1-(2-azidoethyl)-2,5-dithiophen-2-yl-1H-pyrrole | 1435458-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-azidoethyl)-2,5-dithiophen-2-yl-1H-pyrrole
• 英文别名: 1-(2-Azidoethyl)-2,5-di-thiophen-2-yl-1h-pyrrole；1-(2-azidoethyl)-2,5-dithiophen-2-ylpyrrole
• CAS: 1435458-00-6
• 化学式: C₁₄H₁₂N₄S₂
• 分子量: 300.408
• InChiKey: WAIFZQAOONFFOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(N-卡唑)丙炔 、 1-(2-azidoethyl)-2,5-dithiophen-2-yl-1H-pyrrole 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以80%的产率得到9-[[1-[2-(2,5-Dithiophen-2-ylpyrrol-1-yl)ethyl]triazol-4-yl]methyl]carbazole
  参考文献：
  名称：

  含荧光基团的聚(2,5-二噻吩基吡咯)的光电性能

  摘要：

  In this study two new, fluorophore anchored 2,5-dithienylpyrrole derivatives (SNS-Carb, SNS-Flo) were successfully synthesized via click chemistry. Both monomers were subjected to electrochemical polymerization and the corresponding polymers (PSNS-Carb and PSNS-Flo) were thoroughly characterized for their electrochromic properties. PSNS-Carb displayed yellow to blue coloration in 1.31 s with a coloration efficiency of 120 cm(2) C-1 whereas PSNS-Flo revealed longer switching time (2.67 s) and lower coloration efficiency (78 cm(2) C-1). Coexistence of 3,4-ethylenedioxythiophene (EDOT) with SNS-Carb or SNS-Flo in polymerization media resulted in the formation of novel copolymer films (P1 and P2, respectively) having entirely diverged multichromic, superior optoelectronic properties. P1 revealed a switching time of 1.33 s, with a coloration efficiency of 164 cm2 C-1, whereas P2 exhibited a slower response time (1.87 s) with a lower coloration efficiency (155 cm(2) C-1), as in the case of their respective homopolymers. In general, P1 was shown to reveal higher Delta E values which indicate it's more noticeable and vivid color changing nature compared to P2. When the optoelectronic properties of homopolymers were compared with that of their respective copolymers, there was an explicit enhancement of the color pallet, switching time, optical contrast and coloration efficiency. (C) 2015 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.0311512jes
• 作为产物：
  描述：

  toluene-4-sulfonic acid 2-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)ethyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(2-azidoethyl)-2,5-dithiophen-2-yl-1H-pyrrole
  参考文献：
  名称：

  可点击的通用聚（2,5-二噻吩并吡咯）衍生物

  摘要：

  摘要在本研究中，合成并表征了一种基于1-（2-叠氮基-乙基）-2,5-二噻吩-2-基-1H-吡咯（SNS-N 3）的可单击的叠氮化物导电聚合物。研究了均聚物（PSNS-N 3）的光学和电子性质，并进行了比色研究。均聚物的带隙为2.49 eV，掺杂后显示黄色至蓝色。电化学制备的SNS-N 3和3,4-乙撑二氧噻吩（EDOT）的共聚物形成了多色，颜色可调的电致变色材料，具有从肉桂，芥末，柠檬绿，蓝色和深蓝色连续的颜色渐变。光谱电化学分析表明，中性共聚物具有两个吸收最大值（〜320和450 nm），其中两个的相对强度和位置取决于聚合电位。共聚物薄膜可以在约1.2秒内在中性和氧化形式之间完全转换，在950 nm处的透射率约为65％。另外，使用乙炔基二茂铁使PSNS-N 3涂布的ITO电极发生点击反应。CV和FTIR研究表明，二茂铁很容易附着在电极表面，而二茂铁和PSNS主链的电活性均不会损失。我们的结果表明，电化学制备的PSNS-N

  DOI：

  10.1016/j.reactfunctpolym.2013.03.014

文献信息

• Tuning of electrochromic properties of electrogenerated polythiophenes through Ru(II) complex tethering and backbone derivatization
  作者：Nese Guven、Hajar Sultanova、Burak Ozer、Baris Yucel、Pinar Camurlu

  DOI：10.1016/j.electacta.2019.135134

  日期：2020.1

  free counterparts (PEDOT, PProDOT and PSNS). The cathodic behavior of all polymers was mainly dominated by the redox and optical properties of the tethered Ru complex whereas their anodic behavior depended on properties of both the conjugated backbone and the Ru complex. Modification of conjugated backbone from SNS, ProDOT to EDOT led to a distinct variation of band gap from 2.44 eV, 1.94 eV–1.84 eV

  在这里，我们介绍了聚噻吩（PEDOT-Ru，PProDOT-Ru，PSNS-Ru）的电致变色性质，这些聚噻吩是通过束缚于[ Ru（bpy）2 pytri ] 2+的噻吩衍生物进行电化学聚合而合成的通过烷基链的配合物。非共轭间隔基阻碍了金属中心与聚合物主链之间的有效电子相互作用，从而为聚噻吩提供了与不含金属的对应物（PEDOT，PProDOT和PSNS）明显不同的多色和双极性性质。所有聚合物的阴极行为主要受束缚的Ru络合物的氧化还原和光学性质支配，而它们的阳极行为取决于共轭骨架和Ru络合物的性质。从SNS，ProDOT到EDOT的共轭骨架的修饰导致带隙从2.44 eV，1.94 eV–1.84 eV明显变化，并在中性状态下提供了宽范围的颜色（分别是黄色，橙色，绿色），这些颜色显然都是明显的与不含金属的同类产品不同。基于PEDOT的金属聚合物达到了46。24％的光学对比度和2.52 s的切换时
• A phosphorescent fluoride probe based on Eu(<scp>ııı</scp>)-DO3A clicked with a 2,5-di(thien-2-yl)pyrrole scaffold
  作者：Memduh Bilmez、Aysun Degirmenci、Melek Pamuk Algi、Fatih Algi

