1,4-bis(ferrocenylethynyl)benzene | 185225-31-4

• 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: 1,4-bis(ferrocenylethynyl)benzene
• 英文别名: 1,4-Bis(ferrocenylethynyl)-benzene；1,4-bis(2-cyclopenta-1,3-dien-1-ylethynyl)benzene;cyclopenta-1,3-diene;iron(2+)
• CAS: 185225-31-4
• 化学式: C₃₀H₂₂Fe₂
• 分子量: 494.199
• InChiKey: QQZLQPZGQLZEDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  decaborane 、 1,4-bis(ferrocenylethynyl)benzene 在 乙硫醚 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以42%的产率得到1,4-bis(2-ferrocenyl-o-carboran-1-yl)benzene
  参考文献：
  名称：

  碳硼烷桥接的二茂铁基共轭分子：合成，结构，电化学和光物理性质

  摘要：

  炔基桥联的双二茂铁基衍生物与十硼烷之间的反应产生新的对称的二茂铁基取代的碳硼烷8-11。所有新化合物均已通过NMR和HRMS进行了鉴定和充分表征。目标化合物8-11的分子结构通过单晶X射线分析确定。报道了二茂铁基取代的碳硼烷的电化学研究，结果表明，在这些对称的共轭低聚物中，两个二茂铁基之间存在大量电子通讯。混合价物质的热力学稳定性以11 < 8 < 10 < 9的顺序增加。

  DOI：

  10.1039/d0nj00826e
• 作为产物：
  描述：

  iodoferrocene 、 1,4-二乙炔基苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper diacetate 、 二异丙胺 作用下， 以 further solvent(s) 为溶剂， 以96%的产率得到1,4-bis(ferrocenylethynyl)benzene
  参考文献：
  名称：

  Ruthenium or Ferrocenyl Homobimetallic and RuPdRu and FePdFe Heterotrimetallic Complexes Connected by Unsaturated, Carbon-Rich −C⋮CC₆H₄C⋮C− Bridges

  摘要：

  The reaction of 1,4-diethynylbenzene with cis-RuCl2(dppe)(2) and iodoferrocene gave the homobimetallic systems Cl(dppe)(2)Ru-C=CC6H4C=C-Ru(dppe)(2)Cl (2) and (eta 5-C5H5)Fe(eta(5)-C5H4)-C=CC6H4C= C-(eta(5)-C5H4)Fe(eta(5)-C5H5) (3), respectively. The organometallic terminal alkynes Cl(dppe)(2)Ru-C=CC6H4C=CH (6) and (eta(5)-C5H5)Fe(eta(5)-C5H4-C=CC6H4C=CH) (8), obtained by desilylation of the corresponding complexes Cl(dppe)(2)Ru-C=CC6H4C=(CSiPr3)-Pr-i (5) and (eta(5)-C5H5)Fe(eta(5)-C5H4-C=CC6H4C=(CSiPr3)-Pr-i) (7), were used as key starting products for access to the heterotrimetallic systems trans-(P(n)Bu(3))(2)Pd[-C=CC6H4C=C-Ru(dppe)(2)-Cl](2) (10; 53%) and trans-(PnBu(3))(2)Pd[(-C=CC6H4C-C5H4-eta(5))Fe(eta(5)-C5H5)](2). (11; 73%) by reaction with PdCl2(PBu(3))(2). The cyclic voltammetry studies of the complexes 2 and 3 have shown that the electrochemical response was strongly dependent on the connection type between the two terminal organometallic fragments and the organic bridge and that the insertion of the palladium moiety trans-Pd(PBu(3))(2) in the trimetallic complexes 10 and 11 induced totally different electrochemical behavior.

  DOI：

  10.1021/om960664a

文献信息

• Synthesis of a diferrocenylvinylidene complex by migration of a ferrocenyl substituent
  作者：Marcus Korb、Stephen A. Moggach、Paul J. Low

  DOI：10.1039/d1cc00605c

  日期：——

  2-ferrocenyl migration has been observed following reactions of [Ru(dppe)Cp][BArF4] with diferrocenylacetylene, extending the scope of group rearrangments beyond methyl (Wagner–Meerwein) and phenyl entities. Ferrocene-containing bis(alkynes) RCCArCCR (R = Fc, Ar = 1,4-phenylene; R = Ph, Ar = 1,1′-ferrocenylene) gave bimetallic bis(vinylidene) complexes following two consecutive rearrangements.

