(2-ferrocenyl)indene | 140175-35-5

• 英文名称: (2-ferrocenyl)indene
• 英文别名: (2-indenyl)ferrocene；2-ferrocenylindene；2-indenylferrocene
• CAS: 140175-35-5
• 化学式: C₁₉H₁₆Fe
• 分子量: 300.183
• InChiKey: XOCWZFAXFXMCAY-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：

  (2-ferrocenyl)indene 、 六羰基铬 在 CH₃CN 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以60%的产率得到[η6-(2-ferrocenyl)-indene]-Cr(CO)3
  参考文献：
  名称：

  Designing Molecules for Metal−Metal Electronic Communication:  Synthesis and Molecular Structure of the Couple of Heterobimetallic Isomers [η⁶-(2-Ferrocenyl)indene]-Cr(CO)₃ and [η⁶-(3-Ferrocenyl)indene]-Cr(CO)₃

  摘要：

  The heterobinuclear isomers [eta(6)-(2-ferrocenybindene]-Cr(CO)(3) (1) and [eta(6)-(3-/errocenyl)indene]-Cr(CO)(3) (2) have been prepared and the crystal structure determination showed that the Fe(C5H5) and Cr(CO)(3) groups in the two molecules are disposed in different conformations with respect to the Cp-indene bridging ligand, cisoid in 1 and transoid in 2. Preliminary electrochemical (CV) and spectroscopic (IR and near-IR) results obtained for the corresponding monooxidized 1(+) and 2(+) demonstrate the existence of stronger electronic coupling in 1(+) than in 2(+).

  DOI：

  10.1021/om050307c
• 作为产物：
  描述：

  methyl ferrocenecarboxylate 、 Grignard reagent of o-xylylene dichloride 以 四氢呋喃 为溶剂， 以68%的产率得到(2-ferrocenyl)indene
  参考文献：
  名称：

  含官能团的未桥联双（2-R-茚基）锆茂烃的合成及丙烯聚合反应的研究

  摘要：

  合成并表征了五个具有2-烷基和2-芳基取代基的新的茚基锆茂金属。为了合成配体，研究了二格氏试剂1，2-双（镁甲基）苯二氯作为2-取代的茚的合成子。该方法提供了对多种官能化的2-茚基茂金属的访问，例如双（2-二茂铁基茚）二氯化锆和双（2-金刚烷基茚基）二氯化锆。双[2-（4-（二甲基氨基）苯基）茚基]二氯化锆的晶体学表征显示一种抗固态具有二甲基氨基取代基与芳基环的共面取向的构象。在不同温度下，在存在MAO的条件下，研究了五种二氧化锆在液态丙烯中的聚合行为，并将结果与​​已知的催化剂体系双（2-苯基茚基）二氯化锆/ MAO（M1 / MAO）进行了比较。在丙烯聚合中2-芳基茚金属茂的生产率约为100-7000 kg PP /（（（Zr摩尔）h）。相反，在丙烯聚合中，（2-金刚烷烯基）金属茂表现出非常低的生产率，为6kg PP /（（Zr的摩尔）h）。

  DOI：

  10.1021/om990083w

文献信息

• Synthesis of (ferrocenyl-indenyl)cyclopentadienyliron compounds with and without a bridging group via a CpFe transfer reaction
  作者：Song-Gil Lee、Su Seong Lee、Young Keun Chung

  DOI：10.1016/s0020-1693(98)00368-5

  日期：1999.3

  A series of ferrocenyl-indenyl}cyclopentadienyliron complexes with and without a spacer (spacer = -C6H4-, -C=C-, -CH2-) was prepared using a CpFe transfer reaction. All the compounds studied showed two successive one-electron transfers. The Delta E-1/2 values depend upon the spacer in the order: acetylenic > methylene > phenylene. The complex 1-(C5H5FeC5H4)-indenyl} FeCp (1b) was characterized by X-ray diffraction. (C) 1999 Elsevier Science S.A. All rights reserved.
• Charge Transfer through Isomeric Unsaturated Hydrocarbons. Redox Switchable Optical Properties and Electronic Structure of Substituted Indenes with a Pendant Ferrocenyl
  作者：Saverio Santi、Laura Orian、Alessandro Donoli、Christian Durante、Annalisa Bisello、Paolo Ganis、Alberto Ceccon、Laura Crociani、Franco Benetollo

