2-(4-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole | 23133-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-phenyl-5-(p-hydroxyphenyl)-1,3,4-oxadiazole；2-(4-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazol；4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-phenol；p-(5-phenyl-1,3,4-oxadiazole-2-yl) phenol；4-(5-phenyl-[1,3,4]oxadiazol-2-yl)phenol；p-(5-phenyl-1,3,4-oxadiazole-2-yl)phenol；4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenol
• CAS: 23133-34-8
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: NEIGDUNVPSHESZ-UHFFFAOYSA-N

物化性质

• 熔点：
  254.5-255 °C
• 沸点：
  439.3±47.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole 在 过氧化苯甲酰 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 2-(10'-(p-(5"-phenyl-1",3",4"-oxadiazol-2-yl)phenoxy)decanoxy)-1,4-bis(bromomethyl)benzene
  参考文献：
  名称：

  Soluble Electroluminescent Poly(phenylene vinylene)s with Balanced Electron- and Hole Injections

  摘要：

  We report a new route for the design of efficient soluble electroluminescent PPV-based copolymers bearing electron-deficient oxadiazole (OXD) moieties on side chains. The introduction of OXD through a long alkylene spacer with PPV backbone provides a molecular dispersion of OXD in the film; both the side chain OXD and the main chain PPV do retain their own electron-transport and emissive properties, respectively. The use of phenylene vinylene derivatives with asymmetric and branched substituents and a long spacer provides solubility for ease of device fabrication as well as amorphous structure to allow a well-mixing of OXD groups with the main chains. By properly adjusting the OXD content through copolymerization, we can tailor the chemical structure of electroluminescent material to give a balance of hole- and electron injections for various metal cathodes, such that the quantum efficiency is significantly improved and the turn-on voltage is reduced for the devices with aluminum and calcium. For the device with calcium fabricated in open air, a maximum brightness of 15000 cd/m(2) at 15 V/100 nm and a maximum luminance efficiency of 2.27 cd/A can be obtained, respectively, about 30 times brighter and 9.4 times more efficient than those with the corresponding homopolymer, poly[2-methoxy-5-(2'-ethylhexyloxy)-p-phenylenevinylene] (MEH-PPV). The use of physical blends to simulate the copolymers provides no significant improvement, since phase-separation structures appear, causing an inefficient utilization of OXD and sometimes voltage-dependent emission spectra. The present route permits a fabrication of single layer PLED with high brightness, high efficiency, and low turn-on voltage.

  DOI：

  10.1021/ja003135d
• 作为产物：
  描述：

  对甲氧基苯甲酰肼 在 吡啶 、 三氯化铝 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 2-(4-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Jacobsen, Noel W.; Philippides, Athena E., Australian Journal of Chemistry, 1986, vol. 39, # 11, p. 1911 - 1914

  摘要：

  DOI：

文献信息

• Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents
  作者：Sushma Singh、Laxmi Kant Sharma、Apoorv Saraswat、Ibadur R. Siddiqui、Harbans K. Kehri、Rana K. Pal Singh

  DOI：10.1039/c3ra21904f

  日期：——

  The electrochemical oxidation of aldehyde-N-aroylhydrazone has been studied in the presence of NaClO4 as supporting electrolyte in MeOH solution using cyclic voltammetry and controlled potential electrolysis. The results indicate that intramolecular cyclization of aldehyde-N-aroylhydrazone has been successfully performed at a platinum electrode in an undivided cell with good yields of the corresponding 1,3,4-oxadiazoles at ambient conditions. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The antifungal activity of the synthesized compounds was evaluated on Fusarium oxysporum, Alternaria solani, Candida albicans and Aspergillus niger. The results revealed that all the synthesized compounds have significant antifungal activity against the tested fungi. Among the synthesized derivatives 7b, 7d, 7g, 7h, 7i, 7j and 7r were found to be the most effective antifungal compounds.

  在甲醇溶液中，以NaClO4为支持电解质，通过循环伏安法和控制电位电解法研究了醛-N-芳酰腙的电化学氧化反应。结果表明，在室温条件下，在不分隔的铂电极反应池中，醛-N-芳酰腙成功进行了分子内环化反应，得到了较高产率的相应1,3,4-噁二唑类化合物。通过光谱方法对反应产物进行了表征，并从伏安法研究中推导出反应机理。对合成化合物进行了对 Fusarium oxysporum、Alternaria solani、Candida albicans 和 Aspergillus niger 的抗真菌活性评估。结果显示，所有合成化合物对测试的真菌均显示出显著的抗真菌活性。其中，合成衍生物 7b、7d、7g、7h、7i、7j 和 7r 被发现是最高效的抗真菌化合物。
• 2,4,6-Tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine as a New Recyclable Hypervalent Iodine(III) Reagent for Chlorination and Oxidation Reactions
  作者：Nandkishor Karade、Prerana Thorat、Bhagyashree Bhong

  DOI：10.1055/s-0033-1339495

  日期：——

  reagent 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine can be applied also for the oxidative synthesis of 1,3,4-oxadiazoles and 1,2,4-thiadiazoles under mild conditions in excellent yields. The recyclability of the 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine was possible owing to the facile recovery and reuse of the coproduced 2,4,6-tris(4-iodophenoxy)-1,3,5-triazine from the reaction mixture

