1,1'-bis(trimethylsilylethynyl)biferrocene | 171359-48-1

• 分子结构分类: 有机化合物 - 有机金属化合物
• 英文名称: 1,1'-bis(trimethylsilylethynyl)biferrocene
• 英文别名: 1',6'-bis(trimethylsilylethynyl)biferrocene；[(C5H4)Fe(C5H4C*CSi(CH3)3)]2；[Me3SiCC(ferrocenyl)2CCSiMe3]；[(CH3)3SiC2(fc)2C2Si(CH3)3]；[(CH3)3SiC2(ferrocenyl)2C2Si(CH3)3]；1-cyclopenta-1,3-dien-1-ylcyclopenta-1,3-diene;2-cyclopenta-2,4-dien-1-ylethynyl(trimethyl)silane;iron(2+)
• CAS: 171359-48-1
• 化学式: C₃₀H₃₄Fe₂Si₂
• 分子量: 562.465
• InChiKey: UXOCOMSKJTVQDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1,1'-bis(trimethylsilylethynyl)biferrocene 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以72 %的产率得到1',1'''-bis(ethynyl)biferrocene
  参考文献：
  名称：

  A convenient synthesis of ferrocene-(ethynylphenyl)thioacetates

  摘要：

  保护基策略可用于合成对称、不对称和多二茂铁基分子线，并以硫代乙酸酯为端基--这些稀有分子在制造分子纳米电子学方面具有巨大潜力。

  DOI：

  10.1039/d3dt02954a
• 作为产物：
  描述：

  1-trimethylsilylethynyl-1'-iodoferrocene 在 Cu 作用下， 以 neat (no solvent) 为溶剂， 以40%的产率得到1,1'-bis(trimethylsilylethynyl)biferrocene
  参考文献：
  名称：

  Toward the Development of Molecular Wires:  A Terpyridine Spacer Containing Polyferrocenylalkyne Linkages

  摘要：

  The preparation, characterizations, and electrochemical measurements of the terpyridine-ferrocenylalkyne spacers (tpy-C C-(fc)(n)-C C-tpy; tpy = terpyridyl; fc = ferrocenyl; n = 2, 3) are described. In the electrochemical measurements, the charge could be delocalized to the cyclopentadienyl and ethynyl moieties caused by the built-up charge density upon oxidation of the ferrocenyl moiety.

  DOI：

  10.1021/om051061e

文献信息

• Syntheses, structure, and electrochemical properties of homo-metallic binuclear complexes containing ferrocenyl–ethynyl spacers
  作者：Teng-Yuan Dong、Chiao-Pei Chen、Chun-Ting Kuo、Shu-Fan Lin、Chen-Ni Chen、Shao-Chun Hsu、Yuh-Sheng Wen

  DOI：10.1016/j.ica.2010.03.012

  日期：2010.5

  electrochemical properties in the series of multinuclear ferrocenyl–ethynyl complexes with formula [( η 5 -C 5 R 5 )(P 2 )M II –C C–(fc) n –C C–M II (P 2 )( η 5 -C 5 R 5 )] (fc = ferrocenyl; M = Fe(II), Ru(II), Os(II); R = H, CH 3 ; P 2 = Ph 2 PCH 2 CH 2 PPh 2 (dppe), (C 2 H 5 ) 2 PCH 2 CH 2 P(C 2 H 5 ) 2 (depe)) are reported. Complexes with more electron-rich ligand environment, such as [M( η 5 -C 5 R 5 )P

  摘要具有[[η5 -C 5 R 5）（P 2）M II -CC-（fc）n -CC-M II（P 2）（ η5 -C 5 R 5）]（fc =二茂铁基； M = Fe（II），Ru（II），Os（II）； R = H，CH 3； P 2 = Ph 2 PCH 2 CH 2 PPh 2（ dppe），（C 2 H 5）2 PCH 2 CH 2 P（C 2 H 5）2（depe））被报道。关于电子耦合的理解，还制备了具有更富电子配体环境的配合物，例如[M（η5 -C 5 R 5）P 2]（R = CH 3和P 2 = dppe，depe）。机制。结构确定证实二茂铁基团直接连接至乙炔基键，乙炔基键合至假八面体[（η5 -C 5 R 5）（P 2）M]金属中心。这些配合物经历从0.0到1的顺序可逆氧化事件。0 V称为无水CH 2 Cl 2溶液中的Ag / AgCl电极，并且低电位波已分配给两个端基
• Synthesis, Characterization, and Theoretical Studies of New Alkynylferrocene and -biferrocene Ligands and Their Platinum-Containing Dimers and Oligomers
  作者：Nicholas J. Long、Angela J. Martin、Ramon Vilar、Andrew J. P. White、David J. Williams、Muhammad Younus

  DOI：10.1021/om980986+

  日期：1999.10.1

  oligomeric platinum-containing alkynyl species (5−10). Characterization by spectroscopy and X-ray crystal structure determinations of [C5H4FeC5H4C⋮CH}2] (3), [C6H5(C2H5)3P}2PtC⋮CC5H4FeC5H4C⋮CPtP(C2H5)3}2C6H5] (5), and [(C6H5PtP(C2H5)3}2C⋮CC5H4Fe(C5H4)2FeC5H4}C⋮CPtP(C2H5)3}2C6H5)] (8) illustrates their “rigid-rod” symmetrical geometries, featuring staggered cyclopentadienyl rings and almost perfect

