1-(3,6-dibromo-9H-carbazol-9-yl)-5,5-dimethylhexane-2,4-dione | 1137672-34-4

• 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: 1-(3,6-dibromo-9H-carbazol-9-yl)-5,5-dimethylhexane-2,4-dione
• 英文别名: 1-(3,6-Dibromocarbazol-9-yl)-5,5-dimethylhexane-2,4-dione
• CAS: 1137672-34-4
• 化学式: C₂₀H₁₉Br₂NO₂
• 分子量: 465.184
• InChiKey: APDZICGEJUOKGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-正己基噻吩 、 1-(3,6-dibromo-9H-carbazol-9-yl)-5,5-dimethylhexane-2,4-dione 在 正丁基锂 、 三丁基氯化锡 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 13.0h， 以0.37 g的产率得到1-[3,6-Bis(5-hexylthiophen-2-yl)carbazol-9-yl]-5,5-dimethylhexane-2,4-dione
  参考文献：
  名称：

  Efficient Synthesis of Carbazolyl- and Thienyl-Substituted β-Diketonates and Properties of Their Red- and Green-Light-Emitting Ir(III) Complexes

  摘要：

  The efficient synthesis of novel beta-diketonates equipped with functional carbazolyl moieties and their subsequent transformations in 5-hexyl-thienyl substituted carbazole derivatives is presented by utilizing an effective Stille cross-coupling reaction. The introduced beta-diketonates served as ancillary ligands for novel heteroleptic red- and green-emitting Ir(III) complexes, when combined with 2-(naphthalen-1-yl)pyridine and 2-phenylpyridine as cyclometalating ligands. These novel Ir(III) complexes revealed color-tunability and a very good thermal stability until at least 207 degrees C. In polystyrene blends, the heteroleptic Ir(III) complexes revealed remarkable quantum yields up to 36% and suitably short phosphorescence lifetimes ranging from 1 to 4 mu s. In the case of the orange-red Ir(III) emitter, equipped with 2-(naphthalen-1-yl)pyridine cyclometallating ligands, a luminous efficiency as high as 7.7 cd/A at 7.4 V was achieved. All fabricated diodes exhibited in addition favorable color stability.

  DOI：

  10.1021/jo8025516
• 作为产物：
  描述：

  频哪酮 、 ethyl 2-(3,6-dibromo-9H-carbazol-9-yl)acetate 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 以67%的产率得到1-(3,6-dibromo-9H-carbazol-9-yl)-5,5-dimethylhexane-2,4-dione
  参考文献：
  名称：

  Efficient Synthesis of Carbazolyl- and Thienyl-Substituted β-Diketonates and Properties of Their Red- and Green-Light-Emitting Ir(III) Complexes

  摘要：

  The efficient synthesis of novel beta-diketonates equipped with functional carbazolyl moieties and their subsequent transformations in 5-hexyl-thienyl substituted carbazole derivatives is presented by utilizing an effective Stille cross-coupling reaction. The introduced beta-diketonates served as ancillary ligands for novel heteroleptic red- and green-emitting Ir(III) complexes, when combined with 2-(naphthalen-1-yl)pyridine and 2-phenylpyridine as cyclometalating ligands. These novel Ir(III) complexes revealed color-tunability and a very good thermal stability until at least 207 degrees C. In polystyrene blends, the heteroleptic Ir(III) complexes revealed remarkable quantum yields up to 36% and suitably short phosphorescence lifetimes ranging from 1 to 4 mu s. In the case of the orange-red Ir(III) emitter, equipped with 2-(naphthalen-1-yl)pyridine cyclometallating ligands, a luminous efficiency as high as 7.7 cd/A at 7.4 V was achieved. All fabricated diodes exhibited in addition favorable color stability.

  DOI：

  10.1021/jo8025516

文献信息

• Efficient Synthesis of Carbazolyl- and Thienyl-Substituted β-Diketonates and Properties of Their Red- and Green-Light-Emitting Ir(III) Complexes
  作者：Nan Tian、Alexander Thiessen、Ralf Schiewek、Oliver J. Schmitz、Dirk Hertel、Klaus Meerholz、Elisabeth Holder

  DOI：10.1021/jo8025516

  日期：2009.4.3

  The efficient synthesis of novel beta-diketonates equipped with functional carbazolyl moieties and their subsequent transformations in 5-hexyl-thienyl substituted carbazole derivatives is presented by utilizing an effective Stille cross-coupling reaction. The introduced beta-diketonates served as ancillary ligands for novel heteroleptic red- and green-emitting Ir(III) complexes, when combined with 2-(naphthalen-1-yl)pyridine and 2-phenylpyridine as cyclometalating ligands. These novel Ir(III) complexes revealed color-tunability and a very good thermal stability until at least 207 degrees C. In polystyrene blends, the heteroleptic Ir(III) complexes revealed remarkable quantum yields up to 36% and suitably short phosphorescence lifetimes ranging from 1 to 4 mu s. In the case of the orange-red Ir(III) emitter, equipped with 2-(naphthalen-1-yl)pyridine cyclometallating ligands, a luminous efficiency as high as 7.7 cd/A at 7.4 V was achieved. All fabricated diodes exhibited in addition favorable color stability.