2,5-bis[4-(bromomethyl)phenyl]-1,3,4-oxadiazole | 58370-39-1

• 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: 2,5-bis[4-(bromomethyl)phenyl]-1,3,4-oxadiazole
• 英文别名: 2,5-Bis(4-bromomethylphenyl)-1,3,4-oxadiazole
• CAS: 58370-39-1
• 化学式: C₁₆H₁₂Br₂N₂O
• 分子量: 408.092
• InChiKey: WOOBPQAPKPZXLS-UHFFFAOYSA-N

物化性质

• 熔点：
  220-222 °C(Solv: tetrahydrofuran (109-99-9))
• 沸点：
  500.4±60.0 °C(Predicted)
• 密度：
  1.644±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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[4-(bromomethyl)phenyl]-1,3,4-oxadiazole 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 5.0h， 生成 2,5-bis[4-(4-N,N-diethylaminostyryl)phenyl]oxadiazole
  参考文献：
  名称：

  Synthesis and Characterization of a Novel Charge Transfer Compound with Large Three-Photon Absorption Cross Section

  摘要：

  利用Wittig-Horner反应合成了一种新型分子内电荷转移化合物，该化合物含有二乙氨基作为电子供体和恶二唑基团作为电子受体。这种长共轭分子具有在 1.06 μm 激光激发下的大三光子吸收截面。

  DOI：

  10.1246/cl.2001.824
• 作为产物：
  描述：

  对甲基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 一水合肼 作用下， 以 四氯化碳 为溶剂， 生成 2,5-bis[4-(bromomethyl)phenyl]-1,3,4-oxadiazole
  参考文献：
  名称：

  高效吸收双光子的多极性对称和不对称N杂环化合物

  摘要：

  设计并合成了一系列具有不同构型的新型多极性对称和不对称N-杂环化合物。通过傅立叶变换红外光谱，氢-1核磁共振和质谱对它们的结构进行了表征。在各种溶剂中系统地研究了它们的光物理性质，包括线性吸收，单光子激发的荧光，双光子吸收和双光子激发的荧光。借助密度泛函理论计算研究了结构与光物理性质之间的关系。

  DOI：

  10.1016/j.jphotochem.2017.05.025

文献信息

• Investigation of the role of 1,3,4-oxadiazole on the spectroscopic, optical, and electrochemical properties of benzimidazolophanes
  作者：Perumal Rajakumar、Sebastian Raja

  DOI：10.1016/j.tetlet.2008.10.142

  日期：2009.1

  The synthesis of 1,3,4-oxadiazole (OXD)-based dicationic cyclophanes has been achieved via an N-alkylation route, and UV–vis spectra proved the absence of charge transfer interactions. Electrochemical studies showed interference of the OXD unit on the characteristic redox properties of dicationic benzimidazolophanes.

  1，3，4-恶二唑（OXD）基二氯环糊精的合成已通过N-烷基化途径完成，UV-vis光谱证明不存在电荷转移相互作用。电化学研究表明，OXD单元干扰了苯并咪唑并苯二酚的特征氧化还原特性。
• Polymer light-emitting diodes based on a bipolar transporting luminescent polymer
  作者：Yanguang Zhang、Yufeng Hu、Hongchao Li、Lixiang Wang、Xiabin Jing、Fosong Wang、Dongge Ma

  DOI：10.1039/b210302h

  日期：2003.3.19

  A soluble electroluminescent polymer containing hole-deficient triphenylamine and electron-deficient oxadiazole units in the main chains has been designed and studied. The design is based on the consideration that the triphenylamine group possesses good hole-transporting property and the oxadiazole unit is known to be of electron-transporting character. Because of the good bipolar transporting performance, the brightness and electroluminescent efficiency are significantly improved and the turn-on voltage is reduced compared with a similar polymer without the electron-deficient oxadiazole units in the main chains. For a device with configuration ITO/PEDOT/polymer/CsF/Al, a maximum brightness of 3600 cd m−2 and a maximum luminescent efficiency of 0.65 cd A−1 (quantum efficiency of 0.3%) were obtained in the polymer with oxadiazole units, about 15 times brighter and 15 times more efficient than the corresponding polymer without oxadiazole units.

