5-diphenylphosphino-2,2':5',2''-terthiophene | 378789-94-7

• 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: 5-diphenylphosphino-2,2':5',2''-terthiophene
• 英文别名: diphenyl(2,2':5',2''-terthienyl-5-yl)phosphine；2-diphenylphosphino-5,2':5',2''-terthiophene；3T-PPh2；PT3；5dppterth；Agn-PC-0nhvnb；diphenyl-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]phosphane
• CAS: 378789-94-7
• 化学式: C₂₄H₁₇PS₃
• 分子量: 432.571
• InChiKey: AMBNQFIOSFIDHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  potassium tetrachloroplatinate(II) 、 5-diphenylphosphino-2,2':5',2''-terthiophene 以 二氯甲烷 、 水 为溶剂， 以81%的产率得到(2-diphenylphosphino-5,2':5',2''-terthiophene)2PtCl2
  参考文献：
  名称：

  膦基-（低聚噻吩）钯（II）和铂（II）配合物中的分子间相互作用和电子特性

  摘要：

  已经制备了一系列含有二苯基膦取代的低聚噻吩配体的 Pt(II) 和 Pd(II) 配合物，长度范围为 1 到 3 个噻吩环。其中四种配合物的晶体结构是通过单 X 射线晶体衍射确定的，并且发现固态堆积排列随金属和含噻吩的配体而变化。在某些情况下，发现低聚噻吩配体的噻吩环之间存在 π 堆积。报道了这些配合物的溶液和固态吸收光谱。关键词：低聚噻吩，金属配合物，结构特性，电子光谱。

  DOI：

  10.1139/v07-033
• 作为产物：
  描述：

  alpha-三联噻吩 、 二苯基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以29%的产率得到5-diphenylphosphino-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

• Assembly of a terthiophene-containing metallamacrocycle
  作者：Tracey L. Stott、Michael O. Wolf、Anita Lam

  DOI：10.1039/b417969b

  日期：——

  A metallamacrocycle in which conjugated terthiophene groups link the metals is assembled from a labile Pd complex.

  一个由共轭噻吩基团连接金属的金属大循环是由一个易变钯络合物组装而成的。
• Field, John S.; Haines, Raymond J.; Lakoba, Elena I., Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 24, p. 3352 - 3360
  作者：Field, John S.、Haines, Raymond J.、Lakoba, Elena I.、Sosabowski, M. Hal

  DOI：——

  日期：——
• Structural and Electronic Properties of Phosphino(oligothiophene) Gold(I) Complexes
  作者：Tracey L. Stott、Michael O. Wolf、Brian O. Patrick

  DOI：10.1021/ic0493200

  日期：2005.2.1

  A series of gold(I) complexes containing phosphino(oligothiophene) ligands of varying conjugation length has been prepared. Solid state crystal structures of (PT3)AuCl (PT3 = 5-diphenylphosphino-2,2':5',2"-terthiophene) and AuCl-(PTP)AuCl (PTP = 2,5-diphenylphosphinothiophene) have been obtained. The complex AuCl(PTP)AuCl crystallizes as a dimer with two intermolecular Au-Au contacts. Variable temperature NMR spectroscopy is used to demonstrate the presence of aurophilic interactions in solution for Aul(PTP)Aul. Dual emission is observed for AuCl(PTP)AuCl in solution and is attributed to emission from both monomer and dimer. In the solid state, dimer emission is dominant. The iodo analogue, Aul(PTP)Aul, shows only low energy dimer emission in both solution and the solid state. Compounds in which the ligands contain longer bridges (either bithienyl or terthienyl) show absorption and emission bands due to the pi-pi* transition only, both in solution and the solid state.
• Synthesis and Characterization of Transition Metal Systems Containing Phosphino-Oligothiophene Ligands for Nonlinear Optical Materials
  作者：R. Dustan Myrex、Gary M. Gray、Amelia G. VanEngen Spivey、Christopher M. Lawson

  DOI：10.1021/om060224b

  日期：2006.10.1

  Polythiophenes exhibit interesting third-order nonlinear optical properties but poor solubilities. Incorporating polythiophenes into transition metal complexes should yield readily soluble materials, and the transition metal substituent may alter third-order nonlinear optical properties of the polythiophene. In this paper, we report the synthesis and characterization of 2-diphenylphosphinothianaphthene, A, and its trans-PdCl2L2, B, and cis-PtCl2L2, C, analogues. Additionally 2-diphenylphoshino-5:2',5':2"-terthiophene, D, its trans-PdCl2L2 complex, E, both first prepared by Wolf, 25 the previously unprepared cis- PtCl2L2 analogue, F, and the oxide of A, G, were prepared and investigated for nonlinear optical (NLO) behavior. No appreciable third-order NLO behavior was observed for A, D, or G. However both E and F exhibited nonlinear refraction, as shown by Z-scan measurements, and nonlinear absorption. The nonlinear absorption was significantly stronger for E, indicating that the metal center has a significant affect on nonlinear absorption. This is the first reported observation of this type of nonlinear behavior in metalphosphinothiophene systems.
• [W₆S₈] Octahedral Tungsten Clusters Functionalized with Thiophene Derivatives:  toward Polymerizable Building Blocks
  作者：Sandrine Perruchas、Samuel Flores、Bruno Jousselme、Emil Lobkovsky、Hector Abruña、Francis J. DiSalvo

  DOI：10.1021/ic7010748

  日期：2007.10.1

  The functionalization of octahedral [W6S8] Clusters with a family of phosphino-thiophene ligands has been investigated with the goal of synthesizing extended networks of [W6S8] units covalently linked to one another through thiophene-conjugated bridges. In addition to new phosphino-thiophene ligands, eight clusters were synthesized and characterized by H-1 and P-31 NMR spectroscopies, elemental analysis, and UV-vis absorption. These clusters are formulated [W6S8(T-PPh2)(6)] (1a), [W6S8(T-PEt2)(6)] (1b), [W6S8(2T-PPh2)(6)] (2a), [W6S8(2T-PEt2)(6)] (2b), [W6S8(3T-PPh2)(6)] (3a), [W(6)s(8)(3T-PEt2)(6)] (3b), [W6S8((2T)(3)P)(6)] (4), and [W6S8(2EDOT-PEt2)(6)] (5) (T = thiophene and EDOT = 3,4-ethylenedioxythiophene). The molecular structure of six of them has been obtained by single-crystal X-ray diffraction analysis. All of them crystallize in the P (1) over bar triclinic space group except 3b, which has the P2(1)/c monoclinic symmetry. The redox behavior of both the ligands and the corresponding functionalized clusters has been investigated by cyclic voltammetry. An attempt to electropolymerize these species is also reported.