2,5-diiodo-3,4-ethylenedioxythiophene | 640737-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-diiodo-3,4-ethylenedioxythiophene
• 英文别名: 5,7-diiodo-2,3-dihydrothieno[3,4-b][1,4]dioxine
• CAS: 640737-72-0
• 化学式: C₆H₄I₂O₂S
• 分子量: 393.972
• InChiKey: XNVYOUBEESESHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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-diiodo-3,4-ethylenedioxythiophene 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.5h， 生成 2,5-diethynyl-3,4-ethylenedioxythiophene
  参考文献：
  名称：

  可变带隙聚（亚芳基乙炔）共轭聚电解质

  摘要：

  使用钯介导的（Sonogashira）偶联化学已经制备了一系列的聚（亚芳基乙炔）（PAE）共轭聚电解质（CPE）。该系列由五对共享相同的聚（亚芳基乙炔）主链的聚合物组成。每对中的一个成员包含阴离子磺酸盐（R-SO 3 - ）侧基，而另一个构件含有阳离子双-烷基（RN + -RN +-R）侧基。聚（亚芳基亚乙炔基）骨架的重复单元结构由双（烷氧基）亚苯基-1,4-亚乙炔基单元与第二个亚芳基亚乙炔基部分交替组成，使用了五种不同的亚芳基，Ar = 1,4-苯基， 2,5-吡啶基（Py），2,5-噻吩基（Th），2,5-（3,4-乙二氧基）噻吩基（EDOT）和1,4-苯并[2,1,3]硫代二唑（BDT ）。不同的亚芳基单元会引起一系列聚合物在HOMO-LUMO带隙中的变化，从而导致一系列材料在400至550 nm的波长下显示最大吸收，而在440至600 nm的范围内显示最大荧光。在甲醇，水和甲醇/水

  DOI：

  10.1021/ma0611523
• 作为产物：
  描述：

  2,5-diacetoxymercuro-3,4-ethylenedioxythiophene 在 碘 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以55%的产率得到2,5-diiodo-3,4-ethylenedioxythiophene
  参考文献：
  名称：

  Solid-State Synthesis of a Conducting Polythiophene via an Unprecedented Heterocyclic Coupling Reaction

  摘要：

  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.

  DOI：

  10.1021/ja037115y

文献信息

• Spacer-Extended Bis-Ene-Yne Compounds: Scope, Limitations, and Properties
  作者：Daniel Lumpi、Paul Kautny、Viktor Carl、Barbara Pokorny、Brigitte Holzer、Rene Klaffenböck、Wolfgang Skranc、Berthold Stöger、Ernst Horkel、Christian Hametner、Johannes Fröhlich

  DOI：10.1002/ejoc.201800446

  日期：2018.9.9

  The thiophene fragmentation reaction towards bis ene‐yne‐compounds has been systematically investigated. The convenient accessibility of these multifunctional building blocks paths the way for novel applications in functional organic materials.

  噻吩对双烯炔化合物的裂解反应已得到系统地研究。这些多功能积木的便捷可及性为功能性有机材料中的新颖应用铺平了道路。
• Deprotonative Metalation of Functionalized Aromatics Using Mixed Lithium-Cadmium, Lithium-Indium, and Lithium-Zinc Species
  作者：Katia Snégaroff、Jean-Martial L'Helgoual'ch、Ghenia Bentabed-Ababsa、Tan Tai Nguyen、Floris Chevallier、Mitsuhiro Yonehara、Masanobu Uchiyama、Aïcha Derdour、Florence Mongin

  DOI：10.1002/chem.200901432

  日期：2009.10.5

  N′‐tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp=2,2,6,6‐tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2⋅TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated

  在CDCl原位混合物2 ⋅TMEDA;（0.5当量TMEDA = Ñ，Ñ，N' ，N'四甲基乙二胺）或的InCl 3与[李（TMP）]（TMP = 2,2,6,6（0.33当量） -tetramethylpiperidino;分别为1.5或1.3当量，）与氯化锌的前述混合物进行了比较2 ⋅TMEDA（0.5当量），用于他们的能力去质子苯甲醚，苯并噻唑，和嘧啶和[李（TMP）]（1.5当量）。[（TMPhref=https://www.molaid.com/MS_21891929 target="_blank">TMp）3当在室温下用于四氢呋喃中时，CdLi]被证明是最好的碱，随后用碘进行捕集证明了这一点。然后证明了Cd-Li碱适用于多种芳族化合物的金属化，包括带有反应性官能团的苯（CONEt 2，CO 2 Me，CN，COPh）或重卤素（Br，I）和杂环（来自呋喃） ，噻吩，吡咯，恶唑，噻唑，吡啶和二嗪系列）。得益于双重激活位置的五元杂环在室温下也被双去质子化。由此获得的芳族碳酸钙可参与钯催化的交叉偶联反应，或简单地用酰氯淬灭。
• Deprotonative cadmation of functionalized aromatics
  作者：Jean-Martial L’Helgoual’ch、Ghenia Bentabed-Ababsa、Floris Chevallier、Mitsuhiro Yonehara、Masanobu Uchiyama、Aïcha Derdour、Florence Mongin