  DOI：10.1021/om700673m

  日期：2007.11.1

  A family of (ferrocenyl)indenes, (2-ferrocenyl)indene, (2-ferrocenyl)tetramethylindene, (2-ferrocenyl)hexamethylindene, (3-ferrocenyl)indene, and (3-ferrocenyl)hexamethylindene, and the corresponding monooxidized cations have been prepared. The results of a structural and spectroelectrochemical study are discussed. The availability of pairs of isomers with known geometries and differently methylated indenes allowed the detailed investigation of how slight geometric and electronic modifications affect their physical properties. The molecular structures have been determined by X-ray diffraction and compared with the fully optimized structures calculated with state-of-the-art DFT methods. Calculated and crystallographic structures agree in establishing the dependence of the orientation of the indene moiety and the ferrocenyl cyclopentadienyl rings on the degree of methylation. The UV-vis spectra and in particular the appearance upon oxidation of a new near-IR absorption, whose energy and intensity increase with the degree of methylation and cyclopentadienyl-indene planarity, are rationalized in the framework of the Hush theory and at quantum chemistry level by DFT and TD-DFT calculations.
• Synthesis and structure of mono(cyclopentadienyl)- and bis(cyclopentadienyl)-substituted ferrocenes
  作者：Herbert Plenio

  DOI：10.1021/om00041a019

  日期：1992.5

  The reactions of the cyclopentenones 3,4-dimethylcyclopentenone, 1-indanone, and 2-indanone with mono- and dilithioferrocene lead to the synthesis of cyclopentadienyl-substituted ferrocenes: (3,4-dimethyl-cyclopenta-1,3-dienyl)ferrocene (1), (1-indenyl)ferrocene (3), (2-indenyl)ferrocene (4), and 1,1'-bis(3,4-dimethylcyclopenta-1,3-dienyl)ferrocene (2). The crystal structure of compound 2 was determined. The crystal data are as follows: C24H26Fe, triclinic, P1BAR, a = 7.561 (2) angstrom, b = 10.738 (2) angstrom, c = 13.005 (3) angstrom = 102.05 (3)-degrees, beta = 104.29 (3)-degrees, gamma- 108.84 (3)-degrees, V = 919.1 (4) angstrom3, Z = 2, R = 0.0279, and R(W) = 0.0398 on the basis of 2336 reflections with F greater-than-or-equal-to 4-sigma-(F). It displays an unusual cofacial arrangement of the two 3,4-dimethylcyclopenta-1, 3-dienyl rings. The lithium salt of 1 reacts with FeCl2 to give the triferrocenyl bis(1-ferrocenyl-3,4-dimethylcyclopentadienyl)ferrocene (5). The reaction of the dilithium salt of 2 with FeCl2 yields a mixture of polymeric ferrocenes.
• Mixed Valence Properties in Ferrocenyl-Based Bimetallic FeCp−Indenyl−ML_<i>n</i> Complexes: Effect of the ML_<i>n</i> Group
  作者：Saverio Santi、Christian Durante、Alessandro Donoli、Annalisa Bisello、Laura Orian、Alberto Ceccon、Laura Crociani、Franco Benetollo

  DOI：10.1021/om800954b

  日期：2009.6.22

  A series of ferrocenyl-based complexes of general structure [eta(5)-(2-ferrocenyl)indenyI]MLn [MLn = RuCp*, FeCp, IrCOD, Mn(CO)(3), and Cr(CO)(2)NO] were synthesized with the aim of tuning the effect of the nature of the second metal group MLn on the magnitude of the metal-metal electronic coupling in their mixed valence ions generated by electrochemical oxidation. The electronic interaction was probed by determining different and independent physical properties, the potential splitting in the cyclic voltammograms, and the IT bands in the near-IR spectra, which were rationalized in the framework of Marcus-Hush theory and at the quantum chemistry level by the density functional theory and TD density functional theory methods. On the basis of the obtained results, we were able to establish a trend based on the magnitude of the Fe-M electron transfer parameters H-ab and alpha ranging from weakly to moderately coupled mixed valence ions.