bis(6-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)methanone | 950904-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: bis(6-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)methanone
• 英文别名: Bis[6-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]methanone；bis[6-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]methanone
• CAS: 950904-45-7
• 化学式: C₁₉H₂₀N₂O₅
• 分子量: 356.378
• InChiKey: MDOKRZOQMRXWSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  bis(6-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)methanone 在 盐酸 、 正丁基锂 、 乙酸酐 、 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， 反应 49.5h， 生成 10-phenyl-9,9-bis(6-(3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridin-2-yl)-9,10-dihydroacridine
  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：

  2,6-二溴吡啶 在 正丁基锂 、 水 、 叔丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 25.5h， 生成 bis(6-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)methanone
  参考文献：
  名称：

  A Family of Immobilizable Chiral Bis(pinenebipyridine) Ligands

  摘要：

  New enantiopure ligands containing two (-)-5,6-pinenebipyridine units connected by a bridge situated in position 6 of the bipyridines have been prepared. The chemically addressable groups of the bridging (hydroxyl or keto) can be covalently bound to various supports in order to heterogenize the ligand.

  DOI：

  10.1055/s-0033-1339847

文献信息

• 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
  作者：Kuan-Yu Liao、Che-Wei Hsu、Yun Chi、Ming-Kuan Hsu、Szu-Wei Wu、Chih-Hao Chang、Shih-Hung Liu、Gene-Hsiang Lee、Pi-Tai Chou、Yue Hu、Neil Robertson

  DOI：10.1021/acs.inorgchem.5b00281

  日期：2015.4.20

  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.
• A Family of Immobilizable Chiral Bis(pinenebipyridine) Ligands
  作者：Olimpia Mamula、Alpár Pöllnitz、Radek Skupienski、Helen Stoeckli-Evans、Aurélien Crochet、Anca Silvestru、Katharina Fromm

  DOI：10.1055/s-0033-1339847

  日期：——

  New enantiopure ligands containing two (-)-5,6-pinenebipyridine units connected by a bridge situated in position 6 of the bipyridines have been prepared. The chemically addressable groups of the bridging (hydroxyl or keto) can be covalently bound to various supports in order to heterogenize the ligand.