2-(2,5-dimethoxyphenyl)thiophene | 307951-13-9

• 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-(2,5-dimethoxyphenyl)thiophene
• CAS: 307951-13-9
• 化学式: C₁₂H₁₂O₂S
• 分子量: 220.292
• InChiKey: XYYWZUHWTNQVLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,5-dimethoxyphenyl)thiophene 在 正丁基锂 、 iron(III)-acetylacetonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以15%的产率得到5,5'-bis-(2,5-dimethoxyphenyl)-2,2'-bithiophene
  参考文献：
  名称：

  Discrete Photopatternable π-Conjugated Oligomers for Electrochromic Devices

  摘要：

  Three discrete oligomeric systems including an all-thiophene (T6) system, a thiophene/phenylene (TPTTPT) system, and a thiophene/EDOT/phenylene (TPEEPT) system have been constructed and characterized with emphasis on structural, optical, electrochemical, and spectroelectrochemical properties. For all three chromophores, the radical cation, the dication, and the 7r-dimer have been identified and characterized. EPR spectroscopy reveals that the radical cations of TPTTPT and TPEEPT have g values of 2.008-2.012 and peak-to-peak widths in the range 4.2-5.3 G. Formation of the radical cation takes place at a lower potential for TPEEPT than for TPTTPT and T6, whereas subsequent oxidation to the dication occurs more easily for TPTTPT than for TPEEPT and T6. We ascribe this observation to more localized charges in the oxidized species of TPEEPT, which is supported by our finding that the radical cation of TPEEPT is less prone to undergo 7r-dimerization than the radical cations of TPTTPT and T6. All the oxidized species are sufficiently stable to allow for optical characterization, and the relative positions of all absorption bands are found to be in agreement with the electrochemical data. For further solid-state modifications of these materials, we have effectively modified the synthetic design and grafted terminal functionalities (e.s. acrylates) onto the discrete oligorners. Of these novel materials, TPEEPT proves to be the most promising anodically coloring material for electrochromics, and it undergoes reversible switching between two different colored states (bright yellow and clear blue) and one almost transparent and color neutral state. Contrast ratios, measured as 0%Tat Amax, are as high as 62.5%, and switching times are in the range 2-5 s for the coloration process, though significantly longer for the bleaching process. As a proof of concept, we have successfully constructed a simple photopatterned electrochromic device by exploiting the terminal acrylate functionalities of the oligomers in a UV-initiated cross-linking process. To the best of our knowledge, this is the first oligomer-based photopatterned electrochromic device reported in the literature.

  DOI：

  10.1021/ja7112273
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基苯 、 2-(trimethylstannyl)thiophene 在 copper(l) iodide 、 cesium fluoride 、 palladium dichloride 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到2-(2,5-dimethoxyphenyl)thiophene
  参考文献：
  名称：

  Discrete Photopatternable π-Conjugated Oligomers for Electrochromic Devices

  摘要：

  Three discrete oligomeric systems including an all-thiophene (T6) system, a thiophene/phenylene (TPTTPT) system, and a thiophene/EDOT/phenylene (TPEEPT) system have been constructed and characterized with emphasis on structural, optical, electrochemical, and spectroelectrochemical properties. For all three chromophores, the radical cation, the dication, and the 7r-dimer have been identified and characterized. EPR spectroscopy reveals that the radical cations of TPTTPT and TPEEPT have g values of 2.008-2.012 and peak-to-peak widths in the range 4.2-5.3 G. Formation of the radical cation takes place at a lower potential for TPEEPT than for TPTTPT and T6, whereas subsequent oxidation to the dication occurs more easily for TPTTPT than for TPEEPT and T6. We ascribe this observation to more localized charges in the oxidized species of TPEEPT, which is supported by our finding that the radical cation of TPEEPT is less prone to undergo 7r-dimerization than the radical cations of TPTTPT and T6. All the oxidized species are sufficiently stable to allow for optical characterization, and the relative positions of all absorption bands are found to be in agreement with the electrochemical data. For further solid-state modifications of these materials, we have effectively modified the synthetic design and grafted terminal functionalities (e.s. acrylates) onto the discrete oligorners. Of these novel materials, TPEEPT proves to be the most promising anodically coloring material for electrochromics, and it undergoes reversible switching between two different colored states (bright yellow and clear blue) and one almost transparent and color neutral state. Contrast ratios, measured as 0%Tat Amax, are as high as 62.5%, and switching times are in the range 2-5 s for the coloration process, though significantly longer for the bleaching process. As a proof of concept, we have successfully constructed a simple photopatterned electrochromic device by exploiting the terminal acrylate functionalities of the oligomers in a UV-initiated cross-linking process. To the best of our knowledge, this is the first oligomer-based photopatterned electrochromic device reported in the literature.

