：2014-07-31

  This invention relates to a method for making soluble precursors to imides, polyimides, and polymers containing imide groups, and a method of making thin films of the same by solution casting and then removing the solubilizing group to produce thermally stable and insoluble materials.

  本发明涉及一种制备可溶性咪唑、聚咪唑和含有咪唑基团的聚合物的前体的方法，以及通过溶液铸造并去除溶解基团来制备热稳定和不溶性材料的薄膜的方法。
• Method of forming rigid imide material from soluble amide ester functionalized precursors
  申请人：Colorado School of Mines

  公开号：US09355787B2

  公开（公告）日：2016-05-31

  This invention relates to a method for making soluble precursors to imides, polyimides, and polymers containing imide groups, and a method of making thin films of the same by solution casting and then removing the solubilizing group to produce thermally stable and insoluble materials.

  本发明涉及一种制备咪唑、聚咪唑和含有咪唑基团的聚合物的可溶性前体的方法，以及通过溶液浇铸然后去除溶解化基团制备热稳定和不溶性材料的薄膜的方法。
• US9355787B2
  申请人：——

  公开号：US9355787B2

  公开（公告）日：2016-05-31
• Fine tuning of frontier orbital energy levels in dithieno[3,2-b:2′,3′-d]silole-based copolymers based on the substituent effect of phenyl pendants
  作者：Tomoyuki Ikai、Tomoya Kudo、Masahiro Nagaki、Tomoyuki Yamamoto、Katsuhiro Maeda、Shigeyoshi Kanoh

  DOI：10.1016/j.polymer.2014.03.021

  日期：2014.4

  A series of dithieno[3,2-b:2 ',3 '-d]silole-based pi-conjugated copolymers containing thieno[3,4-c]pyrrole-4,6-dione or thieno[3,4-b]thiophene units bearing 4-substituted phenyl pendants were synthesized and their thermal stability, optical properties and frontier orbital energy levels were systematically investigated. The introduction of electron-withdrawing substituents on the phenyl rings lowered their frontier orbital energy levels without deteriorating their thermal and optical properties. By replacing an electron-donating methoxy group with an electron-withdrawing trifluoromethyl group, both the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital energy levels of the polymers were deepened by more than 0.3 eV. A relatively linear relationship was observed between the HOMO energy levels and the Hammett substituent constants. (C) 2014 Elsevier Ltd. All rights reserved.