  DOI：10.1039/c7nj03569a

  日期：——

  The design, synthesis and physicochemical properties of a new phosphorescent fluoride probe 1 are described. The probe consists of a stable Eu(ııı) complex of a DO3A macrocycle on one side and a 2,5-di(thien-2-yl)pyrrole (SNS) scaffold on the other. They were linked together with a 1,2,3-triazole ring as a reliable connection unit, which was formed by Huisgen type copper-catalyzed [3+2] cycloaddition

  描述了新的磷光氟化物探针1的设计，合成和理化性质。该探针由一侧的DO3A大环的稳定Eu（ııı）配合物和另一侧的2,5-二（噻吩-2-基）吡咯（SNS）支架组成。它们与作为可靠连接单元的1,2,3-三唑环连接在一起，该环是由Huisgen型铜催化的叠氮化物和炔烃之间的[3 + 2]环加成反应形成的。这种新颖的材料可用作开启式磷光氟化物探针。据我们所知，这是将SNS单元与单击的Eu（ııı）组合在一起的第一个示例。）DO3A支架的复合物，可以诱导对其他阴离子中的氟离子的显着发光反应。最后，它为两输入或逻辑门行为使用OH还证明-和OAC -阴离子。
• Multichromic metallopolymers of poly(2,5-dithienylpyrrole)s derived through tethering of ruthenium(II) bipiridyl complex
  作者：Nese Guven、Baris Yucel、Hajar Sultanova、Pinar Camurlu

  DOI：10.1016/j.electacta.2022.140562

  日期：2022.8

  complexes and electrochemically polymerized to obtain a new class of electrochromic metallopolymers. The Ru-complexes were designed by altering the number of polymerizable SNS units per redox active metal center and the length of non-conjugated spacer, where the relationship between the monomer structure and optoelectronic properties of the resultant metallopolymers was investigated. Tuning of the native properties

  在这项研究中，2,5-二噻吩基吡咯 (SNS) 单元被束缚在钌 (II) 联吡啶配合物上，并通过电化学聚合得到一类新的电致变色金属聚合物。通过改变每个氧化还原活性金属中心的可聚合 SNS 单元的数量和非共轭间隔物的长度来设计 Ru 配合物，其中研究了单体结构与所得金属聚合物的光电性能之间的关系。通过引入电致变色钌络合物作为侧链取代基来调整聚 (2,5-二噻吩基吡咯) (PSNS) 的天然特性提供了一种可行的方法，其中金属聚合物不仅显示出双极性，而且还显示出充满活力的多色行为，显示出宽色域从红棕色到橙色到卡其色到灰色。通过研究具有联吡啶功能的类似聚 (2,5-二噻吩基吡咯) (PSNS) 的光电特性，揭示了衍生双极/多色活性的机制。发现单体中可聚合单元的数量主要影响电致变色性能并提高基于 SNS 的金属聚合物的光学对比度和着色效率。此处描述的基于 SNS 的金属聚合物的电致变色性能通过共聚将
• Electrosyntheses of anthracene clicked poly(thienylpyrrole)s and investigation of their electrochromic properties
  作者：Nese Guven、Pinar Camurlu

  DOI：10.1016/j.polymer.2015.07.005

  日期：2015.9

  A new anthracene containing thienylpyrrole derivative (SNS-Anth) was synthesized through click reaction of 9-((prop-2-yn-1-yloxy)methyl)anthracene with 1-(2-azidoethyl)-2,5-di(thiophen-2-yl)-1H-pyrrole(SNS-N-3). The chemical structure of SNS-Anth was confirmed by using H-1, C-13 NMR, FT-IR, UV-Vis, Fluoresence and mass spectroscopy techniques. SNS-Anth was subjected to electrochemical polymerization and the resultant polymer (PSNS-Anth) displayed green to blue coloration in 1.40 s with a coloration efficiency of 78 cm(2) C-1. The electrochemical copolymerization of SNS-Anth and 3,4-ethylenedioxythiophene (EDOT) was successfully achieved. The copolymer revealed distinct multi-chromic behavior where a wide pallet of esthetically pleasing colors (pinkish-red, orange, yellow, green and blue) was observed at various potentials. The objective evaluation of the colors of both PSNS-Anth and the copolymer at various potentials was performed through colorimetry studies on the basis of "Commission Internationale de l'Eclairage" (CIE) standards. The response time, optical contrast and coloration efficiency of the copolymer were calculated as 0.67 s, 28.88%, 193 cm(2) C-1 (at 900 nm), respectively. Considering the explicit spectral difference between PSNS-Anth and the copolymer, enhancement of the color pallet, switching time, optical contrast safely confirms formation of a true copolymer. (C) 2015 Elsevier Ltd. All rights reserved.