3'-diphenylphosphino-5,5''-dimethyl-2,2':5',2''-terthiophene | 378790-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3'-diphenylphosphino-5,5''-dimethyl-2,2':5',2''-terthiophene
• 英文别名: Me2-dppterth；[2,5-Bis(5-methylthiophen-2-yl)thiophen-3-yl]-diphenylphosphane
• CAS: 378790-23-9
• 化学式: C₂₆H₂₁PS₃
• 分子量: 460.625
• InChiKey: IBKHIEONCXANLO-UHFFFAOYSA-N

物化性质

• 沸点：
  558.2±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  palladium dichloride 、 3'-diphenylphosphino-5,5''-dimethyl-2,2':5',2''-terthiophene 在 HCl 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 (Pd2(μ-Cl)2(3'-diphenylphosphino-5,5'-dimethyl-2,2':5',2''-terthiophene-P,C3)2)
  参考文献：
  名称：

  Electropolymerization of Pd(II) Complexes Containing Phosphinoterthiophene Ligands

  摘要：

  A series of Pd complexes of 3'-diphenylphosphino-2,2:5'2"-terthiophene (1a, dppterth) in which the metal is coordinated in three different modes have been,prepared and electropolymerized, resulting in the formation of conductive thin films. In [Pd-2(mu -Cl-2)(dppterth-P,C-3)(2)] (3a), the metal is P,C-coordinated, in. [PdCl2(dppterth-P)(2)] (4a) the coordination is monodentate via the phosphine, and in [Pd(dppterth-P,C-3)(dppterth-P, S-1)] [PF6] (5a) both P,C- and P,S-coordination modes are found. In 5a, the coordinated thiophene is hemilabile and may be displaced by reaction with more strongly coordinating ligands such as isocyanides, To probe the effect of blocking the a-position of the terthienyl moiety with methyl groups, 3'-diphenylphosphino-5-methyl-2,2':5'2"-terthiophene (1b, Me-dppterth) and 3'-diphenylphosphino-5,5"-dimethyl-2,2':5'2"-terthiophene (1c, Me-2-dppterth) were prepared, and the corresponding series of Pd complexes was synthesized. One of these complexes, [Pd(Me-2-dppterth-P,C-3)(Me-2-dppterth-P,S-1)] [PF6] (5c), has been crystallographically characterized. The electropolymerized films prepared, from 5a react with isonitriles, and shifts in the absorption spectra of the electropolymerized materials are observed upon reaction. A Pd complex has also been prepared from 5-diphenylphosphino-2,2':5,'2"-terihiophene (2, 5dppterth), and this complex has been electropolymerized. All the electropolymerized thin films have been characterized using EDX analysis, which demonstrates good correspondence with the elemental analysis of the respective monomers, and the maximum conductivities of the films are near 10(-4) S cm(-1). Comparing the electropolymerization behavior of the complexes, along with their electrochemical and spectroscopic data, allows conclusions to be drawn regarding the involvement of pi -delocalization and the metal group in the conductivity of the Materials.

  DOI：

  10.1021/ja016465m
• 作为产物：
  描述：

  二苯基氯化膦 、 3'-bromo-5,5''-dimethyl-2,2':5',2''-terthiophene 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 以52%的产率得到3'-diphenylphosphino-5,5''-dimethyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Electropolymerization of Pd(II) Complexes Containing Phosphinoterthiophene Ligands

  摘要：

  A series of Pd complexes of 3'-diphenylphosphino-2,2:5'2"-terthiophene (1a, dppterth) in which the metal is coordinated in three different modes have been,prepared and electropolymerized, resulting in the formation of conductive thin films. In [Pd-2(mu -Cl-2)(dppterth-P,C-3)(2)] (3a), the metal is P,C-coordinated, in. [PdCl2(dppterth-P)(2)] (4a) the coordination is monodentate via the phosphine, and in [Pd(dppterth-P,C-3)(dppterth-P, S-1)] [PF6] (5a) both P,C- and P,S-coordination modes are found. In 5a, the coordinated thiophene is hemilabile and may be displaced by reaction with more strongly coordinating ligands such as isocyanides, To probe the effect of blocking the a-position of the terthienyl moiety with methyl groups, 3'-diphenylphosphino-5-methyl-2,2':5'2"-terthiophene (1b, Me-dppterth) and 3'-diphenylphosphino-5,5"-dimethyl-2,2':5'2"-terthiophene (1c, Me-2-dppterth) were prepared, and the corresponding series of Pd complexes was synthesized. One of these complexes, [Pd(Me-2-dppterth-P,C-3)(Me-2-dppterth-P,S-1)] [PF6] (5c), has been crystallographically characterized. The electropolymerized films prepared, from 5a react with isonitriles, and shifts in the absorption spectra of the electropolymerized materials are observed upon reaction. A Pd complex has also been prepared from 5-diphenylphosphino-2,2':5,'2"-terihiophene (2, 5dppterth), and this complex has been electropolymerized. All the electropolymerized thin films have been characterized using EDX analysis, which demonstrates good correspondence with the elemental analysis of the respective monomers, and the maximum conductivities of the films are near 10(-4) S cm(-1). Comparing the electropolymerization behavior of the complexes, along with their electrochemical and spectroscopic data, allows conclusions to be drawn regarding the involvement of pi -delocalization and the metal group in the conductivity of the Materials.

  DOI：

  10.1021/ja016465m

文献信息

• Switchable thiophene coordination in Ru(ii) bipyridyl phosphinoterthiophene complexesElectronic supplementary information (ESI) available: synthetic details and characterization data for all complexes. See http://www.rsc.org/suppdata/cc/b2/b209035j/
  作者：Carolyn Moorlag、Olivier Clot、Michael O. Wolf、Brian O. Patrick

  DOI：10.1039/b209035j

  日期：2002.11.29

  Switching between P,S- and P,C coordination modes of 3′-phosphinoterthiophene to Ru(II) results in substantial differences in the electronic spectra and cyclic voltammetry of these complexes.

  3′-phosphinoterthiophene 与 Ru(II) 的 P,S- 和 P,C 配位模式之间的转换导致这些配合物的电子光谱和循环伏安特性出现很大差异。