4,9-bis{4-[2,2-bis(4-methoxyphenyl)-1-phenylvinyl]phenyl}[1,2,5]thiadiazolo-[3,4-g]quinoxaline | 1378502-48-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4,9-bis{4-[2,2-bis(4-methoxyphenyl)-1-phenylvinyl]phenyl}[1,2,5]thiadiazolo-[3,4-g]quinoxaline
• 英文别名: 4,9-Bis[4-[2,2-bis(4-methoxyphenyl)-1-phenylethenyl]phenyl]-[1,2,5]thiadiazolo[3,4-g]quinoxaline；4,9-bis[4-[2,2-bis(4-methoxyphenyl)-1-phenylethenyl]phenyl]-[1,2,5]thiadiazolo[3,4-g]quinoxaline
• CAS: 1378502-48-7
• 化学式: C₆₄H₄₈N₄O₄S
• 分子量: 969.176
• InChiKey: JZLPPJQOTLCLMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  73
• 可旋转键数：
  14
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,3-二羟基-1,4-二氧杂环己烷 、 4,7-bis(4-(2,2-bis(4-methoxyphenyl)-1-phenylvinyl)phenyl)benzo[c][1,2,5]thiadiazole-5,6-diamine 以 氯仿 、 溶剂黄146 为溶剂， 反应 24.0h， 以77%的产率得到4,9-bis{4-[2,2-bis(4-methoxyphenyl)-1-phenylvinyl]phenyl}[1,2,5]thiadiazolo-[3,4-g]quinoxaline
  参考文献：
  名称：

  Efficient Non-doped Near Infrared Organic Light-Emitting Devices Based on Fluorophores with Aggregation-Induced Emission Enhancement

  摘要：

  A family of donor-acceptor-donor (D-A-D) type near-infrared (NIR) fluorophores containing rigid nonplanar conjugated tetraphenylethene (TPE) moieties was designed and synthesized through Stifle coupling reactions with electron-deficient [1,2,5]thiadiazolo[3,4-g]quinoxaline (QTD) or benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole (BBTD) as acceptors. The absorption, fluorescence, and electrochemical properties were studied. These compounds exhibited good aggregation-induced emission enhancement (AIEE) property, as a result of the twisted TPE units, which restrict the intramolecular rotation and reduce the pi-pi stacking. Photoluminescence of these chromophores ranges from 600 to 1100 nm, and their HOMO-LUMO gaps are between 1.85 and 1.50 eV. Non-doped organic light-emitting diodes (OLEDs) based on these fluorophores were made and exhibited EL emission spectra peaking from 706 to 864 nm. The external quantum efficiency (EQE) of these devices ranged from 0.89% to 0.20% and remained fairly constant over a range of current density of 100-300 mA cm(-2). The device with the highest solid fluorescence efficiency emitter la shows the best performance with a maximum radiance of 2917 mW Sr-1 m(-2) and EQE of 0.89%. A contrast between nondoped and doped OLEDs with these materials confirms that AIEE compounds are suitable for fabricate efficient nondoped NIR OLEDs.

  DOI：

  10.1021/cm3008733

文献信息

• Efficient Non-doped Near Infrared Organic Light-Emitting Devices Based on Fluorophores with Aggregation-Induced Emission Enhancement
  作者：Xiaobo Du、Ji Qi、Zhiqiang Zhang、Dongge Ma、Zhi Y. Wang

  DOI：10.1021/cm3008733

  日期：2012.6.12

  A family of donor-acceptor-donor (D-A-D) type near-infrared (NIR) fluorophores containing rigid nonplanar conjugated tetraphenylethene (TPE) moieties was designed and synthesized through Stifle coupling reactions with electron-deficient [1,2,5]thiadiazolo[3,4-g]quinoxaline (QTD) or benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole (BBTD) as acceptors. The absorption, fluorescence, and electrochemical properties were studied. These compounds exhibited good aggregation-induced emission enhancement (AIEE) property, as a result of the twisted TPE units, which restrict the intramolecular rotation and reduce the pi-pi stacking. Photoluminescence of these chromophores ranges from 600 to 1100 nm, and their HOMO-LUMO gaps are between 1.85 and 1.50 eV. Non-doped organic light-emitting diodes (OLEDs) based on these fluorophores were made and exhibited EL emission spectra peaking from 706 to 864 nm. The external quantum efficiency (EQE) of these devices ranged from 0.89% to 0.20% and remained fairly constant over a range of current density of 100-300 mA cm(-2). The device with the highest solid fluorescence efficiency emitter la shows the best performance with a maximum radiance of 2917 mW Sr-1 m(-2) and EQE of 0.89%. A contrast between nondoped and doped OLEDs with these materials confirms that AIEE compounds are suitable for fabricate efficient nondoped NIR OLEDs.