  一系列二取代alkynylferrocenyl和-biferrocenyl配体（的1 - 4）已被合成，并且这些然后用于形成许多二，三，和低聚含铂的炔基物种（5 - 10）。[C 5 H 4 FeC 5 H 4 C⋮CH} 2 ]（3），[C 6 H 5 （C 2 H 5）3 P} 2 PtC⋮CC的光谱学和X射线晶体结构测定5 ħ 4的FeCl 5 ħ4 C⋮CPt P（C 2 H 5）3 } 2 C 6 H 5 ]（5）和[（C 6 H 5 Pt P（C 2 H 5）3 } 2 C⋮C C 5 H 4 Fe（C 5 H 4）2 FeC 5 H 4 } C⋮CPt P（C 2 H 5）3 } 2 C 6 H 5）]（8）说明了它们的“刚性杆”对称几何形状，具有交错的环戊二烯基环和在每种情况下乙炔基键合几乎完美的反几何形状。对金属配合物的电化学和理论研究（扩展的Hückel计算
• Communication between Co₂(CO)₄dppm Units via Polyferrocenylalkyne Linkages
  作者：Leigh-Anne Hore、C. John McAdam、Joy L. Kerr、Noel W. Duffy、Brian H. Robinson、Jim Simpson

  DOI：10.1021/om000493g

  日期：2000.11.1

  The synthesis and characterization of a family of ethynylbi- and ethynylterferrocenyls, I-Fc(2)C=CR, Fc(2)C=CR, and Fc(2)(C=CR)(2) (R = Fc, SiMe3), I-Fc(3)C=CSiMe3, Fc(3)C=CSiMe3, Fc(3)(C=CSiMe3)(2), and their Co-2(CO)(6) and Co-2(CO)(4)dppm complexes are described. The structure adopted by Fc(2)[Co-2(CO)(4)dppm C2SiMe3]}(2) minimizes the steric interactions between the biferrocene and dppm moieties. Electrochemical studies show that identical redox centers-ferrocenyl termini, Co-2(CO)(4)dppm units, or ferrocenyl groups in the core-communicate independently with each other.
• Long-distance electronic interaction in a molecular wire consisting of a ferrocenyl–ethynyl unit bridging two [(η5-C5H5)(dppe)M] metal centers
  作者：Teng-Yuan Dong、Shu-Fan Lin、Chiao-Pei Chen、Shu-Wen Yeh、Hsing-Yin Chen、Yuh-Sheng Wen

  DOI：10.1016/j.jorganchem.2008.12.056

  日期：2009.4

  Several multinuclear ferrocenyl-ethynyl complexes of formula [(eta(5)-C5H5)(dppe)M-II-C C-(fc)(n)-C C-M-II(dppe)(eta(5)-C5H5)] (fc = ferrocenyl; dppe = Ph2PCH2CH2PPh2; 1: M-II = Ru2+, n = 1; 2: M-II = Ru2+, n = 2; 3: M-II = Ru2+, n = 3; 4: M-II = Fe2+, n = 2; 5: M-II = Fe2+, n = 3) were studied. Structural determinations of 2 and 4 confirm the ferrocenyl group directly linked to the ethynyl linkage which is linked to the pseudo-octahedral [(eta(5)-C5H5)(dppe)M] metal center. Complexes of 1-5 undergo sequential reversible oxidation events from 0.0 V to 1.0 V referred to the Ag/AgCl electrode in anhydrous CH2Cl2 solution and the low-potential waves have been assigned to the end-capped metallic centers. The solid-state and solution-state electronic configurations in the resulting oxidation products of [1](+) and [2](2+) were characterized by IR, X-band EPR spectroscopy, and UV-Vis at room temperature and 77 K. In [1](+) and [2](2+), broad intervalence transition band near 1600 nm is assigned to the intervalence transition involving photo-induced electron transfer between the Ru3+ and Fe2+ metal centers, indicating the existence of strong metal-to-metal interaction. Application of Hush's theoretical analysis of intervalence transition band to determine the nature and magnitude of the electronic coupling between the metal sites in complexes [1](+) and [2](2+) is also reported. Computational calculations reveal that the ferrocenyl-ethynyl-based orbitals do mix significantly with the (eta(5)-C5H5)(dppe)Ru metallic orbitals. It clearly appears from this work that the ferrocenyl-ethynyl spacers strongly contribute in propagating electron delocalization. (c) 2009 Elsevier B.V. All rights reserved.
• Synthesis, characterization and electrochemical studies of 1′,6′-bis(ethynyl)biferrocene and some metal complexes: Novel heterometallic compounds towards non-linear optics
  作者：M.C.B. Colbert、D. Hodgson、J. Lewis、P.R. Raithby、N.J. Long

  DOI：10.1016/0277-5387(95)00143-g

  日期：1995.9

  The reaction of trimethylsilylacetylene and 1',6'-diiodoferrocene (1) resulted in the formation of 1',6'-bis(trimethylsilylethynyl)biferroc (2) and, with subsequent desilylation, 1',6'-bis(ethynyl)biferrocene (3), in excellent yields. The novel difunctional ligand 3 lends itself to metal coordination, and the multimetallic complexes 1',6'-bis (manganese(I)tricarbonyl[1,2-bis(diphenylphosphino)methane]} biferrocene (4) and 1',6'-bis(rutheniumbis [1,2-bis(diphenylphosphino)methane]chloride) biferrocene (5) were formed from manganese(I)tricarbonyl[1,2-bis(diphenylphosphino)methane]bromide) and rutheniumbis[1,2-bis(diphenylphosphino)methane]dichloride}, respectively. All the compounds have been fully characterized by analytical and spectroscopic methods. Cyclic voltammetry experiments indicate that there is a large electron delocalization between the iron atoms of the biferrocene moiety and the metal centres in the one-electron-oxidized complexes. Additionally, results show that the ruthenium and manganese centres donates electron density through the acetylene linkage to the (FeCp(2))(2) ligand.