  2,4,6-三[(4-二氯碘)苯氧基)]-1,3,5-三嗪作为（二氯碘）苯的一种新型可回收非聚合类似物的合成分两步完成，使用2,4， 6-三氯-1,3,5-三嗪和4-碘苯酚。2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine 在各种活化芳烃、烯烃和 1,3-二酮的氯化反应中的应用得到了证明。试剂2,4,6-三[(4-二氯碘)苯氧基)]-1,3,5-三嗪也可用于1,3,4-恶二唑和1,2,4-噻二唑的氧化合成在温和的条件下以优异的产量。由于联产的 2,4,6-三(4-二氯碘)苯氧基)]-1,3,5-三嗪易于回收和再利用，2,4,6-三[(4-二氯碘)苯氧基)]-1,3,5-三嗪的可回收性是可能的。碘苯氧基)-1,3,5-三嗪从反应混合物中分离出来，因为它实际上不溶于甲醇。
• The spectrophotometric study of a fluorescence-enhanced inclusion complex threaded with β-cyclodextrin: Synthesis and characterization
  作者：Yi-Hong Chiu、Jui-Hsiang Liu

  DOI：10.1002/pola.24121

  日期：——

  group and threaded through β‐cyclodextrin was synthesized to investigate the host‐guest interactions in the inclusion complex. 1H NMR studies revealed that one or two cyclodextrin molecules were threaded onto the synthesized achiral monomer, leading to the formation of a fibrous construction of self‐assembled inclusion complexes. The formation of a self‐assembled inclusion complex was identified using SEM

  合成了一种新的非手性单体，该单体被苯基[1,3,4]恶二唑基封端，并通过β-环糊精连接，以研究包合物中宿主与客体之间的相互作用。1个1 H NMR研究表明，将一个或两个环糊精分子穿线到合成的非手性单体上，导致形成自组装包合物的纤维结构。使用SEM和TEM鉴定了自组装包合物的形成。使用偏振光学显微镜证实了自组装超分子的高度有序排列。我们证明了在吡啶/乙醇（1 mL / 10 mL）中制备纳米结构的自组装包合物的简单方法，以及通过用苯基[1]封端的单体增强光致荧光的方法， 3,4]恶二唑基部分带有β-环糊精。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem 48：3368–3374，2010年
• Synthesis, optophysical and electrochemical properties of bipolar-transporting europium(III) complexes with carbazole and oxadiazole units
  作者：Liang Li、Yu Liu、Haipeng Guo、Yafei Wang、Yunbo Cao、Aihui Liang、Hua Tan、Hongrui Qi、Meixiang Zhu、Weiguo Zhu

  DOI：10.1016/j.tet.2010.07.003

  日期：2010.9

  series of bipolar-transporting europium(III) complexes containing carbazole and oxadiazole units were synthesized and characterized. Two intense UV absorption bands at around 286 nm and 352 nm, and sharply red emissions peaked at 614 nm were observed for these europium complexes in dichloromethane. Importantly, the bipolar-transporting europium(III) complexes exhibited higher thermal stability, more intense

  合成并表征了一系列含有咔唑和恶二唑单元的双极传输euro（III）配合物。对于这些euro络合物在二氯甲烷中，观察到两个强烈的紫外吸收带，分别在286 nm和352 nm处，并且在614 nm处出现红色峰值。重要的是，与报道的三（二苯甲酰甲烷）（1,10-菲咯啉）euro（III）的红色生色团相比，双极传输-（III）配合物表现出更高的热稳定性，更强的紫外线在286 nm处的吸收以及两倍的光致发光量子产率。 ）。
• 용액공정이 가능한 신규한 이리듐(ＩＩＩ) 착화합물 및 이를 포함하는 유기전계발광소자
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR101567784B1

  公开（公告）日：2015-11-11

  본 발명은 용액공정이 가능한 신규한 이리듐(III) 착화합물 및 이를 포함하는 유기전계발광소자에 관한 것으로, 보다 상세하게는, 주리간드로서 퀴놀린 및 티오펜 유도체가 도입되어 있고 보조리간드로 피콜리닉산의 질소 원자에 대하여 파라 위치에 할로겐 유도체 또는 전자수송 특성을 나타내는 옥사디아졸 유도체가 치환된 피콜리닉산 유도체가 도입된 신규한 이리듐(III) 착화합물 및 상기 이리듐(III) 착화합물을 포함하는 유기전계발광소자에 관한 것이다. 본 발명에 따른 이리듐(III) 착화합물은 전기적 안정성이 우수하고, 높은 발광 특성과 휘도를 가지며 색순도 구현이 가능한 적색 인광 발광 화합물로, 유기용매에 대한 향상된 가용성과 내열성으로 전극과의 계면 특성이 우수해 유기전계발광소자의 발색재료로서 유용하다.

  本发明涉及一种新的铱(III)配合物，可用于溶液工艺，以及包含该铱(III)配合物的有机电致发光器件，更详细地说，涉及一种含有喹啉和硫代吩衍生物的主配体，以及在辅助配体中，对吡啶甲酸的氮原子进行取代的新型铱(III)配合物，其中在对位取代了卤素衍生物或表现出电子传输特性的氧代噁唑衍生物的吡啶甲酸衍生物。本发明涉及含有上述铱(III)配合物的有机电致发光器件。根据本发明，铱(III)配合物具有优异的电学稳定性，具有高发光特性和亮度，并且可以实现色度的红色光发射化合物，具有改善有机溶剂溶解性和耐热性，优越的与电极的界面特性，作为有机电致发光器件的发光材料非常有用。