1,1'-bis((1H-imidazol-1-yl)methyl)ferrocene | 713108-26-0

• 英文名称: 1,1'-bis((1H-imidazol-1-yl)methyl)ferrocene
• 英文别名: 1,1'-bis(imidazolylmethyl)ferrocene
• CAS: 713108-26-0
• 化学式: C₁₈H₁₈FeN₄
• 分子量: 346.215
• InChiKey: MADJDIKIVIHHTO-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：

  ammonium hexafluorophosphate 、 1,1'-bis((1H-imidazol-1-yl)methyl)ferrocene 、 1,8-双(溴甲基)萘 以 乙腈 为溶剂， 以40.8%的产率得到
  参考文献：
  名称：

  基于咪唑鎓的大环化合物作为阴离子的多信号化学传感器

  摘要：

  一系列结构新颖的阴离子受体3，4和5，其中二茂铁单元和荧光部分链接到两个咪唑环已设计并从1,1'-双（咪唑基甲基）二茂铁制备。其晶体结构表明，这些受体能够结合阴离子，例如PF的6 -和Br - 。因此，使用多种技术进行了阴离子结合研究，包括电化学（简历 和 OSWV），荧光， 紫外线可见， 和 1 H NMR光谱。所有的受体显示到F特殊电化学响应-阴离子与超过260毫伏的一个显着的阴极移位并显示与F一个独特的选择性-和ACO -用荧光增强超过本感兴趣的各种其它阴离子（氯阴离子- ，溴- ，我-，HSO 4 -，H 2 PO 4 - ）。此外，对于受体5中，观察到明显的吸收变化为H时2 PO 4 -溶液中加入阴离子，而其它阴离子（F - ，氯- ，溴-我-，ACO -，HSO 4 - ）显示出仅在UV-VIS光谱的影响较小。1个1 H NMR滴定证明了受体3和4可以通过（C-H）结合阴离子+

  DOI：

  10.1039/b719115d
• 作为产物：
  描述：

  1,1'-dihydroxymethylferrocene 、 N,N'-羰基二咪唑 以 乙腈 为溶剂， 以65%的产率得到1,1'-bis((1H-imidazol-1-yl)methyl)ferrocene
  参考文献：
  名称：

  基于咪唑鎓的大环化合物作为阴离子的多信号化学传感器

  摘要：

  一系列结构新颖的阴离子受体3，4和5，其中二茂铁单元和荧光部分链接到两个咪唑环已设计并从1,1'-双（咪唑基甲基）二茂铁制备。其晶体结构表明，这些受体能够结合阴离子，例如PF的6 -和Br - 。因此，使用多种技术进行了阴离子结合研究，包括电化学（简历 和 OSWV），荧光， 紫外线可见， 和 1 H NMR光谱。所有的受体显示到F特殊电化学响应-阴离子与超过260毫伏的一个显着的阴极移位并显示与F一个独特的选择性-和ACO -用荧光增强超过本感兴趣的各种其它阴离子（氯阴离子- ，溴- ，我-，HSO 4 -，H 2 PO 4 - ）。此外，对于受体5中，观察到明显的吸收变化为H时2 PO 4 -溶液中加入阴离子，而其它阴离子（F - ，氯- ，溴-我-，ACO -，HSO 4 - ）显示出仅在UV-VIS光谱的影响较小。1个1 H NMR滴定证明了受体3和4可以通过（C-H）结合阴离子+

  DOI：

  10.1039/b719115d

文献信息

• The First (Ferrocenylmethyl)imidazolium and (Ferrocenylmethyl)triazolium Room Temperature Ionic Liquids
  作者：Ye Gao、Brendan Twamley、Jean'ne M. Shreeve

  DOI：10.1021/ic049961v

  日期：2004.5.1

  N-(Ferrocenylmethyl)imidazole (3a), 1-(ferrocenylmethyl)-1,2,4-triazole (3b), 1,1'-bis[(1H-imidazol-1-yl)methyl]ferrocene (8a), 1,1'-bis [(1H-(2-methyl)imidazol-1-yl)methyl]ferrocene (8b), and 1,1'-bis[(1H-1,2,4-triazol-1-yl)methyl]ferrocene (8c) were synthesized in moderate yields. These compounds were quaternized with methyl iodide to form 1-(ferrocenylmethyl)-3-methylimidazolium iodide (4a), 1-(ferrocenylmethyl)-4-methyl-1,2,4-triazolium iodide (4b), 1,1'-bis[1-(2,3-dimethyl)imidazolium]methyl}ferrocene diiodide (9b), and 1,1'-bis[1-(4-methyl)-1,2,4-triazolium]methyl}ferrocene diiodide (9c), respectively, in excellent yields. Compounds 4a, 4b, 9b, and 9c were metathesized with bis(trifluoromethanesulfonyl)amide to give high yields of 5a, 5b, 10b, and 10c. With potassium hexafluorophosphate, 9b forms 10d. Salts 5a, 5b, and 10c are the first room-temperature ionic liquids with cations containing an organometallic moiety that exhibit T-g values well below room temperature, i.e., -32, -16, and -11 degreesC. The compounds were characterized by H-1, F-19, and C-13 NMR, MS, and elemental analyses. T-g values and melting points were determined by DSC. T-d values (5% weight loss temperature) were recorded by TGA. X-ray single-crystal structures show that 9c and 10d crystallize in the triclinic space group P (1) over bar.
• Synthesis and Anion Sensing of Water-Soluble Metallomacrocycles
  作者：Liao-Yuan Yao、Lin Qin、Ting-Zheng Xie、Yi-Zhi Li、Shu-Yan Yu

  DOI：10.1021/ic200047t

  日期：2011.7.4

  The self-assembly of (TMEDA)Pd(NO(3))(2) or (TMEDA)Pt(NO(3))(2) (where TMEDA = N(1),N(1),N(2),N(2)-tetramethylethane-1,2-diamine) and anthracene- or ferrocene-based diimidazole ligands (L(1-3)) in aqueous solution affords a series of positively charged [M(2)L(2)](4+) dimetallomacrocycles. Their structures were characterized by (1)H NMR and electrospray ionization mass spectrometry and in the cases of [(TMEDA)Pd](2)L(2)(1)}(NO(3))(4) (1), [(TMEDA)Pd](2)L(2)(1)}(PF(6))(4) (1a), and [(TMEDA)Pd](2)L(2)(3)}(NO(3))(4) (4) by single-crystal X-ray diffraction analysis. Interestingly, the NMR spectra of 1 and la revealed that the difference of their structures, as confirmed by X-ray diffraction analysis, was that a NO(3)(-) of 1 was encapsulated inside the cavity of the basket-shaped metallomacrocycle by C-H center dot center dot center dot O hydrogen bonds, while PF(6)(-) of 1a was bound outside by C-H center dot center dot center dot F hydrogen bonds. The fluorescence titration experiment exhibited the formation of 1:1 host guest complexation for anthracene-based positively charged [M(2)L(2)](4+)-type metallomacrocycles with NO(3)(-). The interactions between metallomacrocycles and various anions were investigated via fluorescence titration and cyclic voltammetry studies, respectively.