2-Naphthalen-2-yl-5-[6-(5-naphthalen-2-yl-1,3,4-oxadiazol-2-yl)naphthalen-2-yl]-1,3,4-oxadiazole | 167634-34-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Naphthalen-2-yl-5-[6-(5-naphthalen-2-yl-1,3,4-oxadiazol-2-yl)naphthalen-2-yl]-1,3,4-oxadiazole
• 英文别名: 2-naphthalen-2-yl-5-[6-(5-naphthalen-2-yl-1,3,4-oxadiazol-2-yl)naphthalen-2-yl]-1,3,4-oxadiazole
• CAS: 167634-34-6
• 化学式: C₃₄H₂₀N₄O₂
• 分子量: 516.558
• InChiKey: PGEWXDIBAYHIML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 三氯氧磷 作用下， 以44%的产率得到2-Naphthalen-2-yl-5-[6-(5-naphthalen-2-yl-1,3,4-oxadiazol-2-yl)naphthalen-2-yl]-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and properties of naphthalene trimers linked by 1,3,4-oxadiazole spacers

  摘要：

  Two types of naphthalene trimers linked by 1,3,4-oxadiazole spacers were synthesized and investigated for their physical and electronic properties. 2,6- and 2,7-isomers on central naphthalene moieties were obtained in the forms of pale yellow solids and colorless crystals, respectively. The melting point of the 2,6-isomer was higher than that of the 2,7-isomer. An X-ray crystallographic analysis revealed a pi-stacked column with a short intermolecular distance in the crystals of the 2,6-isomer. The absorption maximum of the 2,6-isomer was red-shifted as compared to that of the 2,7-isomer, indicating a pi-conjugation between di-2-naphthyloxadiazole moieties in the 2,6-isomer. The quantum yields of the 2,6- and 2,7-isomers were measured to be 0.97 and 0.74, relative to that of 2.5-di-2-naphthyl-1.3,4-oxadiazole (0.85). Molecular orbital (MC) calculations demonstrated that the 2,6-isomer had a higher electron affinity than the 2,7-isomer. Thus, the crosslinking of building blocks is important for the design of functional materials. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.122

文献信息

• Synthesis and properties of naphthalene trimers linked by 1,3,4-oxadiazole spacers
  作者：Katsuhiko Ono、Hiroki Ito、Akihiro Nakashima、Mariko Uemoto、Masaaki Tomura、Katsuhiro Saito

  DOI：10.1016/j.tetlet.2008.07.122

  日期：2008.9

  Two types of naphthalene trimers linked by 1,3,4-oxadiazole spacers were synthesized and investigated for their physical and electronic properties. 2,6- and 2,7-isomers on central naphthalene moieties were obtained in the forms of pale yellow solids and colorless crystals, respectively. The melting point of the 2,6-isomer was higher than that of the 2,7-isomer. An X-ray crystallographic analysis revealed a pi-stacked column with a short intermolecular distance in the crystals of the 2,6-isomer. The absorption maximum of the 2,6-isomer was red-shifted as compared to that of the 2,7-isomer, indicating a pi-conjugation between di-2-naphthyloxadiazole moieties in the 2,6-isomer. The quantum yields of the 2,6- and 2,7-isomers were measured to be 0.97 and 0.74, relative to that of 2.5-di-2-naphthyl-1.3,4-oxadiazole (0.85). Molecular orbital (MC) calculations demonstrated that the 2,6-isomer had a higher electron affinity than the 2,7-isomer. Thus, the crosslinking of building blocks is important for the design of functional materials. (C) 2008 Elsevier Ltd. All rights reserved.