tetraethyl thiophene-2,5-diylbismethylphosphonate | 71702-74-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: tetraethyl thiophene-2,5-diylbismethylphosphonate
• 英文别名: 2,5-bis(diethylphosphonomethyl)thiophene；2,5-Bis(diethoxyphosphorylmethyl)thiophene
• CAS: 71702-74-4
• 化学式: C₁₄H₂₆O₆P₂S
• 分子量: 384.37
• InChiKey: ASHZCIUABYZDOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  488.3±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  99.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  双(2-噻吩)酮 、 tetraethyl thiophene-2,5-diylbismethylphosphonate 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 40.0h， 以40%的产率得到2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene
  参考文献：
  名称：

  Formation of a trithia[5]helicene in an unexpected photoreaction of a methyl-substituted bis(dithienylethenyl)thiophene through a double sequence of 6π-electrocyclization/aromatization (dehydrogenation/demethylation)

  摘要：

  Photochemical reactions of 2,5-bis[2,2-di(thien-2-yl)ethenyl]thiophene (1a) and its tetramethyl derivative 1b, under direct photoexcitation, and photoinduced electron-transfer conditions, were studied. Our initial prediction was that 1b would undergo a photoreaction as part of a reversible photochromic system, while a reaction of its non-methyl substituted analog 1a would undergo a typical double sequence of 6 pi-electrocyclization (6 pi-EC)/aromatization (AR) (double dehydrogenation, -2H) to give 7,11-di(thien-2-yl)trithia[5]helicene (2a). In fact, we observed that photoirradiation of 1b leads to formation of the 7,11-bis(3-methylthien-2-yl)trithia[5]helicene (2b). In this process, 2b is formed via a double sequence of 6 pi-EC/AR (dehydrogenation/demethylation, -H/-Me). Moreover, the yield of formation of 2b is much higher than that of 2a, which reacts through a double sequence of 6 pi-EC/AR (-2H). Thus, this photochemically-induced paradoxical cascade reaction based on the newly uncovered reactivity serves as an efficient method to construct the trithia[5]helicene framework. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.10.012
• 作为产物：
  描述：

  2,5-噻吩二羧酸 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 tetraethyl thiophene-2,5-diylbismethylphosphonate
  参考文献：
  名称：

  Tetraethylthiophene‐2,5‐diylbismethylphosphonate: A Novel Electrolyte Additive for High‐Voltage Batteries

  摘要：

  AbstractIn this work, a novel high‐voltage electrolyte additive, tetraethylthiophene‐2,5‐diylbismethylphosphonate (TTD), was synthesized, and the influence of TTD on the electrolyte and its electrochemical performance under different voltages were studied by changing the content of the TTD additive. The results showed that the TTD additive significantly improved the capacity, cycle stability, and rate capability of batteries when charging/discharging at high voltages. After adding 1 % TTD to the basic electrolyte, the capacity retention rate of batteries after 200 cycles at 4.2, 4.3, 4.4, and 4.5 V increased by 20.8, 18.3, 50, and 31.9 %, respectively. In addition, transmission electron microscopy (TEM) and X‐ray photoelectron spectroscopy (XPS) results showed that TTD could effectively inhibit the decomposition of the electrolyte and participate in the formation of a uniform, thin, and stable cathode electrolyte interphase (CEI) film on the electrode surface, thereby effectively inhibiting the side reaction between the electrolyte decomposition product and the CEI membrane, and finally improving the high‐voltage performance of the battery. The TTD additive may provide a cost‐effective solution for high‐performance high‐voltage electrolytes.

  DOI：

  10.1002/cssc.202101277

文献信息

• Synthesis of oligo(p-phenylene–vinylene–thienylene)s as potential red light-emitting materials
  作者：Cuihua Xue、Fen-Tair Luo

  DOI：10.1016/s0040-4020(03)00783-x

  日期：2003.7

  Several potential red light-emitting oligomers containing alkoxylated phenylene–vinylene–thienylene backbones with and without cyano groups at the olefin moieties have been designed and synthesized. The influences of the skeleton as well as the position of the cyano groups in the vinylene moiety to the absorption and emission spectra of these new oligomers are also discussed.

