1,5-dimethyl-2,4-bis(3-methylpyrazolyl)benzene | 949097-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-dimethyl-2,4-bis(3-methylpyrazolyl)benzene
• 英文别名: dmbpzb；1-[2,4-Dimethyl-5-(3-methylpyrazol-1-yl)phenyl]-3-methylpyrazole
• CAS: 949097-28-3
• 化学式: C₁₆H₁₈N₄
• 分子量: 266.346
• InChiKey: SBCIMEUMBFRZFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯化铱(III) 水合物 、 1,5-dimethyl-2,4-bis(3-methylpyrazolyl)benzene 以 甲醇 为溶剂， 以39%的产率得到[Ir(1,5-dimethyl-2,4-bis(3-methylpyrazolyl)benzene(-1H))Cl2]2
  参考文献：
  名称：

  Syntheses and Phosphorescent Properties of Blue Emissive Iridium Complexes with Tridentate Pyrazolyl Ligands

  摘要：

  Novel neutral mixed-ligand lr(N boolean AND C boolean AND N)(N boolean AND C)X complexes (N boolean AND C boolean AND N = 1, 3-bis (3-methylpyrazolyl)benzene (bpzb), 1,5-dimethyl-2,4-bis(3-methylpyrazolyl)benzene (dmbpzb), and 1,5-difluoro-2,4-bis(3-methylpyrazolyl)benzene (dfbpzb); N boolean AND C = 2-phenyl pyridine (ppy); and X = Cl or CN) have been synthesized and characterized. An X-ray single-crystal structure of the complex lr(dmbpzb)(ppy)Cl shows that the nitrogen atom in the ppy ligand occupied the trans position to the carbon atom in the tridentate N boolean AND C boolean AND N ligand of dmbpzb with the lr-C bond length of 1.94(1) angstrom, whereas the coordinating carbon atom occupied the trans position of chlorine. Electrochemical data show that the complexes exhibit an oxidation lr(III/IV) process in the potential range of +0.5 similar to 0.9 V and two irreversible reductions at approximately -2.6 and -3.0 V against Fc(0)/Fc(+), respectively. All of the lr(III) complexes do not emit phosphorescence at room temperature, although strong phosphorescence is exhibited at 77 K with the 0-0 transition centered at around 450 nm and lifetimes of 3-14 mu s. DFT calculations indicate that the HOMOs are mainly localized on iridium 5d pi and chlorine p pi*, whereas the LUMOs are mainly from the ppy ligand pi* orbitals. The phosphorescence originates from a (LC)-L-3 state mixed with the (MLCT)-M-3 and (XLCT)-X-3 ones. Temperature-dependent lifetime measurements of lr(dfbpzb)(ppy)Cl reveal the existence of a thermal deactivation process with a low activation energy (1720 cm(-1)) and very high frequency factor (2.3 x 10(13) s(-1)). An unrestricted density functional theory indicates that the dd state, in which both the lr-N (pyrazolyl) bond lengths increase considerably, exists almost at the same energy as that for the phosphorescent state. A thorough analysis based on the potential energy surfaces for the T-1 and S-0 states allows us to determine the reaction pathway responsible for this thermal deactivation. The calculated activation energies of 1600 similar to 1800 cm(-1) are in excellent agreement with the observed values.

  DOI：

  10.1021/ic800196s

文献信息

• EP1992631A1
  申请人：——

  公开号：EP1992631A1

  公开（公告）日：2008-11-19
• Metal complex compound and organic electroluminescence device using the compound
  申请人：Haga Masa-aki

  公开号：US20070210699A1

  公开（公告）日：2007-09-13

  A metal-complex compound which comprises a tridentate chelate ligand having a specified partial structure. An organic electroluminescence device which comprises one or more organic thin film layers having at least one light emitting layer sandwiched between a pair of electrodes, wherein the organic thin film layer comprises the metal-complex compound, which emits light by applying an electric voltage between the pair of electrodes. The present invention provides an organic EL device which emits blue light of high purity and of short wavelength together with a metal-complex compound realizing the organic EL device.