di-fluorocarbonylferrocene | 226882-94-6

• 分子结构分类: 有机化合物
• 英文名称: di-fluorocarbonylferrocene
• 英文别名: 1,1'-Bis(fluorocarbonyl)ferrocene；cyclopenta-2,4-diene-1-carbonyl fluoride;iron(2+)
• CAS: 226882-94-6
• 化学式: C₁₂H₈F₂FeO₂
• 分子量: 278.038
• InChiKey: VQSGVUCHVDFZEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三(2-氨基乙基)胺 、 di-fluorocarbonylferrocene 以 二氯甲烷 为溶剂， 以52%的产率得到N,N'-bis[[bis(aminoethyl)amino]ethyl]ferrocene-dicarboxamide
  参考文献：
  名称：

  Covalent layer-by-layer type modification of electrodes using ferrocene derivatives and crosslinkers

  摘要：

  A series of mono-substituted ferrocenes (Fecp(2)-R, R = -CONHCH2N(C2H4NH2)(2) (4), R = -CH2NHCH2N(C2H4NH2)(2) (5)) and di-substituted ferrocenes (Fe(cp-R)(2), R = -COF (3)) have been prepared, with 4 and 5 representing new compounds. The ferrocenes were grown layer-by-layer on metal oxide electrodes and crosslinked. The underlying principle of synthesis is based on repetitive and fast amide forming reactions between trimesic acid chloride (2) or Fe(cp-COF)(2) (3) and tris(2-aminoethyl)amine (6), or one of the amine-substituted ferrocenes 4 or 5 on a 3-aminopropyl triethoxysilane (APS) (1) modified ITO, ITO or ATO electrode. Linear growth of the films electroactivity with the number of cascade steps is observed for up to 12 cascade steps yielding 1.1 x 10(-8) ferrocene centers/cm(2) on a flat ITO electrode, whereas 3 cascade steps yield 2.2 x 10(-7) ferrocene centers/cm(2) on a mesoporeous ATO electrode. In case of the ATO electrode, the inner walls of the mesopores exhibiting a very large surface are completely modified in the procedure. Beside this large coulometry fast electron transfer kinetics, high stability and low optical density in both oxidation states is observed.The electrodes were checked for their potential use as optically transparent counter electrodes in electrochromic devices. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2004.05.022

文献信息

• Ferrocene Encapsulated within Symmetric Dendrimers:  A Deeper Understanding of Dendritic Effects on Redox Potential
  作者：Diane L. Stone、David K. Smith、P. Terry McGrail

  DOI：10.1021/ja0117478

  日期：2002.2.1

  Ferrocene has been encapsulated within a symmetric ether-amide dendritic shell and its redox potential monitored in a variety of solvents. The dendritic effect generated by the branched shell is different in different solvents. In less polar, non hydrogen bond donor solvents, attachment of the branched shell to ferrocene increases its E-1/2, indicating that oxidation to ferrocenium (charge buildup) becomes thermodynamically hindered by the dendrimer, a result explained by the dendrimer providing a less polar medium than that of the surrounding electrolyte solution. The effect of electrolyte concentration on redox potential was also investigated, and it was shown that the concentration of "innocent" electrolyte has a significant effect on the redox potential by increasing the overall polarity of the surrounding medium. Dendritic destabilization of charge buildup is in agreement with the majority of reported dendritic effects. A notable exception to this is provided by the asymmetric ferrocene dendrimers previously reported by Kaifer and co-workers, in which the branching facilitated oxidation, and it is proposed that in this case the dendritic effect is generated by a different mechanism. Interestingly, in methanol, the new symmetric ferrocene dendrimer exhibited almost no dendritic effect, a result explained by the ability of methanol to interact extensively with the branched shell, generating a more open superstructure. By comparison of all the new data with other reports, this study provides a key insight into the structure-activity relationships which control redox processes in dendrimers and also an insight into the electrochemical process itself.