3'-diphenylphosphanyl-5-methyl-2,2':5',2''-terthiophene | 378790-21-7

• 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'-diphenylphosphanyl-5-methyl-2,2':5',2''-terthiophene
• 英文别名: 3'-(diphenylphosphino)-5-methyl-2,2':5',2''-terthiophene；Me-dppterth；PMeT3；[2-(5-Methylthiophen-2-yl)-5-thiophen-2-ylthiophen-3-yl]-diphenylphosphane；[2-(5-methylthiophen-2-yl)-5-thiophen-2-ylthiophen-3-yl]-diphenylphosphane
• CAS: 378790-21-7
• 化学式: C₂₅H₁₉PS₃
• 分子量: 446.598
• InChiKey: QQFNNJQMMUZGEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  3'-diphenylphosphanyl-5-methyl-2,2':5',2''-terthiophene 在 HCl 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (PdCl(p-tolylisocyanide)(3'-diphenylphosphino-5-methyl-2,2':5',2''-terthiophene-P,C3))
  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：

  2-溴-5-甲基噻吩 在 正丁基锂 、 溴 、 magnesium 作用下， 以 乙醚 、 正己烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 32.5h， 生成 3'-diphenylphosphanyl-5-methyl-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

• Reversible Molecular Switching of Ruthenium Bis(bipyridyl) Groups Bonded to Oligothiophenes:  Effect on Electrochemical and Spectroscopic Properties
  作者：Carolyn Moorlag、Michael O. Wolf、Cornelia Bohne、Brian O. Patrick

  DOI：10.1021/ja043573a

  日期：2005.5.1

  [Ru(bpy)(2)PT(3)-P,C]PF(6), [Ru(bpy)(2)PMeT(3)-P,C]PF(6), [Ru(bpy)(2)PMe(2)T(3)-P,C]PF(6), and [Ru(bpy)(2)PDo(2)T(5)-P,C]PF(6), where the thienyl carbon is bonded to ruthenium (P,C bonding). The P,C complexes revert back to the P,S bonding mode by reaction with acid; therefore, metal-thienyl bonding is reversibly switchable. The effect of interaction of the metal groups in the different bonding modes with

  这些配合物与碱反应，产生配合物 [Ru(bpy)(2)PT(3)-P,C]PF(6), [Ru(bpy)(2)PMeT(3)-P,C]PF (6), [Ru(bpy)(2)PMe(2)T(3)-P,C]PF(6), 和 [Ru(bpy)(2)PDo(2)T(5)-P, C]PF(6)，其中噻吩基碳与钌键合（P，C 键合）。P,C 配合物通过与酸反应恢复到 P,S 键合模式；因此，金属-噻吩键是可逆转换的。不同键合模式中金属基团与噻吩基骨架相互作用的影响反映在络合物固态结构中噻吩基环排列的变化、氧化还原电位和 pi --> pi 跃迁解决方案。连接到三噻吩基团的甲基取代基可以观察这些取代基对构象和电子特性的影响，并有助于电化学数据的分配。以 P、S 和 P、C 键合模式结合的 PT(n)() 配体也改变了钌双（联吡啶）基团的电化学和光谱特性。两种键合模式都会导致低聚噻吩发光的猝灭。对于 [R
• Electropolymerization of Pd(II) Complexes Containing Phosphinoterthiophene Ligands
  作者：Olivier Clot、Michael O. Wolf、Brian O. Patrick

  DOI：10.1021/ja016465m

  日期：2001.10.1

  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.