N-[2-(2-ethoxyethoxy)ethyl]-3,4-propylenedioxypyrrole | 376395-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[2-(2-ethoxyethoxy)ethyl]-3,4-propylenedioxypyrrole
• 英文别名: 2-(2-{2-[3,4-(1,3-propylenedioxy)pyrrol-1-yl]ethoxy}ethoxy)ethanol；2-[2-[2-(3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrol-7-yl)ethoxy]ethoxy]ethanol
• CAS: 376395-10-7
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: ADTDJGYWWFUUAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2,3,3-tetramethyl-4,7,10-trioxa-3-siladodecan-12-yl 4-methylbenzenesulfonate 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-[2-(2-ethoxyethoxy)ethyl]-3,4-propylenedioxypyrrole
  参考文献：
  名称：

  3,4-Alkylenedioxypyrroles:  Functionalized Derivatives as Monomers for New Electron-Rich Conducting and Electroactive Polymers

  摘要：

  New functionalized derivatives of 3,4-ethylenedioxypyrrole (EDOP, 5a) and 3,4-(1,3-propylenedioxy)-pyrrole (ProDOP, 5b) as especially electron-rich monomers which yield highly electroactive and stable conducting polymers useful for a diverse set Of applications have been synthesized. N-Alkylations of ProDOP were carried out to yield a variety of ProDOP derivatives having alkyl, sulfonatoalkoxy, glyme, and glyme alcohol pendant chains. Iodization of EDOP and ProDOP via iodo-decarboxylation afforded iodo-functionalized derivatives useful for subsequent aryl coupling chemistry. N-Protection and formylation of EDOP, followed by Knoevenagel condensation of the resultant 2-formyl-EDOP with aryl acetonitrile derivatives, led to 1-cyano-2-(2-(3,4-ethylenedioxy-pyrryl))-1-(2-thienyl)vinylene (23) (Th-CNV-EDOP) and 1-cyano-2-(2-(3,4-ethylenedioxypyrryl))-1-(2-(3,4-ethylenedioxythienyl)vinylene (26) (EDOT-CNV-EDOP). A 14-crown-4-ether 34 based dioxypyrrole was synthesized with a cavity potentially useful for lithium ion coordination and sensing in the resultant electroactive polymer. C-Alkylated ProDOPs (43a, 43b, and 43c) containing octyl, ethylhexyl, and dioctyl substituents appended to the central methylene of the propylene bridge, were prepared as monomers for potentially soluble pi -conjugated polymers.

  DOI：

  10.1021/jo001620l

文献信息

• N-Substituted Poly(3,4-propylenedioxypyrrole)s:  High Gap and Low Redox Potential Switching Electroactive and Electrochromic Polymers
  作者：Gürsel Sönmez、Irina Schwendeman、Philippe Schottland、Kyukwan Zong、John R. Reynolds

  DOI：10.1021/ma021108x

  日期：2003.2.1

  cyclic voltammograms, with E1/2 < −0.1 V vs Fc/Fc+ (+0.2 V vs SCE), negative of the oxidation of water, as desired for materials having stable doped forms and long-lived redox switching properties. In addition, the presence of a sulfonate group at the end of the propyl chain in N-PrS PProDOP offers the possibility of self-doping along with water solubility of the polymer. As a result, N-PrS PProDOP exhibits

  据报道，一系列电致变色的N-取代的聚（3,4-亚丙二氧基吡咯）（PProDOPs）具有高（> 3 eV）电子带隙，彩色氧化掺杂形式以及易于获得的低氧化还原度的综合特性。潜力。通过使用甲基（Me），丙基（Pr），辛基（Oct），丙烷磺化（PrS）和乙氧基乙氧基乙醇（Gly）侧链，与未衍生化的聚合物相比，所得聚合物的π-π*跃迁的吸收度发生了蓝移。父母 例如，对于聚（N-乙氧基乙氧基乙醇ProDOP）（N-Gly PProDOP），该跃迁在306 nm（起始于365 nm）处显示最大值，从而为约200 nm的膜厚度提供无色且高度透明的中性聚合物，其透光率大于99％。N取代的PProDOPs显示非常清晰的循环伏安图，E 1/2 <-0.1 V vs. Fc / Fc +（+0.2 V vs. SCE），水氧化为负，这对于具有稳定掺杂形式的材料和长寿命的氧化还原开关特性。此外，在N -PrS PP
• Electrochromic polymers and polymer electrochromic devices
  申请人：University of Florida

  公开号：US20030174377A1

  公开（公告）日：2003-09-18

  The subject invention pertains to electrochromic polymers and polymer electrochromic devices. In a specific embodiment, two complementary polymers can be matched and incorporated into dual polymer electrochromic devices. The anodically coloring polymers in accordance with the subject invention can allow control over the color, brightness, and environmental stability of an electrochromic window. In addition, high device contrast ratios, high transmittance changes, and high luminance changes can be achieved, along with half-second switching times for full color change. Also provided are electrochromic devices such as advertising signage, video monitors, stadium scoreboards, computers, announcement boards, warning systems for cell phones, warning/information systems for automobiles, greeting cards, electrochromic windows, billboards, electronic books, and electrical wiring. The subject invention also provides for the use of complementary electrochromic polymers in the manufacture of electrochromic devices. In some embodiments, the devices of the invention can be prepared using metal vapor deposition or line patterning.

  本发明涉及电致变色聚合物和聚合物电致变色器件。在一个特定的实施例中，可以将两种互补的聚合物配对并纳入双聚合物电致变色器件中。根据本发明的阳极着色聚合物可以允许控制电致变色窗户的颜色、亮度和环境稳定性。此外，可以实现高对比度比、高透射率变化和高亮度变化，以及半秒钟的全彩色变换时间。还提供了电致变色器件，例如广告标志、视频监视器、体育场记分牌、计算机、公告牌、手机警告系统、汽车警告/信息系统、贺卡、电致变色窗户、广告牌、电子书和电气布线。本发明还提供了在制造电致变色器件时使用互补电致变色聚合物的方法。在一些实施例中，可以使用金属蒸汽沉积或线路图案制备本发明的器件。
• ELECTROCHROMIC POLYMERS AND POLYMER ELECTROCHROMIC DEVICES
  申请人：University of Florida

  公开号：EP1465962A1

  公开（公告）日：2004-10-13
• US6791738B2
  申请人：——

  公开号：US6791738B2

  公开（公告）日：2004-09-14
• [EN] ELECTROCHROMIC POLYMERS AND POLYMER ELECTROCHROMIC DEVICES<br/>[FR] POLYMERES ELECTROCHROMIQUES ET DISPOSITIFS ELECTROCHROMIQUES POLYMERIQUES
  申请人：UNIV FLORIDA

  公开号：WO2003046106A1

  公开（公告）日：2003-06-05

  The subject invention pertains to electrochromic polymers and polymer electrochromic devices. In a specific embodiment, two complementary polymers can be matched and incorporated into dual polymer electrochromic devices. The anodically coloring polymers in accordance with the subject invention can allow control over the color, brightness, and environmental stability of an electrochromic window. In addition, high device contrast ratios, high transmittance changes, and high luminance changes can be achieved, along with half-second switching times for full color change. Also provided are electrochromic devices such as advertising signage, video monitors, stadium scoreboards, computers, announcement boards, warning systems for cell phones, warning/information systems for automobiles, greeting cards, electrochromic windows, billboards, electronic books, and electrical wiring. The subject invention also provides for the use of complementary electrochromic polymers in the manufacture of electrochromic devices. In some embodiments, the devices of the invention can be prepared using metal vapor deposition or line patterning.