  我们设计并研究了一种可溶性电致发光聚合物，其主链中含有空穴缺陷的三苯胺和电子缺陷的噁二唑单元。设计的依据是三苯胺基团具有良好的空穴传输特性，而已知噁二唑单元具有电子传输特性。与主链中没有缺电子的噁二唑单元的类似聚合物相比，由于这种聚合物具有良好的双极传输性能，因此亮度和电致发光效率显著提高，开启电压降低。在配置为 ITO/PEDOT/ 聚合物/CsF/Al 的装置中，含有噁二唑单元的聚合物的最大亮度为 3600 cd m-2，最大发光效率为 0.65 cd A-1（量子效率为 0.3%），亮度和发光效率分别是不含噁二唑单元的相应聚合物的 15 倍和 15 倍。
• Synthesis and optical properties of two novel stilbene derivatives containing 1,3,4-oxadiazole moiety
  作者：Yong-Chuang Zhu、Dao-Hang He、Zhuo-Ru Yang

  DOI：10.1016/j.saa.2008.10.011

  日期：2009.3

  Two novel stilbene derivatives containing 1,3,4-oxadiazole moiety were synthesized and characterized by elemental analyses, 1H NMR, MS. The photophysical processes of the title compounds were investigated by UV–vis absorption and fluorescence emission spectra in different solutions. The fluorescence quantum yield (Φ) of 1a and 1b in THF is 0.65 and 0.69, respectively. The influence of the solution

  合成了两种含有1,3,4-恶二唑部分的新型衍生物，并通过元素分析，1 H NMR，MS进行了表征。通过紫外可见吸收和荧光发射光谱在不同溶液中研究了标题化合物的光物理过程。1a和1b在THF中的荧光量子产率（Φ）分别为0.65和0.69。还讨论了溶液对荧光强度的影响。在紫外光激发下，这两种化合物表现出强烈的蓝色荧光发射。它们可以用作有机电致发光材料中的潜在应用。
• Synthesis and Characterization of Novel Stilbene Derivatives with 1,3,4-Oxadiazole Unit
  作者：Dao-Hang He、Yong-Chuang Zhu、Zhuo-Ru Yang、Ai-Xi Hu

  DOI：10.1002/jccs.200900039

  日期：2009.4

  Four novel stilbene derivatives containing 1,3,4‐oxadiazole unit have been synthesized in four steps with overall yields (27∼35%). The synthetic route involved one‐step installation of 2,5‐di‐p‐tolyl‐1,3,4‐oxadiazol via the direct coupling of p‐toluic acid with hydrazine hydrate promoted by PPA, benzylic bromination, conventional phosphonate formation, and Wittig‐Horner olefination.

  通过四个步骤合成了四个包含1,3,4-恶二唑单元的新型二苯乙烯衍生物，总收率（27％〜35％）。合成途径包括通过对甲苯甲酸与PPA促进的水合肼的直接偶联，苄基溴化，常规膦酸酯的形成和分离，一步法安装2,5-二-对甲苯基-1,3,4-恶二唑。Wittig-Horner烯烃化。
• Synthesis and Optically Acid-Sensory and Electrochemical Properties of Novel Polyoxadiazole Derivatives
  作者：Tzi-Yi Wu、Rong-Bin Sheu、Yun Chen

  DOI：10.1021/ma035576y

  日期：2004.2.1

  A series of PPV-based polyoxadiazoles have been synthesized by Homer and Suzuki coupling polymerization to investigate their structure-property relationship. These copolymers exhibit good thermal stability (decomposition temperature around 352-413 degreesC). Excimer formation in P4-P9 was confirmed by their absorption and PL spectral peak transition in solution at different concentrations and in thin films. Unusual absorption and fluorescence were observed in acid media and have been related to photoinduced charge transfer in alternating donor-acceptor architecture. The photoinduced charge transfer led to a blue shift in iminodibenzyl-containing copolymers (P1-P3) and a red shift in fluorene-containing copolymers (P9), reflecting the fact that iminodibenzyl is a stronger electron-donating unit. The electrochemical properties of the copolymers were evaluated by cyclic voltammetry and their highest occupied molecular orbital and the lowest unoccupied molecular orbit energy levels were estimated. The optical band gaps of the dioxadiazole-containing copolymers show great discrepancy with the electrochemical band gap energy due to the donor-acceptor feature of the dioxadiazole unit.