3-(5-bromothiophen-2-yl)-7-(dodecyloxy)coumarin | 1616862-70-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(5-bromothiophen-2-yl)-7-(dodecyloxy)coumarin
• 英文别名: 3-(5-Bromothiophen-2-yl)-7-dodecoxychromen-2-one；3-(5-bromothiophen-2-yl)-7-dodecoxychromen-2-one
• CAS: 1616862-70-4
• 化学式: C₂₅H₃₁BrO₃S
• 分子量: 491.489
• InChiKey: ZZVZFGSPOPRBMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(5-bromothiophen-2-yl)-7-(dodecyloxy)coumarin 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 20.5h， 生成 3-(5'-bromo-2,2'-bithiophen-5-yl)-7-(dodecyloxy)coumarin
  参考文献：
  名称：

  Synthesis and characterization of carbazole dendronized coumarin derivatives as solution-processed non-doped emitters and hole-transporters for electroluminescent devices

  摘要：

  合成并表征了一系列含有寡聚噻吩香豆素作为核心和高达第三代的咔唑树 dendron 作为取代基的咔唑 dendron 化香豆素衍生物 (CTmGn，m = 0–2，n = 1–3)。研究了它们作为非掺杂溶液加工光发射体和 OLED 用孔传输体的光学、热、 electrochemical 和电致发光性质。它们表现出明亮的淡蓝色至黄色荧光，溶液荧光量子产率 (ΦF) 大约为 0.10–0.40，并具有高达 285 °C 的高玻璃转变温度的形态稳定的非晶薄膜。作为发光层，结构为 ITO/PEDOT:PSS/CTmGn/BCP/LiF:Al 的溶液加工 OLED 发出淡蓝色至黄色的光，最大亮度效率高达 7.92 cd A−1，开启电压低至 3.6 V。作为孔传输层，结构为 ITO/PEDOT:PSS/CGn/Alq3/LiF:Al 的溶液加工 OLED 显示明亮的绿色发射 (λEL = 518 nm, CIE = 0.27, 0.53)，最大亮度效率高达 6.54 cd A−1，开启电压低至 2.5 V。

  DOI：

  10.1039/c4nj00602j
• 作为产物：
  描述：

  3-(thiophen-2-yl)-7-(dodecyloxy)coumarin 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到3-(5-bromothiophen-2-yl)-7-(dodecyloxy)coumarin
  参考文献：
  名称：

  Synthesis and characterization of carbazole dendronized coumarin derivatives as solution-processed non-doped emitters and hole-transporters for electroluminescent devices

  摘要：

  合成并表征了一系列含有寡聚噻吩香豆素作为核心和高达第三代的咔唑树 dendron 作为取代基的咔唑 dendron 化香豆素衍生物 (CTmGn，m = 0–2，n = 1–3)。研究了它们作为非掺杂溶液加工光发射体和 OLED 用孔传输体的光学、热、 electrochemical 和电致发光性质。它们表现出明亮的淡蓝色至黄色荧光，溶液荧光量子产率 (ΦF) 大约为 0.10–0.40，并具有高达 285 °C 的高玻璃转变温度的形态稳定的非晶薄膜。作为发光层，结构为 ITO/PEDOT:PSS/CTmGn/BCP/LiF:Al 的溶液加工 OLED 发出淡蓝色至黄色的光，最大亮度效率高达 7.92 cd A−1，开启电压低至 3.6 V。作为孔传输层，结构为 ITO/PEDOT:PSS/CGn/Alq3/LiF:Al 的溶液加工 OLED 显示明亮的绿色发射 (λEL = 518 nm, CIE = 0.27, 0.53)，最大亮度效率高达 6.54 cd A−1，开启电压低至 2.5 V。

  DOI：

  10.1039/c4nj00602j

文献信息

• Coumarin-cored carbazole dendrimers as solution-processed non-doped green emitters for electroluminescent devices
  作者：Narid Prachumrak、Sirintra Potjanasopa、Rattanawalee Rattanawan、Supawadee Namuangruk、Siriporn Jungsuttiwong、Tinnagon Keawin、Taweesak Sudyoadsuk、Vinich Promarak

