5-(4-fluoro-3-methylphenyl)-1H-tetrazole | 1020969-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-fluoro-3-methylphenyl)-1H-tetrazole
• 英文别名: 5-(4-fluoro-3-methylphenyl)-1H-1,2,3,4-tetrazole；5-(4-fluoro-3-methylphenyl)-2H-tetrazole
• CAS: 1020969-35-0
• 化学式: C₈H₇FN₄
• mdl: MFCD11155438
• 分子量: 178.169
• InChiKey: BAEILIBQGFTITB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-fluoro-3-methylphenyl)-1H-tetrazole 在 吡啶 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 2-[4-(2,7-dimethoxy-9H-carbazol-9-yl)phenyl]-5-(2,4,6-trimethylphenyl)-1,3,4-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
• 作为产物：
  描述：

  4-氟-3-甲基苯腈 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到5-(4-fluoro-3-methylphenyl)-1H-tetrazole
  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