6-(6'-(2'',7''-di-bromo-9''-octylfluoren-9''-yl)hexyloxy)picolinic acid | 1217890-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(6'-(2'',7''-di-bromo-9''-octylfluoren-9''-yl)hexyloxy)picolinic acid
• 英文别名: 6-(6-(2,7-dibromo-9-octyl-9H-fluoren-9-yl)hexyloxy)picolinic acid；6-[6-(2,7-Dibromo-9-octylfluoren-9-yl)hexoxy]pyridine-2-carboxylic acid；6-[6-(2,7-dibromo-9-octylfluoren-9-yl)hexoxy]pyridine-2-carboxylic acid
• CAS: 1217890-45-3
• 化学式: C₃₃H₃₉Br₂NO₃
• 分子量: 657.486
• InChiKey: DSCRQJGCIHUKMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(6'-(2'',7''-di-bromo-9''-octylfluoren-9''-yl)hexyloxy)picolinic acid 、 [(2-(4-tert-butylphenyl)pyridine)₂IrCl]₂ 在 sodium carbonate 作用下， 以 乙二醇乙醚 为溶剂， 反应 15.0h， 以63.2%的产率得到
  参考文献：
  名称：

  Novel iridium complexes containing alkylfluorene functionalized picolinic acid ancillary ligand: Synthesis, optophysics and electroluminescence properties

  摘要：

  Two novel green-emitting cyclometalated iridium complexes of (Buppy)(2)Ir(Tfl-pic) and (Buppy)(2)Ir(Brfl-pic) were synthesized and characterized, in which Buppy is 2-(4-tert-butylphenyl) pyridine, Tfl-pic is 6-(6'-(9 ''-octyl-2 '',7 ''-bi(9,9-dioctylfluoren-2-yl)fluoren-9 ''-yl)hexyloxy) picolinic acid and Brfl is 6-(6'-(2 '',7 ''-di-bromo-9 ''-octylfluoren-9 ''-yl)hexyloxy) picolinic acid. Their thermal property, dispersibility and optophysical properties were investigated. Both iridium complexes present intense UV absorption bands and photoluminescence performance in CH2Cl2. Single-emissive-layer polymer light-emitting devices using (Buppy)(2)Ir(Tfl-pic) and (Buppy)(2)Ir(Brfl-pic) as a single dopant and a blend of poly(vinylcarbazole) and 2-(4-biphenyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole as the host matrix were fabricated. The (Buppy)(2)Ir(Tfl-pic)-doped devices exhibited a maximum current efficiency of 2.44 cd A(-1). As expected, the phase separation and concentration quenching of these iridium complexes in the devices are efficiently suppressed due to appending bulky fluorene derivatives on the picolinic acid unit by a non-conjugated connection. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.03.015
• 作为产物：
  描述：

  methyl 6-(6-(2,7-dibromo-9-octyl-9H-fluoren-9-yl)hexyloxy)picolinate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以91.8%的产率得到6-(6'-(2'',7''-di-bromo-9''-octylfluoren-9''-yl)hexyloxy)picolinic acid
  参考文献：
  名称：

  Synthesis, opto-physics, and electroluminescence of cyclometalated iridium (III) complex with alkyltrifluorene picolinic acid

  摘要：

  To improve the opto-physics, electroluminescence, and dispersibility of iridium (III) complexes in polymer light-emitting devices, we synthesized and characterized two red-emitting heteroleptic cyclometalated iridium (III) complexes of (Piq)(2)Ir(Tfl-pic) and (Piq)(2)Ir(Brfl-pic), in which Piq is 1-phenylisoquinoline, Tfl-pic and Brfl-pic are alkyltrifluorene- and dibromoalkylfluorene-containing picolinic acid derivatives bridged with alkoxy chain, respectively. Compared to (Piq)(2)Ir(pic) and (Piq)(2)Ir(Brfl-pic), (Piq)(2)Ir(Tfl-pic) exhibited higher thermal stability, better dispersibility and excellent quantum efficiency. High-efficiency red emission with a maximum current efficiency of 6.28 cdA(-1) and a maximum EL peak at 608 nm was obtained in the (Piq)(2)Ir(Tfl-pic)-doped devices using a blend of poly(9,9-dioctylfluorene) and 2-(4-biphenyl)-5-(4-tert -butylphenyl)-1,3,4-oxadiazole as a host matrix. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.12.001

