3,6-bis(5-bromofuran-2-yl)-1,2,4,5-tetrazine | 58884-46-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 3,6-bis(5-bromofuran-2-yl)-1,2,4,5-tetrazine
• CAS: 58884-46-1
• 化学式: C₁₀H₄Br₂N₄O₂
• 分子量: 371.975
• InChiKey: NNCBZPWHRPXSED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-bis(5-bromofuran-2-yl)-1,2,4,5-tetrazine 、 1-己基-1H-吡咯-2,5-二酮 以 二苯醚 为溶剂， 反应 16.0h， 以73%的产率得到1,4-bis(5-bromofuran-2-yl)-6-hexyl-5H-pyrrolo[3,4-d]pyridazine-5,7(6H)-dione
  参考文献：
  名称：

  [EN] DONOR-ACCEPTOR POLYMERS
  [FR] POLYMÈRES DONNEURS-ACCEPTEURS

  摘要：

  本发明涉及电子不足的受体化合物，从这些电子不足的受体化合物合成的给体-受体聚合物，从这些给体-受体聚合物合成的半导体器件，以及这些电子不足的受体化合物、给体-受体聚合物和半导体器件的合成方法。

  公开号：

  WO2016010485A1
• 作为产物：
  描述：

  2-呋喃羧酰胺 在 N-溴代丁二酰亚胺(NBS) 、 亚硝酸异戊酯 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,6-bis(5-bromofuran-2-yl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Synthesis of Ultrahighly Electron-Deficient Pyrrolo[3,4-d]pyridazine-5,7-dione by Inverse Electron Demand Diels–Alder Reaction and Its Application as Electrochromic Materials

  摘要：

  A new electron acceptor 6-alkylpyrrolo[3,4-d]pyridazine-5,7-dione (PPD) with a very low LUMO level has been synthesized via a challenging inverse electron demand DielsAlder reaction between thiophene and furan-decorated tetrazine substrates and an electron-deficient 1-alkyl-1H-pyrrole-2,5-dione unit. The PPD monomer has been incorporated into a series of donoracceptor-type conjugated polymers as electrochromic materials with good optical contrast, fast switching speed, and high coloration efficiency.

  DOI：

  10.1021/ol503178m

文献信息

• Click‐Functionalization of a Poly(Tetrazine‐co‐Fluorene)‐Conjugated Polymer with a Series of <i>trans</i> ‐Cyclooctene Derivatives
  作者：Vladimir Kardelis、Maria M. Denk、Alex Adronov

  DOI：10.1002/anie.202010795

  日期：2021.2.8

  polycondensation of 3,6‐bis(5‐bromofuran‐2‐yl)‐1,2,4,5‐tetrazine and a fluorene diboronate derivative. It can undergo efficient and quantitative post‐polymerization inverse‐electron‐demand Diels–Alder click reactions with a variety of trans‐cyclooctene (TCO) derivatives. The resulting polymers were oxidized to convert dihydropyridazine rings into pyridazines. The absorption spectra of the product polymers

  通过3,6-双（5-溴呋喃-2-基）-1,2,4,5-四嗪和芴二硼酸酯衍生物的Suzuki缩聚反应制得可溶的聚（四嗪）聚合物。它可以通过各种反式反应进行高效且定量的聚合后逆电子需求Diels-Alder点击反应环辛烯（TCO）衍生物。氧化所得聚合物以将二氢哒嗪环转化为哒嗪。在氧化之前和之后，产物聚合物的吸收光谱显示出与附接的侧链的空间位阻相关的七色位移。相对于原始的聚四嗪，它们还表现出显着增强的荧光强度。凝胶渗透色谱法表明产物聚合物表现出更长的保留时间，而NMR端基分析表明聚合物保持相对恒定的聚合度。通过与TCO官能化的聚（乙二醇）链反应可轻松制备接枝共聚物，并使聚（四嗪）与bis-TCO交联剂反应可制得交联泡沫。
• Novel synthesis of unsymmetrically substituted<i>s</i>-tetrazines
  作者：S. A. Lang、B. D. Johnson、E. Cohen

  DOI：10.1002/jhet.5570120612

  日期：1975.12

  AbstractThe synthesis of unsymmetrical 3‐aryl and 3‐heterocyclic s‐tetrazines has been examined and the scope of the reaction and the product distribution is discussed. The products included unsymmetrical and symmetrical s‐tetrazines, hydrazines, diimides, tetrazoles and triazoles with the composition of the mixtures with respect to structural type varying with the individual reactions. Some transformations with the system are discussed.
• DONOR-ACCEPTOR POLYMERS
  申请人：AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH

  公开号：US20170174826A1

  公开（公告）日：2017-06-22

  The present invention relates to compounds that are electron-deficient acceptors, donor-acceptor polymers that are synthesized from such electron-deficient acceptors, semiconductor devices synthesized from such donor-acceptor polymers and methods of synthesis of such electron-deficient acceptors, donor-acceptor polymers and semiconductor devices.
• Synthesis of Ultrahighly Electron-Deficient Pyrrolo[3,4-<i>d</i>]pyridazine-5,7-dione by Inverse Electron Demand Diels–Alder Reaction and Its Application as Electrochromic Materials
  作者：Qun Ye、Wei Teng Neo、Ching Mui Cho、Shuo Wang Yang、Tingting Lin、Hui Zhou、Hong Yan、Xuehong Lu、Chunyan Chi、Jianwei Xu

  DOI：10.1021/ol503178m

  日期：2014.12.19

  A new electron acceptor 6-alkylpyrrolo[3,4-d]pyridazine-5,7-dione (PPD) with a very low LUMO level has been synthesized via a challenging inverse electron demand DielsAlder reaction between thiophene and furan-decorated tetrazine substrates and an electron-deficient 1-alkyl-1H-pyrrole-2,5-dione unit. The PPD monomer has been incorporated into a series of donoracceptor-type conjugated polymers as electrochromic materials with good optical contrast, fast switching speed, and high coloration efficiency.
• [EN] DONOR-ACCEPTOR POLYMERS<br/>[FR] POLYMÈRES DONNEURS-ACCEPTEURS
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2016010485A1

  公开（公告）日：2016-01-21

  The present invention relates to compounds that are electron-deficient acceptors, donor- acceptor polymers that are synthesized from such electron-deficient acceptors, semiconductor devices synthesized from such donor-acceptor polymers and methods of synthesis of such electron-deficient acceptors, donor-acceptor polymers and semiconductor devices.

  本发明涉及电子不足的受体化合物，从这些电子不足的受体化合物合成的给体-受体聚合物，从这些给体-受体聚合物合成的半导体器件，以及这些电子不足的受体化合物、给体-受体聚合物和半导体器件的合成方法。