2-((5-methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridine | 1216265-72-3

• 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: 2-((5-methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridine
• 英文别名: 2-(5-(methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridine；trzl-CH2OMe；2-[3-(methoxymethyl)-1H-1,2,4-triazol-5-yl]pyridine；2-[5-(methoxymethyl)-1H-1,2,4-triazol-3-yl]pyridine
• CAS: 1216265-72-3
• 化学式: C₉H₁₀N₄O
• mdl: MFCD13704060
• 分子量: 190.205
• InChiKey: OFHDUUSEBZMLNT-UHFFFAOYSA-N

物化性质

• 沸点：
  404.9±51.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iridium(III) acetylacetonate 、 2-((5-methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridine 以 乙二醇 为溶剂， 反应 24.0h， 以29%的产率得到tris-(2-(5-(methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridinato)iridium
  参考文献：
  名称：

  The Blue Phosphorescent Iridium Complexes Containing the Pyridyltriazole Derivatives as a Main Ligand

  摘要：

  The titled iridium compounds involving the electron-withdrawing pyridyltriazole derivative as a main ligand were synthesized. The main ligand, 2-(5-methoxy-methyl)-2-H1,2,4-triazol-3-yl)pyridine (trzl-CH2OMe), was designed for development of the blue light-emitting iridium complexes. The ligand involves the electron-withdrawing moiety, N, which may contribute to lowering the HOMO energy level of the complex. In this paper, the new homoleptic complex, tris-(2-(5-(methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridinato)iridium (Ir(trzl-CH2OMe)(3)), was synthesized with trzl-CH2OMe as the main ligand. The heteroleptic complexes containing trzl-CH2OMe and other ancillary ligands were also prepared, where the ancillary ligands, acac and pic, represent acetylacetonate and picolinate, respectively. The photophysical properties of the iridium complexes prepared herein, Ir(trzl-CH2OMe) (3), Ir(trzl-CH2OMe)(2)(acac), Ir(trzl-CH2OMe)(2)(pic) were investigated. Their photoluminescence maximum appeared at 445 nm, 460 nm and 472 nm, respectively. We also investigated the electrochemical properties of these iridium complexes for the possible application to organic light-emitting diodes.

  DOI：

  10.1080/15421406.2012.703439
• 作为产物：
  描述：

  2-氰基吡啶 在 sodium carbonate 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 生成 2-((5-methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridine
  参考文献：
  名称：

  The Blue Phosphorescent Iridium Complexes Containing New Triazole Ligands for OLEDs

  摘要：

  For the application to organic light-emitting diodes (OLEDs), the blue light emitting iridium complexes containing a new triazole (trzl) ancillary ligand were prepared and their photophysical properties was studied with respect to substituent effect at the 5-position of the triazole in the complexes. As substituents, electron donating groups, CMe3 and CH2OMe were introduced to the triazole ligand of the complex to investigate the electronic effect on their chromacity and efficiency. The absorption patterns of the iridium complexes, Ir(F-2-ppy)(2)(trzl-CMe3) and Ir(F-2-ppy)(2)(trzl-CH2OMe) prepared in this study were very similar. Their PL spectra exhibited the blue emission at 464 and 462 nm with the shoulder at 490 nm, respectively. Previously reported Ir(F-2-ppy)(2)(trzl-Me) showed almost identical emission maxima at 461 nm with a shoulder at 492 nm. Such similar emission patterns of these complexes indicate that the ancillary ligands, derivatives of triazole, did not make significant influence on chromaticity of their iridium complexes.

