2,2'-(9-fluorenylidene)dipyridine | 856855-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,2'-(9-fluorenylidene)dipyridine
• 英文别名: 9,9-di-[2]pyridyl-fluorene；9,9-Di-[2]pyridyl-fluoren；2-(9-Pyridin-2-ylfluoren-9-yl)pyridine
• CAS: 856855-16-8
• 化学式: C₂₃H₁₆N₂
• 分子量: 320.393
• InChiKey: JTIJPZWIBFVCBH-UHFFFAOYSA-N

物化性质

• 熔点：
  213-214 °C
• 沸点：
  473.0±40.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2'-(9-fluorenylidene)dipyridine 在 双氧水 、 sodium methylate 、 sodium carbonate 、 氯化铵 、 苯甲酰氯 、 溶剂黄146 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 65.0h， 生成
  参考文献：
  名称：

  Pt(II) Metal Complexes Tailored with a Newly Designed Spiro-Arranged Tetradentate Ligand; Harnessing of Charge-Transfer Phosphorescence and Fabrication of Sky Blue and White OLEDs

  摘要：

  Tetradentate bis(pyridyl azolate) chelates are assembled by connecting two bidentate 3-trifluoromethyl-5-(2-pyridyl)azoles at the six position of pyridyl fragment with the tailored spiro-arranged fluorene and/or acridine functionalities. These new chelates were then utilized in synthesizing a series of Pt(II) metal complexes [Pt(Ln)], n = 1-5, from respective chelates L1-L5 and [PtCl2(DMSO)(2)] in 1,2-dimethoxyethane. The single-crystal X-ray structural analyses were executed on 1, 3, and 5 to reveal the generalized structures and packing arrangement in crystal lattices. Their photophysical properties were measured in both solution and solid state and are discussed in the context of computational analysis. These L1-L5 coordinated Pt(II) species exhibit intense emission, among which complex 5 shows remarkable solvatochromic phosphorescence due to the dominant intraligand charge transfer transition induced by the new bis(pyridyl azolate) chelates. Moreover, because of the higher-lying highest occupied molecular orbital of acridine, complex 5 can be considered as a novel bipolar phosphor. Successful fabrication of blue and white organic light-emitting diodes (OLEDs) using Pt(II) complexes 3 and 5 as the phosphorescent dopants are reported. In particular, blue OLEDs with 5 demonstrated peak efficiencies of 15.3% (36.3 cd/A, 38.0 lm/W), and CIE values of (0.190, 0.342) in a double-emitting layer structure. Furthermore, a red-emitting Os(II) complex and 5 were used to fabricate warm-white OLEDs to achieve peak external quantum efficiency, luminance efficiency, and power efficiency values as high as 12.7%, 22.5 cd/A, and 22.1 lm/W, respectively.

  DOI：

  10.1021/acs.inorgchem.5b00281
• 作为产物：
  描述：

  2-二吡啶基酮 在 盐酸 、 正丁基锂 、 乙酸酐 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 13.5h， 生成 2,2'-(9-fluorenylidene)dipyridine
  参考文献：
  名称：

  Pt(II) Metal Complexes Tailored with a Newly Designed Spiro-Arranged Tetradentate Ligand; Harnessing of Charge-Transfer Phosphorescence and Fabrication of Sky Blue and White OLEDs

  摘要：

  Tetradentate bis(pyridyl azolate) chelates are assembled by connecting two bidentate 3-trifluoromethyl-5-(2-pyridyl)azoles at the six position of pyridyl fragment with the tailored spiro-arranged fluorene and/or acridine functionalities. These new chelates were then utilized in synthesizing a series of Pt(II) metal complexes [Pt(Ln)], n = 1-5, from respective chelates L1-L5 and [PtCl2(DMSO)(2)] in 1,2-dimethoxyethane. The single-crystal X-ray structural analyses were executed on 1, 3, and 5 to reveal the generalized structures and packing arrangement in crystal lattices. Their photophysical properties were measured in both solution and solid state and are discussed in the context of computational analysis. These L1-L5 coordinated Pt(II) species exhibit intense emission, among which complex 5 shows remarkable solvatochromic phosphorescence due to the dominant intraligand charge transfer transition induced by the new bis(pyridyl azolate) chelates. Moreover, because of the higher-lying highest occupied molecular orbital of acridine, complex 5 can be considered as a novel bipolar phosphor. Successful fabrication of blue and white organic light-emitting diodes (OLEDs) using Pt(II) complexes 3 and 5 as the phosphorescent dopants are reported. In particular, blue OLEDs with 5 demonstrated peak efficiencies of 15.3% (36.3 cd/A, 38.0 lm/W), and CIE values of (0.190, 0.342) in a double-emitting layer structure. Furthermore, a red-emitting Os(II) complex and 5 were used to fabricate warm-white OLEDs to achieve peak external quantum efficiency, luminance efficiency, and power efficiency values as high as 12.7%, 22.5 cd/A, and 22.1 lm/W, respectively.

  DOI：

  10.1021/acs.inorgchem.5b00281

文献信息

• Über Alkylenimin-Derivate. II Mitteilung. Piperidin-Derivate mit zentralerregender Wirkung I
  作者：E. Sury、K. Hoffmann

  DOI：10.1002/hlca.19540370725

  日期：——

  A series of new piperidine derivatives substituted in the 2-position has been prepared and tested pharmacologically. Most of these compounds have central stimulating effects, above all the 2-diphenylmethyl-piperidine hydrochloride.

  已经制备并在药理学上测试了一系列在2-位取代的新哌啶衍生物。这些化合物大多数具有中心刺激作用，尤其是2-二苯基甲基-哌啶盐酸盐。
• AMINO FLUORENE POLYMER AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
  申请人：SAMSUNG ELECTRONICS CO., LTD.

  公开号：US20170062724A1

  公开（公告）日：2017-03-02

  An amino fluorene polymer including a first repeating unit represented by Formula 1: wherein, in Formula 1, A, F, F′, m1, n1, n2, R 1 , R 2 , R 3 , and R 4 are the same as described in the specification.

  一种氨基萘聚合物，包括由式1表示的第一重复单元：其中，在式1中，A、F、F′、m1、n1、n2、R1、R2、R3和R4与规范中描述的相同。
• Copolymer, organic light-emitting device material including the same, and organic light-emitting device including the organic light-emitting device material
  申请人：SAMSUNG ELECTRONICS CO., LTD.

  公开号：US10040887B2

  公开（公告）日：2018-08-07

  A copolymer including a unit represented by Formula 1 and a unit represented by Formula 2: wherein, in Formulae 1 and 2, groups and variables are the same as described in the specification.

  一种共聚物，包括式 1 所代表的单元和式 2 所代表的单元： 其中，式 1 和 2 中的基团和变量与说明书中所述相同。
• COPOLYMER, ORGANIC LIGHT-EMITTING DEVICE MATERIAL INCLUDING THE SAME, AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE ORGANIC LIGHT-EMITTING DEVICE MATERIAL
  申请人：SAMSUNG ELECTRONICS CO., LTD.

  公开号：US20170183439A1

  公开（公告）日：2017-06-29

  A copolymer including a unit represented by Formula 1 and a unit represented by Formula 2: wherein, in Formulae 1 and 2, groups and variables are the same as described in the specification.