diethyl 2,3-bis(4-bromobenzoyl)succinate | 1073467-80-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: diethyl 2,3-bis(4-bromobenzoyl)succinate
• 英文别名: Diethyl 2,3-bis(4-bromobenzoyl)butanedioate
• CAS: 1073467-80-7
• 化学式: C₂₂H₂₀Br₂O₆
• 分子量: 540.205
• InChiKey: DJOMLNAORFWKCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2,3-bis(4-bromobenzoyl)succinate 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 氯仿 为溶剂， 生成 3,6-bis(4-bromophenyl)-2,5-bis(2,6-dimethoxy-4-tridecylphenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Highly Luminescent Encapsulated Narrow Bandgap Polymers Based on Diketopyrrolopyrrole

  摘要：

  We present the synthesis and characterization of a series of encapsulated diketopyrrolopyrrole red-emitting conjugated polymers. The novel materials display extremely high fluorescence quantum yields in both solution (>70%) and thin film (>20%). Both the absorption and emission spectra show clearer, more defined features compared to their naked counterparts demonstrating the suppression of inter and intramolecular aggregation. We find that the encapsulation results in decreased energetic disorder and a dramatic increase in backbone colinearity as evidenced by scanning tunnelling microscopy. This study paves the way for diketopyrrolopyrrole to be used in emissive solid state applications and demonstrates a novel method to reduce structural disorder in conjugated polymers.

  DOI：

  10.1021/jacs.7b13447
• 作为产物：
  描述：

  (4-溴苯甲酰)乙酸乙酯 在 ammonium cerium (IV) nitrate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 0.25h， 以35%的产率得到diethyl 2,3-bis(4-bromobenzoyl)succinate
  参考文献：
  名称：

  硝酸铈 (IV) 铵氧化偶联 1,3-二羰基化合物

  摘要：

  描述了一种使用硝酸铈铵在 CH3CN/CH3OH/H2O 中进行 1,3-二羰基化合物分子间偶联的快速、温和且高效的方法。该过程为合成 1,4-二酮衍生物提供了一种简便的方法，收率高达 96%，并为硝酸铈铵介导的氧化机制提供了有力证据。

  DOI：

  10.1080/00397910903161876

文献信息

• Oxidative Coupling of 1,3-Dicarbonyl Compounds by Cerium(IV) Ammonium Nitrate
  作者：Jianan Song、Hao Zhang、Xianjun Chen、Xinsheng Li、Dongcheng Xu

  DOI：10.1080/00397910903161876

  日期：2010.5.19

  for the intermolecular coupling of 1,3-dicarbonyl compounds using cerium ammonium nitrate in CH3CN/CH3OH/H2O has been described. The procedure provided a convenient method for the synthesis of 1,4-diketone derivatives with excellent yields (up to 96%) and powerful evidence for the oxidation mechanism mediated by cerium ammonium nitrate.

  描述了一种使用硝酸铈铵在 CH3CN/CH3OH/H2O 中进行 1,3-二羰基化合物分子间偶联的快速、温和且高效的方法。该过程为合成 1,4-二酮衍生物提供了一种简便的方法，收率高达 96%，并为硝酸铈铵介导的氧化机制提供了有力证据。
• 一种可见光催化的1,3-二羰基类化合物脱氢 自偶联的方法
  申请人：南京工业大学

  公开号：CN108440291B

  公开（公告）日：2020-08-28

  本发明公开了一种可见光催化的1，3‑二羰基类化合物脱氢自偶联的方法，包括以下步骤：(1)将光催化剂、过氧化物、1，3‑二羰基类化合物溶解在溶剂中，并加入1，4‑二氧六环得到反应液；(2)用可见光照射所述步骤(1)中得到的反应液；待反应完成后分离得到1，3‑二羰基类化合物脱氢自偶联产物。本发明采用的可见光催化，实现了在较温和条件下对二羰基类化合物的偶联反应，响应了当前绿色化学的理念，以更为科学、环保的方法完成了二羰基化合物的偶联。
• Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP): Synthesis, optical and electronic properties
  作者：Kai Zhang、Bernd Tieke、John C. Forgie、Filipe Vilela、John A. Parkinson、Peter J. Skabara

  DOI：10.1016/j.polymer.2010.10.054

  日期：2010.12

  A series of 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) derivatives carrying thienyl-, 3,4-ethylenedioxy-thienyl- (EDOT-) and 3,4-ethylenedithiathienyl- (EDTf-) substituent groups have been synthesized and electrochemically polymerized. The polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. It was found that the growth of the polymers proceeded as random coupling of the thiophene groups in the 2-,3-,5-, and 6-positions of the DPP chromophore. In the cross-linked polymers, conjugated sequences were only built through coupling of thiophene groups in 3,6-positions, and separated by non-conjugated sequences through coupling with thiophene units in other positions of the DPP core. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly Luminescent Encapsulated Narrow Bandgap Polymers Based on Diketopyrrolopyrrole
  作者：Anastasia Leventis、Jeroen Royakkers、Alexandros G. Rapidis、Niall Goodeal、Merina K. Corpinot、Jarvist M. Frost、Dejan-Krešimir Bučar、Matthew Oliver Blunt、Franco Cacialli、Hugo Bronstein

  DOI：10.1021/jacs.7b13447

  日期：2018.2.7

  We present the synthesis and characterization of a series of encapsulated diketopyrrolopyrrole red-emitting conjugated polymers. The novel materials display extremely high fluorescence quantum yields in both solution (>70%) and thin film (>20%). Both the absorption and emission spectra show clearer, more defined features compared to their naked counterparts demonstrating the suppression of inter and intramolecular aggregation. We find that the encapsulation results in decreased energetic disorder and a dramatic increase in backbone colinearity as evidenced by scanning tunnelling microscopy. This study paves the way for diketopyrrolopyrrole to be used in emissive solid state applications and demonstrates a novel method to reduce structural disorder in conjugated polymers.