  [Ru（dppe）Cp] [BAr F 4 ]与二铁茂铁乙炔反应后，观察到不寻常的1,2-二茂铁基迁移，将基团重排的范围扩展到了甲基（Wagner-Meerwein）和苯基实体之外。含二茂铁的双（炔）RC CArC CR（R = Fc，Ar = 1,4-亚苯基; R = Ph，Ar = 1,1'-二茂铁基）经过两次连续重排后得到双金属双（亚乙烯基）配合物。
• Asymmetrie Ethynes. Syntheses of Ethynylferrocene Paradigms
  作者：Johann Polin、Herwig Schottenberger、Karl Eberhard Schwarzhans

  DOI：10.1515/znb-1996-1204

  日期：1996.12.1

  additions have been evaluated in the preparation of substituted ferrocenylethynes with intended use of these materials in electrochemical and nonlinear optical investigations. Asymmetric ferrocenylethynes are promising candidates for applications in contemporary materials science. Synthetically, 1,4-bis(ferrocenylethynylene)benzene (1), 1,3,5-tris(ferrocenylethynylene) benzene (2), and 9 ,10-bis(ferroceny

  已经研究了双功能乙炔的合成方法。直接乙炔化、Stephens-Castro 反应、Pd 催化的 Hagihara 偶联、金属转移反应和亲核加成已在取代二茂铁的制备中进行了评估，这些材料预期用于电化学和非线性光学研究。不对称二茂铁乙炔是当代材料科学应用的有希望的候选者。合成上，1,4-双(二茂铁基乙炔)苯(1)、1,3,5-三(二茂铁基乙炔)苯(2)和9,10-双(二茂铁基乙炔)蒽(3)以高产率获得，而4-二茂铁基乙炔-2,3,5,6-四氟苯乙烯 (4) 和 (二茂铁基乙炔基) 三苯基硼酸钾 (5) 只能以中等产率获得。
• Synthesis, Properties, and Redox Behavior of 1,1,4,4-Tetracyano-2-ferrocenyl-1,3-butadienes Connected by Aryl, Biaryl, and Teraryl Spacers
  作者：Taku Shoji、Akifumi Maruyama、Chisa Yaku、Natsumi Kamata、Shunji Ito、Tetsuo Okujima、Kozo Toyota

  DOI：10.1002/chem.201405004

  日期：2015.1.2

  Aryl‐substituted 1,1,4,4‐tetracyano‐1,3‐butadienes (FcTCBDs) and bis(1,1,4,4‐tetracyanobutadiene)s (bis‐FcTCBDs), possessing a ferrocenyl group on each terminal, were prepared by the reaction of a variety of alkynes with tetracyanoethylene (TCNE) in a [2+2] cycloaddition reaction, followed by retro‐electrocyclization of the initially formed [2+2] cycloadducts (i.e., cyclobutene derivatives). The characteristic

  芳基取代的1,1,4,4-四氰基-1,3-丁二烯（FcTCBDs）和双（1,1,4,4-四氰基丁二烯）（bis-FcTCBDs）在每个末端均具有二茂铁基。通过在[2 + 2]环加成反应中各种炔烃与四氰基乙烯（TCNE）的反应制备，然后对最初形成的[2 + 2]环加合物（即环丁烯衍生物）进行逆电环化。通过使用紫外/可见光谱研究了供体（二茂铁）和受体（TCBD）部分之间的特征分子内电荷转移（ICT）。通过循环伏安法（CV）和微分脉冲伏安法（DPV）检查了FcTCBD和bis-FcTCBD的氧化还原行为，这揭示了它们根据二茂铁和TCBD部分的数量进行多电子转移的特性。而且，
• Polymeric and carbon compositions with metal nanoparticles
  申请人：——

  公开号：US20030114698A1

  公开（公告）日：2003-06-19

  The invention comprises a chemical composition with the structure shown below. The composition can be polymerized or pyrolyzed, forming transition metal nanoparticles homogeneously dispersed in a thermoset or carbon composition. The size of the nanoparticles can be controlled by manipulating the number and arrangement of functional groups in the composition and by changing the conditions of the polymerization or pyrolysis. The resulting thermosets and carbon compositions have useful magnetic, electric, mechanical, catalytic and/or optical properties. 1 wherein A is selected from the group consisting of H, 2 wherein M is a metal selected independently from the group consisting of Fe, Mn, Ru, Co, Ni, Cr and V; wherein Rx is independently selected from the group consisting of an aromatic, a substituted aromatic group and combinations thereof; wherein Ry is independently selected from the group consisting of an aromatic, a substituted aromatic group and combinations thereof; wherein m is ≧ 0; wherein s is ≧ 0; wherein z is ≧ 0; and wherein m and s are independently determined in each repeating unit.

  该发明涉及一种化学组合物，其结构如下所示。该组合物可以聚合或热解，形成过渡金属纳米颗粒均匀分散在热固性或碳组合物中。纳米颗粒的大小可以通过操纵组合物中的功能基团数量和排列方式以及改变聚合或热解条件来控制。由此产生的热固性和碳组合物具有有用的磁性、电性、机械性、催化性和/或光学性能。其中A选自H组，M是独立选择的金属，包括Fe、Mn、Ru、Co、Ni、Cr和V；Rx和Ry分别独立选择芳香族、取代芳香族基团和它们的组合；m、s和z分别为大于等于0的数；m和s在每个重复单元中独立确定。