  DOI：10.1016/j.tet.2014.03.088

  日期：2014.9

  A series of green-emitting thiophenyl coumarin-cored carbazole dendrimers containing carbazole dendrons up to the third generation as substituent were synthesized and characterization. Their optical, thermal, electrochemical, and electroluminescent properties as non-doped solution-processed light-emitters for OLEDs were investigated. By incorporating carbazole dendrons in the molecule, we are able to reduce the crystallization and retain the high emissive ability of a planar thiophenyl coumarin fluorescent core in the solid state as well as improve the thermal stability of the material. These dendrimers showed a bright-green fluorescence and can form morphologically stable amorphous thin films with glass-transition temperatures as high as 285 degrees C. Simple structured solution-processed OLEDs using these materials as hole-transporting non-doped emitters and BCP as a buffer layer emit a stable green electroluminescence (lambda(EL)=502-526 nm) with high luminance efficiencies (up to 7.92 cd/A at 7.39 mA/cm(2)) and high green color purity (CIE=0.26, 0.62, which are close to the pure green color). (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and characterization of carbazole dendronized coumarin derivatives as solution-processed non-doped emitters and hole-transporters for electroluminescent devices
  作者：Narid Prachumrak、Sirintra Pojanasopa、Ruangchai Tarsang、Supawadee Namuangruk、Siriporn Jungsuttiwong、Tinnagon Keawin、Taweesak Sudyoadsuk、Vinich Promarak

  DOI：10.1039/c4nj00602j

  日期：——

  A series of carbazole dendronized coumarin derivatives (CTmGn, m = 0–2, n = 1–3) containing oligothiophenyl coumarins as cores and carbazole dendrons up to the third generation as substituents were synthesized and characterized. Their optical, thermal, electrochemical, and electroluminescent properties as non-doped solution-processed light-emitters and hole-transporters for OLEDs were investigated. They exhibited a bright light blue to yellow fluorescence with solution fluorescence quantum yields (ΦF) of about 0.10–0.40 and morphologically stable amorphous thin films with glass transition temperatures as high as 285 °C. As emissive layers, solution-processed OLEDs with the structure of ITO/PEDOT:PSS/CTmGn/BCP/LiF:Al emitted light blue to yellow colours with a maximum luminance efficiency as high as 7.92 cd A−1 and a low turn-on voltage of 3.6 V. As hole-transporting layers, solution-processed OLEDs with the structure of ITO/PEDOT:PSS/CGn/Alq3/LiF:Al showed a bright green emission (λEL = 518 nm, CIE = 0.27, 0.53) with a maximum luminance efficiency as high as 6.54 cd A−1 and a low turn-on voltage of 2.5 V.

  合成并表征了一系列含有寡聚噻吩香豆素作为核心和高达第三代的咔唑树 dendron 作为取代基的咔唑 dendron 化香豆素衍生物 (CTmGn，m = 0–2，n = 1–3)。研究了它们作为非掺杂溶液加工光发射体和 OLED 用孔传输体的光学、热、 electrochemical 和电致发光性质。它们表现出明亮的淡蓝色至黄色荧光，溶液荧光量子产率 (ΦF) 大约为 0.10–0.40，并具有高达 285 °C 的高玻璃转变温度的形态稳定的非晶薄膜。作为发光层，结构为 ITO/PEDOT:PSS/CTmGn/BCP/LiF:Al 的溶液加工 OLED 发出淡蓝色至黄色的光，最大亮度效率高达 7.92 cd A−1，开启电压低至 3.6 V。作为孔传输层，结构为 ITO/PEDOT:PSS/CGn/Alq3/LiF:Al 的溶液加工 OLED 显示明亮的绿色发射 (λEL = 518 nm, CIE = 0.27, 0.53)，最大亮度效率高达 6.54 cd A−1，开启电压低至 2.5 V。