文献信息

• Synthesis, opto-physics, and electroluminescence of cyclometalated iridium (III) complex with alkyltrifluorene picolinic acid
  作者：Yafei Wang、Hua Tan、Yu Liu、Chenxian Jiang、Zhengyong Hu、Meixiang Zhu、Lei Wang、Weiguo Zhu、Yong Cao

  DOI：10.1016/j.tet.2009.12.001

  日期：2010.2

  To improve the opto-physics, electroluminescence, and dispersibility of iridium (III) complexes in polymer light-emitting devices, we synthesized and characterized two red-emitting heteroleptic cyclometalated iridium (III) complexes of (Piq)(2)Ir(Tfl-pic) and (Piq)(2)Ir(Brfl-pic), in which Piq is 1-phenylisoquinoline, Tfl-pic and Brfl-pic are alkyltrifluorene- and dibromoalkylfluorene-containing picolinic acid derivatives bridged with alkoxy chain, respectively. Compared to (Piq)(2)Ir(pic) and (Piq)(2)Ir(Brfl-pic), (Piq)(2)Ir(Tfl-pic) exhibited higher thermal stability, better dispersibility and excellent quantum efficiency. High-efficiency red emission with a maximum current efficiency of 6.28 cdA(-1) and a maximum EL peak at 608 nm was obtained in the (Piq)(2)Ir(Tfl-pic)-doped devices using a blend of poly(9,9-dioctylfluorene) and 2-(4-biphenyl)-5-(4-tert -butylphenyl)-1,3,4-oxadiazole as a host matrix. (C) 2009 Elsevier Ltd. All rights reserved.
• Novel iridium complexes containing alkylfluorene functionalized picolinic acid ancillary ligand: Synthesis, optophysics and electroluminescence properties
  作者：Junting Yu、Yafei Wang、Yu Liu、Xianping Deng、Hua Tan、Zhiyong Zhang、Meixiang Zhu、Weiguo Zhu

  DOI：10.1016/j.jorganchem.2014.03.015

  日期：2014.7

  Two novel green-emitting cyclometalated iridium complexes of (Buppy)(2)Ir(Tfl-pic) and (Buppy)(2)Ir(Brfl-pic) were synthesized and characterized, in which Buppy is 2-(4-tert-butylphenyl) pyridine, Tfl-pic is 6-(6'-(9 ''-octyl-2 '',7 ''-bi(9,9-dioctylfluoren-2-yl)fluoren-9 ''-yl)hexyloxy) picolinic acid and Brfl is 6-(6'-(2 '',7 ''-di-bromo-9 ''-octylfluoren-9 ''-yl)hexyloxy) picolinic acid. Their thermal property, dispersibility and optophysical properties were investigated. Both iridium complexes present intense UV absorption bands and photoluminescence performance in CH2Cl2. Single-emissive-layer polymer light-emitting devices using (Buppy)(2)Ir(Tfl-pic) and (Buppy)(2)Ir(Brfl-pic) as a single dopant and a blend of poly(vinylcarbazole) and 2-(4-biphenyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole as the host matrix were fabricated. The (Buppy)(2)Ir(Tfl-pic)-doped devices exhibited a maximum current efficiency of 2.44 cd A(-1). As expected, the phase separation and concentration quenching of these iridium complexes in the devices are efficiently suppressed due to appending bulky fluorene derivatives on the picolinic acid unit by a non-conjugated connection. (C) 2014 Elsevier B.V. All rights reserved.