  设计并合成了几种潜在的红色发光低聚物，这些低聚物包含在烯烃部分带有和不带有氰基的烷氧基化亚苯基-亚乙烯基-亚噻吩基骨架。还讨论了骨架以及亚乙烯基部分中氰基的位置对这些新的低聚物的吸收和发射光谱的影响。
• Oligothiophene-2-yl-vinyl bridged mono- and binuclear ruthenium(II) tris-bipyridine complexes: Synthesis, photophysics, electrochemistry and electrogenerated chemiluminescence
  作者：Minna Li、Jianhui Liu、Licheng Sun、Jingxi Pan、Changzhi Zhao

  DOI：10.1016/j.jorganchem.2007.10.017

  日期：2008.1

  For the binuclear complexes these two absorption bands are overlapped. All the metal complexes have very weak emission compared to that of the reference complex Ru(bpy)2+3. The first reduction potentials of all mononuclear ruthenium complexes are less negative than that of Ru(bpy)2+3, due to the moderate electron-withdrawing effect of oligothienylenevinylenes. For binuclear ruthenium complexes, only

  已合成了一系列与单亚硫基亚乙烯基亚乙烯基系在一起的单核和双核钌（II）三联吡啶化合物，并通过1 H NMR，13 C NMR和TOF-MS光谱进行了表征。研究了这些配合物的光物理，电化学和电化学发光（ECL）性质。单核钌配合物的电子吸收光谱在MLCT（金属到配体的电荷转移）和低聚亚硫基亚乙烯基的π-π *跃迁处均显示出明显的红移，并伴随着硫代苯基-2-基-乙烯基单元数量的增加。对于双核络合物，这两个吸收带是重叠的。与参考配合物Ru（bpy）2+相比，所有金属配合物的发射都非常弱3。所有的单核钌配合物的第一还原电位都比Ru（bpy）2+ 3的负还原电位小，这是由于低聚亚硫基乙烯撑具有中等的吸电子作用。对于双核钌配合物，仅观察到一个Ru（II / III）氧化峰（E 1/2  = 0.96 V vs. Ag / Ag +），表明两个金属中心之间的相互作用较弱。除了RuTRu以外，所有钌配合物的
• Stepwise Unidirectional Synthesis of Oligo Phenylene Vinylenes with a Series of Monomers. Use in Plastic Solar Cells
  作者：Mikkel Jørgensen、Frederik C. Krebs

  DOI：10.1021/jo0506783

  日期：2005.7.1

  Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-2[4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropoxyphenyl] vinyl }benzyl)phosphonic acid diethyl ester, (5-2- [4-(5,5-dimethyl [1,31 dioxan-2-yl)-2,5-dipropylphenyl] vinyl }thiophene-2-yl-methyl)phosphonic acid diethyl ester, (5-2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropoxyphenyl]vinyl}thiophene-2-yl-methyl)phosphonic acid diethyl ester, and (7-2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5]thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C-60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.
• Functionalization of 3,4-ethylenedioxythiophene
  作者：A.K. Mohanakrishnan、André Hucke、Michael A. Lyon、M.V. Lakshmikantham、Michael P. Cava

  DOI：10.1016/s0040-4020(99)00485-8

  日期：1999.10

  Syntheses of 3,4-ethylenedioxythiophene-based vinylenes and oligomers are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Berlin, Anna; Bradamante, Silvia; Ferraccioli, Raffaella, Journal of the Chemical Society. Perkin transactions I, 1987, p. 2631 - 2636
  作者：Berlin, Anna、Bradamante, Silvia、Ferraccioli, Raffaella、Pagani, Giorgio A.、Sannicolo, Franco

  DOI：——

  日期：——