  DOI：

  10.1080/15421400902939504

文献信息

• Pyridyltriazole as a Main Ligand in the Iridium Complexes for Blue Phosphorescence
  作者：So Youn Ahn、Yunkyoung Ha

  DOI：10.1080/15421401003609251

  日期：2010.4.13

  New blue-phosphorescent iridium complexes containing pyridyltriazole derivatives (trzl-CH2OMe) as main ligands and benzyldiphenylphosphines (bdp) as ancillary ligands were synthesized and their photophysical properties were investigated. As a main ligand, 2-(5-(methoxymethyl)-2H-1,2,4-triazol-3-yl) pyridine (trzl-CH2OMe), which has the strong electron-withdrawing ability was chosen to give the deep blue emission of its iridium complexes. As ancillary ligands, bdp and bdp-F-2, were employed where they represents benzyldiphenylphosphine and (3,5-difluorobenzyl)-diphenylphosphine, respectively. The resulting iridium complexes, Ir(trzl-CH2OMe)(2)(bdp) and Ir(trzl-CH2OMe)(2)(bdp-F-2), exhibited the blue emission at 484 and 481 nm in CH2Cl2 solution, respectively. These emission was blue shifted, compared to that of the previously reported Ir complex containing a fluorinated phenylpyridine and bdp, Ir(4-Me-4'-F-ppy)(2)(bdp) at 491 nm. We also investigated the solid state luminescence properties of the complexes prepared herein in a polymer film of PMMA (poly(methylmetacrylate)) for their application to the polymeric process.
• The Blue Phosphorescent Iridium Complexes Containing New Triazole Ligands for OLEDs
  作者：So Youn Ahn、Yunkyoung Ha

  DOI：10.1080/15421400902939504

  日期：2009.6.18

  For the application to organic light-emitting diodes (OLEDs), the blue light emitting iridium complexes containing a new triazole (trzl) ancillary ligand were prepared and their photophysical properties was studied with respect to substituent effect at the 5-position of the triazole in the complexes. As substituents, electron donating groups, CMe3 and CH2OMe were introduced to the triazole ligand of the complex to investigate the electronic effect on their chromacity and efficiency. The absorption patterns of the iridium complexes, Ir(F-2-ppy)(2)(trzl-CMe3) and Ir(F-2-ppy)(2)(trzl-CH2OMe) prepared in this study were very similar. Their PL spectra exhibited the blue emission at 464 and 462 nm with the shoulder at 490 nm, respectively. Previously reported Ir(F-2-ppy)(2)(trzl-Me) showed almost identical emission maxima at 461 nm with a shoulder at 492 nm. Such similar emission patterns of these complexes indicate that the ancillary ligands, derivatives of triazole, did not make significant influence on chromaticity of their iridium complexes.
• The Blue Phosphorescent Iridium Complexes Containing the Pyridyltriazole Derivatives as a Main Ligand
  作者：Hye Rim Park、Ye Young Yi、Yunkyoung Ha

  DOI：10.1080/15421406.2012.703439

  日期：2012.11.15

  The titled iridium compounds involving the electron-withdrawing pyridyltriazole derivative as a main ligand were synthesized. The main ligand, 2-(5-methoxy-methyl)-2-H1,2,4-triazol-3-yl)pyridine (trzl-CH2OMe), was designed for development of the blue light-emitting iridium complexes. The ligand involves the electron-withdrawing moiety, N, which may contribute to lowering the HOMO energy level of the complex. In this paper, the new homoleptic complex, tris-(2-(5-(methoxymethyl)-2H-1,2,4-triazol-3-yl)pyridinato)iridium (Ir(trzl-CH2OMe)(3)), was synthesized with trzl-CH2OMe as the main ligand. The heteroleptic complexes containing trzl-CH2OMe and other ancillary ligands were also prepared, where the ancillary ligands, acac and pic, represent acetylacetonate and picolinate, respectively. The photophysical properties of the iridium complexes prepared herein, Ir(trzl-CH2OMe) (3), Ir(trzl-CH2OMe)(2)(acac), Ir(trzl-CH2OMe)(2)(pic) were investigated. Their photoluminescence maximum appeared at 445 nm, 460 nm and 472 nm, respectively. We also investigated the electrochemical properties of these iridium complexes for the possible application to organic light-emitting diodes.