bis(3-(acryloyloxy)propyl)-[2,2'-bipyridine]-4,4'-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: bis(3-(acryloyloxy)propyl)-[2,2'-bipyridine]-4,4'-dicarboxylate
• 英文别名: 3-Prop-2-enoyloxypropyl 2-[4-(3-prop-2-enoyloxypropoxycarbonyl)pyridin-2-yl]pyridine-4-carboxylate；3-prop-2-enoyloxypropyl 2-[4-(3-prop-2-enoyloxypropoxycarbonyl)pyridin-2-yl]pyridine-4-carboxylate
• 化学式: C₂₄H₂₄N₂O₈
• 分子量: 468.463
• InChiKey: WWPMVORKJXIWRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 顺-双(2,2-二吡啶)二氯化钌(II) 水合物 、 bis(3-(acryloyloxy)propyl)-[2,2'-bipyridine]-4,4'-dicarboxylate 在 HOC₆H₂(C(CH₃)3)2CH₃ 作用下， 以 乙二醇 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  Establishing Dual Electrogenerated Chemiluminescence and Multicolor Electrochromism in Functional Ionic Transition-Metal Complexes

  摘要：

  A combination of electrochromism and electroluminescence in functional materials could lead to single-layer dual electrochromic/electroluminescent (EC/EL) display devices, capable of simultaneous operation in emissive and reflective modes. Whereas such next generation displays could provide optimal visibility in any ambient lighting situation, materials available that exhibit such characteristics in the active layer are limited due to the required intrinsic multifunctionality (i.e., redox activity, electroluminescence, electrochromism, and ion conductivity) and to date can only be achieved via the rational design of ionic transition-metal I complexes. Reported herein is the synthesis and characterization of a new family of acrylate-containing ruthenium (tris)bipyridine-based coordination complexes with multifunctional characteristics. Potential use of the presented compounds in EC/EL devices is established, as they are applied as cross-linked electrochromic films and electrochemiluminescent layers in light-emitting electrochemical cell devices. Electrochromic switching of the polymeric networks between yellow, orange, green, brown and transmissive states is demonstrated, and electrochemiluminescent devices based on the complexes synthesized show red-orange to deep red emission with lambda(max) ranging from 680 to 722 nm and luminance up to 135 cd/m(2). Additionally, a dual EC/EL device prototype is presented where light emission and multicolor electrochromism occur from the same pixel comprised of a single active layer, demonstrating a true combination of these properties in ionic transition-metal complexes.

  DOI：

  10.1021/ja2065297
• 作为产物：
  描述：

  2,2'-联吡啶-4,4'-二甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 46.0h， 生成 bis(3-(acryloyloxy)propyl)-[2,2'-bipyridine]-4,4'-dicarboxylate
  参考文献：
  名称：

  Establishing Dual Electrogenerated Chemiluminescence and Multicolor Electrochromism in Functional Ionic Transition-Metal Complexes

  摘要：

  A combination of electrochromism and electroluminescence in functional materials could lead to single-layer dual electrochromic/electroluminescent (EC/EL) display devices, capable of simultaneous operation in emissive and reflective modes. Whereas such next generation displays could provide optimal visibility in any ambient lighting situation, materials available that exhibit such characteristics in the active layer are limited due to the required intrinsic multifunctionality (i.e., redox activity, electroluminescence, electrochromism, and ion conductivity) and to date can only be achieved via the rational design of ionic transition-metal I complexes. Reported herein is the synthesis and characterization of a new family of acrylate-containing ruthenium (tris)bipyridine-based coordination complexes with multifunctional characteristics. Potential use of the presented compounds in EC/EL devices is established, as they are applied as cross-linked electrochromic films and electrochemiluminescent layers in light-emitting electrochemical cell devices. Electrochromic switching of the polymeric networks between yellow, orange, green, brown and transmissive states is demonstrated, and electrochemiluminescent devices based on the complexes synthesized show red-orange to deep red emission with lambda(max) ranging from 680 to 722 nm and luminance up to 135 cd/m(2). Additionally, a dual EC/EL device prototype is presented where light emission and multicolor electrochromism occur from the same pixel comprised of a single active layer, demonstrating a true combination of these properties in ionic transition-metal complexes.

  DOI：

  10.1021/ja2065297

文献信息

• Highly Efficient Solid-State Electrochemically Generated Chemiluminescence from Ester-Substituted Trisbipyridineruthenium(II)-Based Polymers
  作者：C. Michael Elliott、François Pichot、Corey J. Bloom、Lonn S. Rider

  DOI：10.1021/ja974347m

  日期：1998.6.13

  A polymerizable ester-substituted trisbipyridine complex of ruthenium(II) has been synthesized and the solid-state electrochemiluminescence (ECL) properties of its, polymer evaluated. A collection of 12 "sandwich-type" solid-state cells were investigated each having a similar to 0.3 mu m thick film of the polymer sandwiched between a transparent indium/tin oxide (ITO) anode and a porous Au cathode. The ECL of these devices was evaluated in the solid state. Despite considerable variability in performance, the most efficient of these devices exhibited ECL quantum yields matching the efficiency of the best organic polymer based light-emitting devices.
• Establishing Dual Electrogenerated Chemiluminescence and Multicolor Electrochromism in Functional Ionic Transition-Metal Complexes
  作者：Egle Puodziukynaite、Justin L. Oberst、Aubrey L. Dyer、John R. Reynolds

  DOI：10.1021/ja2065297

  日期：2012.1.18

  A combination of electrochromism and electroluminescence in functional materials could lead to single-layer dual electrochromic/electroluminescent (EC/EL) display devices, capable of simultaneous operation in emissive and reflective modes. Whereas such next generation displays could provide optimal visibility in any ambient lighting situation, materials available that exhibit such characteristics in the active layer are limited due to the required intrinsic multifunctionality (i.e., redox activity, electroluminescence, electrochromism, and ion conductivity) and to date can only be achieved via the rational design of ionic transition-metal I complexes. Reported herein is the synthesis and characterization of a new family of acrylate-containing ruthenium (tris)bipyridine-based coordination complexes with multifunctional characteristics. Potential use of the presented compounds in EC/EL devices is established, as they are applied as cross-linked electrochromic films and electrochemiluminescent layers in light-emitting electrochemical cell devices. Electrochromic switching of the polymeric networks between yellow, orange, green, brown and transmissive states is demonstrated, and electrochemiluminescent devices based on the complexes synthesized show red-orange to deep red emission with lambda(max) ranging from 680 to 722 nm and luminance up to 135 cd/m(2). Additionally, a dual EC/EL device prototype is presented where light emission and multicolor electrochromism occur from the same pixel comprised of a single active layer, demonstrating a true combination of these properties in ionic transition-metal complexes.