4-bromo-7-ferrocenylethynylbenzo[1,2,5]thiadiazole | 1417365-37-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4-bromo-7-ferrocenylethynylbenzo[1,2,5]thiadiazole
• 英文别名: FcCC(benzo-2,1,3-thiadiazole-4,7-diyl)CCFc；cyclopenta-1,3-diene;4-(2-cyclopenta-1,3-dien-1-ylethynyl)-7-(2-cyclopenta-2,4-dien-1-ylethynyl)-2,1,3-benzothiadiazole;iron(2+)
• CAS: 1417365-37-7
• 化学式: C₃₀H₂₀Fe₂N₂S
• 分子量: 552.262
• InChiKey: BVGVSVSMXCIXEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-bromo-7-ferrocenylethynylbenzo[1,2,5]thiadiazole 以 1,2-二氯乙烷 为溶剂， 生成 FcCC(benzo-2,1,3-thiadiazole-4,7-diyl)CCFc(1+)
  参考文献：
  名称：

  Long-Range Intramolecular Electronic Communication in Bis(ferrocenylethynyl) Complexes Incorporating Conjugated Heterocyclic Spacers: Synthesis, Crystallography, and Electrochemistry

  摘要：

  A new series of bis(ferrocenylethynyl) complexes, 3-7, and a mono(ferrocenylethynyl) complex, 8, have been synthesized incorporating conjugated heterocyclic spacer groups, with the ethynyl group facilitating an effective long-range intramolecular interaction. The complexes were characterized by NMR, IR, and UV-vis spectroscopy as well as X-ray crystallography. The redox properties of these complexes were investigated using cyclic voltamrnetry and spectroelectrochemistry. Although there is a large separation of,similar to 14 angstrom between the two redox centers, Delta E-1/2 values in this series of complexes ranged from 50 to 110 mV. The appearance of intervalance charge-transfer bands in the UV-vis-near-IR region for the monocationic complexes further confirmed effective intramolecular electronic communication. Computational studies are presented that show the degree of delocalization across the Fc-C C-C C-Fc (Fc = C5H5FeC5H4) highest occupied molecular orbital.

  DOI：

  10.1021/ic3024887
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 二茂铁乙炔 在 copper(l) iodide 、 palladium diacetate 、 二异丙胺 、 三苯基膦 作用下， 反应 24.0h， 以82%的产率得到4-bromo-7-ferrocenylethynylbenzo[1,2,5]thiadiazole
  参考文献：
  名称：

  Long-Range Intramolecular Electronic Communication in Bis(ferrocenylethynyl) Complexes Incorporating Conjugated Heterocyclic Spacers: Synthesis, Crystallography, and Electrochemistry

  摘要：

  A new series of bis(ferrocenylethynyl) complexes, 3-7, and a mono(ferrocenylethynyl) complex, 8, have been synthesized incorporating conjugated heterocyclic spacer groups, with the ethynyl group facilitating an effective long-range intramolecular interaction. The complexes were characterized by NMR, IR, and UV-vis spectroscopy as well as X-ray crystallography. The redox properties of these complexes were investigated using cyclic voltamrnetry and spectroelectrochemistry. Although there is a large separation of,similar to 14 angstrom between the two redox centers, Delta E-1/2 values in this series of complexes ranged from 50 to 110 mV. The appearance of intervalance charge-transfer bands in the UV-vis-near-IR region for the monocationic complexes further confirmed effective intramolecular electronic communication. Computational studies are presented that show the degree of delocalization across the Fc-C C-C C-Fc (Fc = C5H5FeC5H4) highest occupied molecular orbital.

