| 1321532-89-1

• CAS: 1321532-89-1
• 化学式: C₂₆H₁₈Fe₂N₂S
• 分子量: 502.202
• InChiKey: YRFFVUDCDRZGPU-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

• 作为产物：
  描述：

  2,5-二溴-1,3,4-噻二唑 、 二茂铁乙炔 在 NEt₃ 、 PdCl₂(PPh₃)2 、 CuI 作用下， 以 四氢呋喃 为溶剂， 以6%的产率得到
  参考文献：
  名称：

  Diferrocenes containing thiadiazole connectivities

  摘要：

  2,5-Diferrocenyl-1,3,4-thiadiazole, 2,5-Fc(2)-(C2N2S)-C-c, (3) has been synthesized by a two-fold Negishi ferrocenylation of dibromothiadiazole (1) with FcZnCl (2) (Fc = Fe(eta(5)-C5H4)(eta(5)-C5H5)) in presence of [Pd(Ph3P)(4)] as catalyst. Additional spacer units between the ferrocenyls and the (C2N2S)-C-c core could be introduced by using the Sonogashira C, C cross-coupling protocol. Reaction of 2,5-Br-2-(C2N2S)-C-c (1) or 2,5( C6H4-4'-I)(2)-(C2N2S)-C-c (6) with FcC equivalent to CH (4) using [PdCl2(Ph3P)(2)] and [CuI] as catalyst produced the appropriate organometallics 2,5-(FcC equivalent to)(2)-(C2N2S)-C-c (5) or 2,5-(C6H4-4'-C equivalent to CFc)(2)-(C2N2S)-C-c (7). The electronic and structural properties of 3, 5, and 7 were investigated with UV-Vis spectroscopy and single crystal Xray diffraction (3). Complex 3 adopts a solid state structure with none of the ferrocenyl substituents being coplanar with the thiadiazole ring. Cyclic, square wave, linear sweep voltammetry and in-situ NIR spectro-electrochemistry highlight the electrochemical properties of 3. In dichloromethane (0.1 mol L-1 [N(Bu-n)(4)][B(C6F5)(4)]), compound 3 displays two well resolved electrochemical reversible one-electron events with formal reduction potentials of 0.192 and 0.338 V versus FcH/FcH(+). In contrast, in presence of [N(Bu-n)(4)][PF6], the thiadiazoles 3 (E-0 = 0.22 V), 5 (E-0 = 0.18 V) and 7 (E-0 = 0.09 V) show simultaneously oxidation of the two ferrocenyl termini versus FcH/FcH+. Spectro-electrochemical studies, performed in a dichloromethane solution of 0.2 mol L-1 [N(nBu) 4][B(C6F5) 4], also show that 3 can successively be oxidized via 3(+) to 32(+). A weak IVCT absorption (epsilon ca. 300 L mol(-1) cm(-1)) at 1560 nm was found and is consistent with appreciable interactions between neutral ferrocenyl and positively charged ferrocenium mixed valent intermediates. Mixed-valent compound 3+ corresponds to a class II molecule according to Robin and Day. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.02.058