  DOI：

  10.1021/ja7112273

文献信息

• Comprehensive Analysis of Fragment Orbital Interactions to Build Highly π-Conjugated Thienylene-Substituted Phenylene Oligomers
  作者：Jean-Charles Florès、Marie-Agnès Lacour、Xavier Sallenave、Françoise Serein-Spirau、Jean-Pierre Lère-Porte、Joël J. E. Moreau、Karinne Miqueu、Jean-Marc Sotiropoulos、David Flot

  DOI：10.1002/chem.201203869

  日期：2013.6.3

  π‐Conjugated thienylenephenylene oligomers with fluorinated and dialkoxylated phenylene fragments have been designed and prepared to understand the interactions in fragment orbitals, the influence of the substituents (F, OMe) on the HOMO–LUMO gap, and the role of intramolecular non‐covalent cumulative interactions in the construction of π‐conjugated nanostructures. Their strong conjugation was also

  设计并制备了具有氟化和二烷氧基化亚苯基片段的π共轭亚苯基亚苯基低聚物，以了解片段轨道上的相互作用，取代基（F，OMe）对HOMO-LUMO间隙的影响以及分子内非分子的作用共轭累积相互作用的π共轭纳米结构的建设。紫外光电子能谱和理论计算也证明了它们在气相中的强烈共轭。这些结果可以用二甲氧基亚苯基的π轨道的相对能级位置在确定π/π *中的关键作用来解释。氟化亚苯基实体的轨道水平。二烷氧基亚苯基提高了HOMO轨道，而氟化亚苯基降低了低聚物中的LUMO轨道。此外，氟化亚苯基噻吩化合物中S⋅⋅⋅F和H⋅⋅⋅F相互作用的存在会增加混合目标中S⋅⋅⋅O的相互作用，并有助于低聚物的完全共轭，从而导致弱共价。所涉及的芳族循环之间的环间角。这些结果表明π系统的扩展共轭，这是由狭窄的HOMO-LUMO间隙（根据DFT计算）和相对强的最大波长（由TD-DFT计算和实验性UV / Vis测量获得）所证实的。两种
• How to Build Fully π-Conjugated Architectures with Thienylene and Phenylene Fragments
  作者：Sandrine Lois、Jean-Charles Florès、Jean-Pierre Lère-Porte、Françoise Serein-Spirau、Joël J. E. Moreau、Karinne Miqueu、Jean-Marc Sotiropoulos、Patrick Baylère、Monique Tillard、Claude Belin

  DOI：10.1002/ejoc.200601114

  日期：2007.8

  A series of small-sized model π-conjugated oligomers have been prepared from thienylene and phenylene or dimethylor dimethoxy-substituted phenylene units. Crystallographic data for the methoxylated compound show a quasi-planar conformation with a non-covalent S–O interaction. The resulting strong conjugation in the gas phase has also been highlighted by UV/photoelectron spectroscopy and theoretical

  已经从噻吩基和亚苯基或二甲基或二甲氧基取代的亚苯基单元制备了一系列小型模型 π 共轭低聚物。甲氧基化合物的晶体学数据显示具有非共价 S-O 相互作用的准平面构象。紫外/光电子能谱和理论计算 (DFT) 也强调了气相中由此产生的强共轭。实际上，对于这些化合物，存在由分离的亚苯基-亚苯基物质的分子轨道之间的相互作用引起的大能隙ΔEπ。这可以用二甲氧基亚苯基单元的两个 π 轨道的能量来解释，这些分子轨道在三轨道相互作用图中的形状以及 S···O 相互作用的存在，重新介绍 π-共轭有机聚合物由于其直接相关的大量应用而受到了很多关注。沿着聚合物主链存在扩展的共轭 π 系统。由于其显着的电子和电光特性，它们在电子和光电器件的设计中引起了极大的兴趣，例如有机场效应晶体管 (OFET)、有机发光二极管 (OLED) 或太阳能电池[1,2]由于它们的分子和超分子化学性质，它们很容易调整。在比较显着的例子中，
• US3966769A
  申请人：——

  公开号：US3966769A

  公开（公告）日：1976-06-29
• [DE] PHOTOAKTIVES, ORGANISCHES MATERIAL FÜR OPTOELEKTRONISCHE BAUELEMENTE<br/>[EN] PHOTOACTIVE, ORGANIC MATERIAL FOR OPTOELECTRONIC COMPONENTS<br/>[FR] MATÉRIAU ORGANIQUE, PHOTO-ACTIF POUR COMPOSANTS OPTOÉLECTRONIQUES
  申请人：HELIATEK

  公开号：WO2014128277A1

  公开（公告）日：2014-08-28

  Die Erfindung betrifft Verbindungen der allgemeinen Formel A-D-A`, wobei der Donorblock unsymmetrisch ist, und deren Verwendung in optoelektronischen Bauelementen.