(4-ethynylphenyl)ethynylferrocene | 169231-37-2

• 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: (4-ethynylphenyl)ethynylferrocene
• 英文别名: 1-(ferrocenylethynyl)-4-(ethynyl)benzene；4-(Ferrocenylethynyl)phenylacetylene；cyclopenta-1,3-diene;1-(2-cyclopenta-2,4-dien-1-ylethynyl)-4-ethynylbenzene;iron(2+)
• CAS: 169231-37-2
• 化学式: C₂₀H₁₄Fe
• 分子量: 310.178
• InChiKey: NFIIJDFRHHNEAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (4-ethynylphenyl)ethynylferrocene 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以22%的产率得到
  参考文献：
  名称：

  二茂铁基封端的分子棒：合成，结构和性能†

  摘要：

  设计了一系列二茂铁基苯基乙炔基棒1-11，并通过Pd催化的Sonogashira交叉偶联和氧化均相偶联反应合成。杆1-11中的二茂铁基部分连接在苯乙炔基单元的对位/间位或炔属单元上。探索了增强共轭和连接性（meta / para）对光子和电化学性质的影响。对位键和丁二炔键降低了杆中的带隙。所述间位连接的二茂铁基苯基乙炔基杆2，4，和10相比显示出良好的HOMO-LUMO分离对连接杆1，3，9。杆的单晶X射线结构2，4，10，14和19中报告。在棒的二茂铁单元2，4，和10处于反式构型相对于该苯环。

  DOI：

  10.1039/c3nj01244a
• 作为产物：
  描述：

  (η(5)-C5H5)Fe(η(5)-C5H4-CCC6H4CCSi(i)Pr) 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(4-ethynylphenyl)ethynylferrocene
  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

• 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。
• Intermetallic Communication through Carbon Wires in Heterobinuclear Cationic Allenylidene Complexes of Chromium
  作者：Normen Szesni、Matthias Drexler、Jörg Maurer、Rainer F. Winter、Frédéric de Montigny、Claude Lapinte、Stefan Steffens、Jürgen Heck、Bernhard Weibert、Helmut Fischer

  DOI：10.1021/om0607301

  日期：2006.11.1

  CuI-catalyzed coupling of 15a with M}−Br (M} = Ru(CO)2Cp, Fe(CO)2Cp*) affords the binuclear complexes The symmetrical binuclear complex is formed by oxidative coupling of 15a with [Cu(OAc)2]. The attachment of a ferrocenyl group to the chromium center via PPh2 to give is achieved via displacement of a cis-CO ligand in by PPh2Fc. On addition of Co2(CO)8 to a Co2(CO)6 unit adds to the C⋮C bond to form a trinuclear

  [（CO）5 M（THF）]（M = Cr，W）与锂化的2-乙炔基喹啉反应，然后用[R 3 O] BF 4（R = Me，Et）将所得炔基五羰基金属化物烷基化，得到烯基亚烷基络合物其中亚烯基链的末端碳原子是N-烷基化喹啉环的一部分。[（CO）5 M（THF）]（M = Cr，W）与锂化的2-乙炔基吡啶衍生物，Li [C⋮CC 5 H 4 BrN]和[Et 3 O] BF 4的反应得到烯基亚烷基络合物含有在5或6位溴化的末端六元N杂环。各种炔基可以通过[PdCl 2 ]引入环的5-位（PPH 3）2 ]催化的5-溴-取代的allenylidene复合物与末端炔烃HC⋮CR '（R'= TMS中，Ph，C耦合10 ħ 21，4-C 6 H ^ 4 -C⋮器CPh， 4-C 6 H 4 -C⋮CH，Fc（Fc =（C 5 H 4）FeCP），4-C 6 H 4 -C⋮CFc，4-C 6 H 4 -C⋮CC
• Donor–acceptor meso-alkynylated ferrocenyl BODIPYs: synthesis, structure, and properties
  作者：Rajneesh Misra、Bhausaheb Dhokale、Thaksen Jadhav、Shaikh M. Mobin

  DOI：10.1039/c3dt51374b

  日期：——

  meso-Alkynylated ferrocenyl BODIPYs (3–6) with varying conjugation length have been designed, and synthesized using the palladium catalyzed Sonogashira cross-coupling reaction of meso-chloro BODIPY with the corresponding ferrocenylethynes. These BODIPYs have been designed to improve the electronic communication between the donor ferrocene, and the acceptor BODIPY. The photonic and electrochemical properties indicate charge transfer (CT) from the ferrocene to the BODIPY. Single crystal X-ray structures of 2′, 3, and 6 show interesting supramolecular interactions. Computational studies were used to study the electronic structure of the BODIPYs.

  设计并合成了不同共轭长度的meso-炔基铁烯基BODIPYs（3–6），采用了钯催化的Sonogashira交叉偶联反应，将meso-氯BODIPY与相应的铁烯炔结合。这些BODIPYs旨在改善供体铁烯与受体BODIPY之间的电子传递。光电和电化学性质表明存在从铁烯到BODIPY的电荷转移（CT）。2′、3和6的单晶X射线结构显示出有趣的超分子相互作用。计算研究用于分析BODIPYs的电子结构。
• Electrochemical control of a non-covalent binding between ferrocene and beta-cyclodextrin
  作者：V. Kolivoška、M. Mohos、I. V. Pobelov、S. Rohrbach、K. Yoshida、W. J. Hong、Y. C. Fu、P. Moreno-García、G. Mészáros、P. Broekmann、M. Hromadová、R. Sokolová、M. Valášek、Th. Wandlowski

  DOI：10.1039/c4cc04102j

  日期：——

  The forces required for the detachment of ferrocene (Fc) from β-cyclodextrin (βCD) in a single host (βCD)–guest (Fc) complex were investigated using force spectroscopy under electrochemical conditions. The redox state of the guest Fc moiety as well as the structure of the supporting matrix was found to decisively affect the nanomechanical properties of the complex.

  在电化学条件下，通过力谱学研究了单个主客体（β-环糊精（βCD）–二茂铁（Fc））复合物中从β-环糊精（βCD）上分离二茂铁（Fc）所需的力。结果发现，客体Fc部分的氧化还原状态以及支撑基质的结构对复合物的纳米机械性能有决定性影响。