2,5-二氯-3,4-乙烯基二氧噻吩 | 225518-49-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-二氯-3,4-乙烯基二氧噻吩
• 中文别名: 5,7-二氯-2,3-二氢噻吩3,4-b1,4二噁英
• 英文名称: 2,5-dichloro-3,4-ethylenedioxythiophene
• 英文别名: 5,7-Dichloro-2,3-dihydrothieno[3,4-b][1,4]dioxine
• CAS: 225518-49-0
• 化学式: C₆H₄Cl₂O₂S
• 分子量: 211.069
• InChiKey: UOJXEABHQWNIKN-UHFFFAOYSA-N

物化性质

• 熔点：
  65.0 to 69.0 °C
• 沸点：
  271.0±40.0 °C(Predicted)
• 密度：
  1.602±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2,5-二氯-3,4-乙烯基二氧噻吩 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以51%的产率得到5-chloro-2,3-dihydrothieno[3,4-b][1,4]dioxine
  参考文献：
  名称：

  Chain-Growth Polymerization of 2-Chlorothiophenes Promoted by Lewis Acids

  摘要：

  Lewis acids promote the polymerization of several 2-chloroalkylenedioxythiophenes, providing high-molecular-weight conjugated polymers. The proposed mechanism is a cationic chain-growth polymerization, as confirmed by end-capping reactions and a linear correlation of molecular weight with percent conversion. The "living" character of this process was used to prepare new block copolymers.

  DOI：

  10.1021/ja308498h
• 作为产物：
  描述：

  3,4-乙烯二氧噻吩 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以57%的产率得到2,5-二氯-3,4-乙烯基二氧噻吩
  参考文献：
  名称：

  Selective and general exhaustive cross-coupling of di-chloroarenes with a deficit of nucleophiles mediated by a Pd–NHC complex

  摘要：

  我们报告了在核苷酸亏缺的情况下，通过高活性的PEPPSI-IPent催化剂介导的Pd介导的多氯芳烃的普遍、全面的交叉偶联的首个示例。

  DOI：

  10.1039/c4cc08920k

文献信息

• Helical Carbon and Graphite Films Prepared from Helical Poly(3,4-ethylenedioxythiophene) Films Synthesized by Electrochemical Polymerization in Chiral Nematic Liquid Crystals
  作者：Satoshi Matsushita、Bairu Yan、Shinsuke Yamamoto、Yong Soo Jeong、Kazuo Akagi

  DOI：10.1002/anie.201308462

  日期：2014.2.3

  Helical carbon and graphite films from helical poly(3,4‐ethylenedioxythiophene) (H‐PEDOT) films synthesized through electrochemical polymerization in a chiral nematic liquid‐crystal (N*‐LC) field are prepared. The microscope investigations showed that the H‐PEDOT film synthesized in the N*‐LC has large domains of one‐handed spiral morphology consisting of fibril bundles. The H‐PEDOT films exhibited

  从手性向列液晶（N * -LC）场中通过电化学聚合合成的螺旋聚（3,4-乙撑二氧噻吩）（H-PEDOT）膜制备了螺旋碳和石墨膜。显微镜研究表明，在N * -LC中合成的H-PEDOT膜具有由原纤维束组成的单螺旋形态的大区域。H-PEDOT膜在圆二色性光谱中表现出明显的棉花效应。螺旋间距小于​​1μm的高度扭曲的N * -LC产生了具有高度有序形态的H-PEDOT膜。在800°C的温度下，从H-PEDOT膜制备的碳膜观察到带有左旋和右旋螺钉的螺旋形貌，并且与N * -LC的织构和螺旋节距密切相关。
• Solid-State Synthesis of a Conducting Polythiophene via an Unprecedented Heterocyclic Coupling Reaction
  作者：Hong Meng、Dmitrii F. Perepichka、Michael Bendikov、Fred Wudl、Grant Z. Pan、Wenjiang Yu、Wenjian Dong、Stuart Brown