  DOI：10.1039/b809543d

  日期：——

  This communication describes the deproto-metalation of a large range of aromatics including heterocycles using a newly developed lithium–cadmium base; the reaction proceeds at room temperature with an excellent chemoselectivity and efficiency, and proved to be regioselective in most cases.

  本文介绍了使用新开发的锂-镉碱对包括杂环在内的一系列芳香化合物的去质子化金属化反应。该反应在室温下进行，表现出极佳的化学选择性和效率，并在大多数情况下证明具有区域选择性。
• Clean and Efficient Iodination of Thiophene Derivatives
  作者：Frédéric Gohier、Jérémie Grolleau、Pierre Frère

  DOI：10.1055/s-0035-1560480

  日期：——

  Abstract Iodination of thiophene derivatives is realized using a simple, fast, and efficient methodology. Iodination of thiophene and 2- or 3-substituted or 3,4-disubstituted thiophenes with N-iodosuccinimide (NIS) activated with 4-toluenesulfonic acid in ethanol gives pure iodinated products that require no further purification. Iodination of thiophene derivatives is realized using a simple, fast

  摘要 噻吩衍生物的碘化是通过简单，快速和有效的方法实现的。噻吩和2-或3-取代或3,4-二取代的噻吩在乙醇中用4-甲苯磺酸活化的N-碘琥珀酰亚胺（NIS）进行碘化，得到纯碘化产物，无需进一步纯化。 噻吩衍生物的碘化是通过简单，快速和有效的方法实现的。噻吩和2-或3-取代或3,4-二取代的噻吩在乙醇中用4-甲苯磺酸活化的N-碘琥珀酰亚胺（NIS）进行碘化，得到纯碘化产物，无需进一步纯化。
• Phenothiazine Based Donor-Acceptor Compounds with Solid-State Emission in the Yellow to NIR Region and Their Highly Selective and Sensitive Detection of Cyanide Ion in ppb Level
  作者：Elumalai Ramachandran、Somasundaram A. A. Vandarkuzhali、Gandhi Sivaraman、Raghavachari Dhamodharan

  DOI：10.1002/chem.201800216

  日期：2018.8.1

  3 % and 9.0 %. The fluorophores showed high emission in the doped state as well when dispersed in polystyrene (PS) matrix with emission maximum ranging from 536 nm to 648 nm with quantum yield in the range 12.4 %–64.4 %. The presence of dicyanovinyl (DCV) group in both the fluorophores was exploited towards cyanide sensing in DMSO leading to turn‐on fluorescence emission with high selectivity and sensitivity

  四个新的新颖施主-受主（A-π-d-A，A-d-π-d-A）的化合物（1，图1b，2和2b中基于乙烯（EDOT）和吩噻嗪）（PTZ）我们已经合理设计和合成了从黄色到近红外（NIR）的固态发射。化合物 1b和2b呈薄膜形式的，分别在713 nm和696 nm处显示出最大发射，相应的绝对固态量子产率为3.3％和9.0％。当荧光团分散在聚苯乙烯（PS）基体中时，在掺杂状态下也显示高发射，最大发射范围为536 nm至648 nm，量子产率在12.4％至64.4％的范围内。二氰基乙烯基（DCV）组的两种荧光团的存在下在DMSO中朝向氰化物传感利用领先的低的检测限以接通荧光发射具有高的选择性和灵敏度为氰化物离子作为0.32μ米（8 ppb）的用于图1b和0.57μ米（14 PPB）为2b的。DFT和TTDFT计算表明，添加氰化物离子可阻止分子内电荷从供体（PTZhref=https://www.molaid.com/MS_154274 target="_blank">PTz或EDOT）转移到受体（DCV），从而将