2-(4-fluorophenyl)-5-(2,4,6-tri-tert-butylphenyl)-1,2,4-oxadiazole | 1283116-63-1

• 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: 2-(4-fluorophenyl)-5-(2,4,6-tri-tert-butylphenyl)-1,2,4-oxadiazole
• 英文别名: 2-(4-Fluorophenyl)-5-(2,4,6-tritert-butylphenyl)-1,3,4-oxadiazole；2-(4-fluorophenyl)-5-(2,4,6-tritert-butylphenyl)-1,3,4-oxadiazole
• CAS: 1283116-63-1
• 化学式: C₂₆H₃₃FN₂O
• 分子量: 408.559
• InChiKey: VZUFUSRWXZJPEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-5-(2,4,6-tri-tert-butylphenyl)-1,2,4-oxadiazole 、 三氯化铱 以 乙二醇乙醚 、 水 为溶剂， 以14%的产率得到
  参考文献：
  名称：

  2,5-二芳基-1,3,4-恶二唑衍生物的异常双核和单核环金属铱配合物

  摘要：

  的新的2,5-二苯基-1,3,4-恶二唑（OXD）衍生物家族8 - 11轴承邻报道烷基取代基在苯环上的一个。在标准环金属化条件下，这些OXD与IrCl 3的反应未得到通常的μ-二氯桥联二铱OXD络合物。取而代之的是，新颖的二铱络合物12 - 14和复合物中的monoiridium 15被分离并通过X射线晶体学。有人提出，异常结构是由于邻位而产生的。-烷基取代基会导致部分OXD系统发生实质性扭曲，由于空间原因，这种扭曲会改变金属-配体配位反应的正常过程。的后续反应13和15，得到单核配合物16 - 18与ACAC和吡啶甲酸anciliary配体。报告了16和18的晶体结构。在室温下在绿色（16）和蓝绿色区域（17和18）中观察到光致发光。配合物16 - 18是在77K的低温磷光，具有三重态的4.2-5.7微秒寿命

  DOI：

  10.1021/ic102153x
• 作为产物：
  描述：

  对氟苯腈 在 吡啶 、 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-fluorophenyl)-5-(2,4,6-tri-tert-butylphenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Bipolar Molecules with High Triplet Energies: Synthesis, Photophysical, and Structural Properties

  摘要：

  This article sheds new light on the interplay of electronic and conformational effects in luminescent bipolar molecules. A series of carbazole/1,3,4-oxadiazole hybrid molecules is described in which the optoelectronic properties are systematically varied by substituent effects which tune the intramolecular torsion angles. The synthesis, photophysical properties, cyclic voltammetric data, X-ray crystal structures, and DFT calculations are presented. Excited state intramolecular charge transfer (ICT) is observed from the donor carbazole/2,7-dimethoxycarbazole to the acceptor phenyl/diphenyloxadiazole moieties. Introducing more bulky substituents onto the diphenyloxadiazole fragment systematically increases the singlet and triplet energy levels (E-S and E-T) and blue shifts the absorption and emission bands. The triplet excited state is located mostly on the oxadiazole unit. The introduction of 2,7-dimethoxy substituents onto the carbazole moiety lowers the value of E-S, although E-T is unaffected, which means that the singlet triplet gap is reduced (for 7b E-S - E-T = 0.61 eV). A strategy has been established for achieving unusually high triplet levels for bipolar molecules (E-T = 2.64-2.78 eV at 14 K) while at the same time limiting the increase in the singlet energy.

  DOI：

  10.1021/jo201488v

文献信息

• Bipolar Molecules with High Triplet Energies: Synthesis, Photophysical, and Structural Properties
  作者：Yonghao Zheng、Andrei S. Batsanov、Vygintas Jankus、Fernando B. Dias、Martin R. Bryce、Andrew P. Monkman

  DOI：10.1021/jo201488v

  日期：2011.10.21

  This article sheds new light on the interplay of electronic and conformational effects in luminescent bipolar molecules. A series of carbazole/1,3,4-oxadiazole hybrid molecules is described in which the optoelectronic properties are systematically varied by substituent effects which tune the intramolecular torsion angles. The synthesis, photophysical properties, cyclic voltammetric data, X-ray crystal structures, and DFT calculations are presented. Excited state intramolecular charge transfer (ICT) is observed from the donor carbazole/2,7-dimethoxycarbazole to the acceptor phenyl/diphenyloxadiazole moieties. Introducing more bulky substituents onto the diphenyloxadiazole fragment systematically increases the singlet and triplet energy levels (E-S and E-T) and blue shifts the absorption and emission bands. The triplet excited state is located mostly on the oxadiazole unit. The introduction of 2,7-dimethoxy substituents onto the carbazole moiety lowers the value of E-S, although E-T is unaffected, which means that the singlet triplet gap is reduced (for 7b E-S - E-T = 0.61 eV). A strategy has been established for achieving unusually high triplet levels for bipolar molecules (E-T = 2.64-2.78 eV at 14 K) while at the same time limiting the increase in the singlet energy.
• Unusual Dinuclear and Mononuclear Cyclometalated Iridium Complexes of 2,5-Diaryl-1,3,4-oxadiazole Derivatives
  作者：Yonghao Zheng、Andrei S. Batsanov、Martin R. Bryce

  DOI：10.1021/ic102153x

  日期：2011.4.18

  phenyl rings is reported. The reactions of these OXDs with IrCl3 under standard cyclometalating conditions did not give the usual μ-dichloro bridged diiridium OXD complexes. Instead, the novel diiridium complexes 12−14 and the monoiridium complex 15 were isolated and characterized by X-ray crystallography. It is proposed that the unusual structures arise because of the ortho-alkyl substituents leading to

  的新的2,5-二苯基-1,3,4-恶二唑（OXD）衍生物家族8 - 11轴承邻报道烷基取代基在苯环上的一个。在标准环金属化条件下，这些OXD与IrCl 3的反应未得到通常的μ-二氯桥联二铱OXD络合物。取而代之的是，新颖的二铱络合物12 - 14和复合物中的monoiridium 15被分离并通过X射线晶体学。有人提出，异常结构是由于邻位而产生的。-烷基取代基会导致部分OXD系统发生实质性扭曲，由于空间原因，这种扭曲会改变金属-配体配位反应的正常过程。的后续反应13和15，得到单核配合物16 - 18与ACAC和吡啶甲酸anciliary配体。报告了16和18的晶体结构。在室温下在绿色（16）和蓝绿色区域（17和18）中观察到光致发光。配合物16 - 18是在77K的低温磷光，具有三重态的4.2-5.7微秒寿命