  DOI：10.1021/ja037115y

  日期：2003.12.1

  Prolonged storage (similar to2 years) or gentle heating (50-80 degreesC) of crystalline 2,5-dibromo-3,4-ethylenedioxythiophene (DBEDOT) affords a highly conducting, bromine-doped poly(3,4-ethylenedioxythiophene) (PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR spectroscopies. The novel solid-state polymerization (SSP) does not occur for 2,5-dichloro-3,4-ethylenedioxythiophene (DCEDOT), and requires a much higher temperature (>130 degreesC) for 2,5-diiodo-3,4-ethylenedioxythiophene (DIEDOT). X-ray structural analysis of the above dihalothiophenes reveals short Hal...Hal distances between adjacent molecules in DBEDOT and DIEDOT, but not in DCEDOT. The polymerization may also occur in the melt but is significantly slower and leads to poorly conductive material. Detailed studies of the reaction were performed using ESR, DSC, microscopy, and gravimetric analyses. SSP starts on crystal defect sites; it is exothermic by 14 kcal/mol and requires activation energy of similar to26 kcal/mol (for DBEDOT). The temperature dependence of the conductivity of SSP-PEDOT (sigma(rt) = 20-80 S/cm) reveals a slight thermal activation. It can be further increased by a factor of 2 by doping with iodine. Using this approach, thin films of PEDOT with conductivity as high as 20 S/cm were fabricated on insulating flexible plastic surfaces.
• Processes for preparing conductive macromolecular polythiophenes
  申请人：Myongji University

  公开号：US20040171790A1

  公开（公告）日：2004-09-02

  The present invention relates to a process for preparing polythiophenes comprised of unit structures of the general formula 1: 1 where R 1 and R 2 independently represent hydrogen or a C 1 ˜C 4 alkyl group, or together represent an optionally substituted C 1 ˜C 4 alkylene group, preferably an optionally alkyl-substituted methylene group, an optionally C 1 ˜C 4 alkyl- or phenyl-substituted 1,2-ethylene group, a 1,3-propylene group or a 1,2-cyclohexylene group. More specifically, the process according to the present invention is characterized by the fact that it is performed by cationic polymerization from 2,5-dihalothiophene in the presence of an acid catalyst, such as Lewis acid, protic acid, oxygen acid, or polymeric acid. The conductivity of the resulting polythiophene is 255 S/cm under optimal conditions.
• US7034104B2
  申请人：——

  公开号：US7034104B2

  公开（公告）日：2006-04-25
• Thiophene π‐Bridge Manipulation of NIR‐II AIEgens for Multimodal Tumor Phototheranostics
  作者：Yixiong Gui、Yuanwei Wang、Deliang Wang、Yi Qin、Guangjie Song、Dingyuan Yan、Ben Zhong Tang、Dong Wang

  DOI：10.1002/anie.202318609

  日期：2024.4.2

  The fabrication of a multimodal phototheranostic platform on the basis of single‐component theranostic agent to afford both imaging and therapy simultaneously, is attractive yet full of challenges. The emergence of aggregation‐induced emission luminogens (AIEgens), particularly those emit fluorescence in the second near‐infrared window (NIR‐II), provides a powerful tool for cancer treatment by virtue of adjustable pathway for radiative/non‐radiative energy consumption, deeper penetration depth and aggregation‐enhanced theranostic performance. Although bulky thiophene π‐bridges such as ortho‐alkylated thiophene, 3,4‐ethoxylene dioxythiophene and benzo[c]thiophene are commonly adopted to construct NIR‐II AIEgens, the subtle differentiation on their theranostic behaviours has yet to be comprehensively investigated. In this work, systematical investigations discovered that AIEgen BT‐NS bearing benzo[c]thiophene possesses acceptable NIR‐II fluorescence emission intensity, efficient reactive oxygen species generation, and high photothermal conversion efficiency. Eventually, by using of BT‐NS nanoparticles, unprecedented performance on NIR‐II fluorescence/photoacoustic/photothermal imaging‐guided synergistic photodynamic/photothermal elimination of tumors was demonstrated. This study thus offers useful insights into developing versatile phototheranostic systems for clinical trials.