2,3,5,6-tetramethyl-N,N'-bis(ortho-ethynylbenzene)-1,4-benzoquinone diimine | 1093622-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5,6-tetramethyl-N,N'-bis(ortho-ethynylbenzene)-1,4-benzoquinone diimine
• 英文别名: 1-N,4-N-bis(2-ethynylphenyl)-2,3,5,6-tetramethylcyclohexa-2,5-diene-1,4-diimine
• CAS: 1093622-61-7
• 化学式: C₂₆H₂₂N₂
• 分子量: 362.474
• InChiKey: PMSKJOGMTCNVPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  copper(l) iodide 、 顺-二氯双(三乙基膦)铂(II) 、 2,3,5,6-tetramethyl-N,N'-bis(ortho-ethynylbenzene)-1,4-benzoquinone diimine 在 ((CH₃)2CH)2NH 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到chlorocopper(I)-cyclo(2,3,5,6-tetramethyl-N,N'-bis(ortho-ethynylbenzene)-1,4-benzoquinone diimine)bis(triethylphosphine)platinum(II)
  参考文献：
  名称：

  Conjugated Organometallic Polymer Containing a Redox-Active Center

  摘要：

  The new conjugated organometallic polymer (-spacer-C C-Pt(PBu3)(2)-C C-)(n) (3; spacer = para-bis(diphenyl-(tetramethyl)quinone diimine) and the cyclic mononuclear model complex, spacer'-C C-Pt(PEt3)(2)-C C, CuCl (4; spacer' = ortho-diphenyl-2,3,5,6-tetramethyl-1,4-benzoquinone diimine) were synthesized from the 1:1 condensation of the corresponding diethynyl ligands (2-para and 2-ortho (para- and ortho-diethynyl-diphenyl-2,3,5,6-tetramethylquinone diimine), respectively), with the trans-Pt(PBu3)(2)Cl-2 for polymer 3 and cis-Pt(PEt3)(2)Cl-2 for 4. The materials were characterized by G PC, DSC, ATG, and electrochemistry for polymer 3, and by X-ray diffraction for 4. Polymer 3 exhibits a M, of 18500, M-w of 25000 with a PD of 1.37. The trans-geometry about Pt in polymer 3 was confirmed by(31) P NMR and IR/Raman spectroscopy. The cyclic voltammogram study on the model complex trans-Pt(PBu3)(2)(C CPh)(2), spacer 1-para (Me3Si-C C-R-C C-SiMe3; R = para-diphenyl-2,3,5,6-tetramethyl-1,4-benzoquinone diimine) and polymer 3 demonstrated that polymer 3 in the presence of trifluoroacetic acid (TFA) exhibits a quasi reversible 2-electron reduction process centered at 0.48 V versus SCE corresponding to the reduction of the protonated quinone diimine unit into the corresponding diamine. The UV-vis spectra of the spacer 2-para (440 nm) and polymer 3 (502 nm) are characterized by red-shifted charge transfer (CT) absorptions (C6H4C C -> quinone diimine for 2-para; and (C6H4C C)(2)Pt -> quinone diimine for polymer 3). These assignments are corroborated by density-functional theory (DFT) and time-dependent density-functional theory (TDDFT) computations. Polymer 3 is not luminescent in the solid state or in solution at 77 K and 298 K.

  DOI：

  10.1021/ic800857v