  DOI：

  10.1021/ic3024887

文献信息

• Donor–Acceptor Ferrocenyl-Substituted Benzothiadiazoles: Synthesis, Structure, and Properties
  作者：Rajneesh Misra、Prabhat Gautam、Thaksen Jadhav、Shaikh M. Mobin

  DOI：10.1021/jo4005734

  日期：2013.5.17

  This article reports the design, and synthesis of D−π1–A−π2–D unsymmetrical, and D−π1–A−π2–A−π1–D symmetrical type of ferrocenyl-substituted benzothiadiazoles by the Pd-catalyzed Sonogashira, and Stille coupling reactions. The photophysical and electrochemical behavior of the ferrocenyl-substituted benzothiadiazoles show strong donor–acceptor interaction. The increase in the number of acceptor benzothiadiazole

  本文报告的设计，以及d-π的合成1 -A-π 2 -D不对称，和d-π 1 -A-π 2 -A-π 1 -D对称型由Pd的二茂铁基-取代的benzothiadiazoles的催化的Sonogashira和Stille偶联反应。二茂铁基取代的苯并噻二唑的光物理和电化学行为显示出强的供体-受体相互作用。受体苯并噻二唑单元数量的增加导致能隙的降低，这导致吸收光谱的红移。3a，5a和5g的单晶X射线结构 获得显示出有趣的超分子相互作用的化合物。
• Aryl-Substituted Unsymmetrical Benzothiadiazoles: Synthesis, Structure, and Properties
  作者：Rajneesh Misra、Prabhat Gautam、Shaikh M. Mobin

  DOI：10.1021/jo402111q

  日期：2013.12.20

  A family of unsymmetrical donor–acceptor, ferrocenyl-substituted benzothiadiazoles of types D1–π–A−π–D2, D1–π–A1–π–A2, D1–A−π–D2, and D1–A1–A2–D2, bearing a variety of electron-donating and electron-withdrawing groups, were designed and synthesized. Their photophysical, electrochemical, and computational properties were explored, which show strong donor–acceptor interaction. The presence of electron-rich

  D 1 –π–A–π–D 2，D 1 –π–A 1 –π–A 2，D 1 –A–π–D 2和D 1的不对称供体-受体，二茂铁基取代的苯并噻二唑家族。设计并合成了带有各种给电子基团和吸电子基团的D 1 -A 1 -A 2 -D 2。探索了它们的光物理，电化学和计算性质，显示出强的供体-受体相互作用。富电子单元蒽（6f）和三苯胺（6h）的存在），而缺电子单元1,1,4,4-四氰基-1,3-二烯（TCBD）（9b）导致带隙降低，这导致这些苯并噻二唑的吸收光谱发生红移系统。报道了6c，6g，7a和7b的单晶结构，显示出奇妙的超分子相互作用。
• Tetracyanobutadiene (TCBD) functionalized benzothiadiazole derivatives: effect of donor strength on the [2+2] cycloaddition–retroelectrocyclization reaction
  作者：Yogajivan Rout、Shaikh M. Mobin、Rajneesh Misra

  DOI：10.1039/c9nj01887e

  日期：——

  In order to explore the selectivity of the [2+2] cycloaddition–retroelectrocyclization reaction in the presence of different donor groups, a series of unsymmetrical and symmetrical mono/di 1,1,4,4-tetracyanobutadiene (TCBD) substituted benzothiadiazoles (BTDs) 2a–2g were synthesized. 2a–2e exhibit monosubstitution, whereas 2f and 2g show disubstitution of TCBD in the presence of an excess amount of

  为了探索在不同供体基团存在下[2 + 2]环加成-逆电环化反应的选择性，一系列不对称和对称的单/二1,1,4,4-四氰基丁二烯（TCBD）取代的苯并噻二唑（BTDs） ）合成了2a–2g。2a–2e显示单取代，而2f和2g显示在存在过量的四氰基乙烯（TCNE）的情况下TCBD的分解。系统地研究了BTD 2a–2g的光物理，电化学和热性质。BTD 2a–2g的吸收光谱在电磁波谱的可见光区域具有很强的电子吸收带，这对应于分子内电荷转移（ICT）。TGA数据显示，与其他BTD相比，BTD 2e具有更好的热稳定性。BTDS的电化学研究2A-2G显示在强电子通信2F和2克由于额外TCBD受体的结合。计算研究表明，加入一个额外的TCBD单元和末端供体基团的系统变化是调节HOMO-LUMO能级的关键因素。通过单晶X射线衍射分析确认了BTD 2c的结构。