2,5-bis(2-naphthyl)-1,3,4-oxadiazole | 802-51-7

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,5-bis(2-naphthyl)-1,3,4-oxadiazole
• 英文别名: 2,5-di(naphthalen-2-yl)-1,3,4-oxadiazole；2,5-Bis-naphthyl-(2)-1,3,4-oxdiazol；di-(β-naphthyl)-oxadiazole；Bis<2,5-naphthyl-(2)>-1,3,4-oxdiazol；2,5-Bis-<2>naphthyl-1,3,4-oxadiazol；2,5-Di-<2>-naphthyl-<1,3,4>oxadiazol；2,5-di(2-naphthyl)-1,3,4-oxadiazole；2,5-Di(2-naphthyl)-1,3,4-oxadiazol；di-[2]naphthyl-[1,3,4]oxadiazole；Di-[2]naphthyl-[1,3,4]oxadiazol；2,5-dinaphthalen-2-yl-1,3,4-oxadiazole
• CAS: 802-51-7
• 化学式: C₂₂H₁₄N₂O
• 分子量: 322.366
• InChiKey: NQDGITXYARLRTF-UHFFFAOYSA-N

物化性质

• 熔点：
  187-188 °C(Solv: toluene (108-88-3))
• 沸点：
  556.4±33.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis(2-naphthyl)-1,3,4-oxadiazole 、 对甲苯磺酸甲酯 生成 3-methyl-2,5-di-naphthalen-2-yl-[1,3,4]oxadiazolium; toluene-4-sulfonate
  参考文献：
  名称：

  Recyclization reactions of heterocyles. XVII. Hydrazination of 1, 3, 4-oxadiazolium salts

  摘要：

  DOI：

  10.1007/bf00470105
• 作为产物：
  描述：

  2-萘甲酸甲酯 在 PPA 、 一水合肼 作用下， 以 甲醇 为溶剂， 生成 2,5-bis(2-naphthyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Properties of Acene Dimers Linked by a 1,3,4-Oxadiazole Spacer

  摘要：

  Acene dimers linked by a 1,3,4-oxadiazole spacer were synthesized and their physical, optical, and electrochemical properties were investigated. The melting points and electron affinities of the dimers increased in the following order: benzene, naphthalene, and anthracene. The longest absorption maximum was red-shifted with an increase in the number of benzene rings. The Tc-conjugation between the two acene moieties through the oxadiazole spacer was not strong. Although no OFET properties were observed in a bottom contact device using the anthracene dimer as an active layer, the molecules were perpendicularly arranged on the substrate to form n-stacking films as observed in the X-Ray diffraction analysis.

  DOI：

  10.3987/com-06-s(k)4

文献信息

• Photoredox/Cobalt-Catalyzed Cascade Oxidative Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles under Oxidant-Free Conditions
  作者：Jun-Li Li、Hao-Yuan Li、Shan-Shan Zhang、Shigang Shen、Xiu-Long Yang、Xiaoying Niu

  DOI：10.1021/acs.joc.3c01078

  日期：2023.11.3

  An efficient oxidant-free, photoredox-mediated cascade cyclization strategy for the synthesis of 1,3,4-oxadiazoles by using an organo acridinium photocatalyst and a cobaloxime catalyst has been developed. Various acylhydrazones have been transformed into the corresponding 1,3,4-oxadiazole products in up to 96% yield, and H2 is the only byproduct. Mechanistic experiments and density functional theory

  通过使用有机吖啶光催化剂和钴肟催化剂，开发了一种有效的无氧化剂、光氧化还原介导的级联环化策略，用于合成 1,3,4-恶二唑。各种酰腙已转化为相应的1,3,4-恶二唑产品，收率高达96%，H 2是唯一的副产物。机理实验和密度泛函理论 (DFT) 计算研究表明，光激发 Mes–Acr + *氧化以及去质子化产生的 π 自由基是以碳为中心的自由基，而不是以氧为中心的自由基，这是造成这种转变的原因。该方法的实用性突出是直接从市售醛和酰肼开始的一锅克级合成。
• An electroluminescent element
  申请人：ASAHI KASEI KOGYO KABUSHIKI KAISHA

  公开号：EP0532798A1

  公开（公告）日：1993-03-24

  Disclosed is an electroluminescent element comprising an anode, a cathode and, disposed therebetween, an organic luminescent layer comprising a mixture of a fluorescent luminescent agent, at least one hole moving and donating agent capable of moving holes and donating the same to the luminescent agent and at least one electron moving and donating agent capable of moving electrons and donating the same to the luminescent agent. In the element, the components of the luminescent layer have specific oxidation potential and reduction potential relationships. The element emits light in response to electrical signals. The element exhibits high luminescence efficiency and brightness even at low voltages, and it can efficiently be produced at low cost.

  本发明公开了一种电致发光元件，该元件包括阳极、阴极和置于其间的有机发光层，有机发光层包括荧光发光剂、至少一种能够移动空穴并将空穴捐献给发光剂的空穴移动和捐献剂以及至少一种能够移动电子并将电子捐献给发光剂的电子移动和捐献剂的混合物。在元件中，发光层的各组分具有特定的氧化电位和还原电位关系。该元件在电信号的作用下发光。这种元件即使在低电压下也能表现出很高的发光效率和亮度，而且能以低成本高效生产。
• Mueller; Herrdegen, Journal fur praktische Chemie (Leipzig 1954), 1921, vol. <2> 102, p. 132
  作者：Mueller、Herrdegen

  DOI：——

  日期：——
• Synthesis and properties of iridium complexes based 1,3,4-oxadiazoles derivatives
  作者：Zhaowu Xu、Yang Li、Xuemei Ma、Xindong Gao、He Tian

  DOI：10.1016/j.tet.2007.11.099

  日期：2008.2

  A series of iridium complexes with 2,5-diaryl-[1,3,4]-oxadiazole ligands were synthesized and their electrochemical, photophysical, and electroluminescent (EL) properties studied. It was found that electron-withdrawing or donating substituents on the phenyl ring affected the emission maxima. Complex 3, iridium(IR) bis(2,5-bis-(2-hydroxyphenyl)-[1,3,4]oxadiazolato-C-2, N-3) (acetyl acetonate), was characterized by single-crystal X-ray structural determination. Three organic light emitting diodes devices were fabricated, which showed stable green-yellow luminescence. (C) 2007 Elsevier Ltd. All rights reserved.
• Tashtoush, Hasan; Al-Talib, Mahmoud; Odeh, Nedal, Liebigs Annalen der Chemie, 1992, # 3, p. 291 - 292
  作者：Tashtoush, Hasan、Al-Talib, Mahmoud、Odeh, Nedal

  DOI：——

  日期：——