2-(4-溴苯基)-5-(4-叔丁基苯基)-1,3,4-恶二唑 | 220843-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-溴苯基)-5-(4-叔丁基苯基)-1,3,4-恶二唑
• 英文名称: 2-(4-bromophenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole
• CAS: 220843-12-9
• 化学式: C₁₈H₁₇BrN₂O
• 分子量: 357.25
• InChiKey: QTTKXUVFAFOLAC-UHFFFAOYSA-N

物化性质

• 熔点：
  143.8-144.6 °C
• 沸点：
  444.5±55.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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-(4-溴苯基)-5-(4-叔丁基苯基)-1,3,4-恶二唑 在 正丁基锂 、 硼酸三甲酯 作用下， 以 正己烷 为溶剂， 反应 4.75h， 以42%的产率得到[4-[5-(4-Tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]boronic acid
  参考文献：
  名称：

  Synthesis, structure, photophysical and electrochemical properties of series of new fac-triscyclometallated iridium complexes with carbazole or oxadiazole moieties

  摘要：

  A series of new fac-triscyclometallated iridium complexes Ir(Ln)(3) (n = 1-6) (L-1: 2-{4-[5-phenyl-[1,3,4] oxadiazol-2-yl]-phenyl}-pyridine, L2: 2-{4-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl]-phenyl}pyridine, L3: 9-(4-pyridin-2-yl-phenyl)-9H-carbazole, L4: 1-[4-(5-phenyl-[1,3,4] oxadiazol-2-yl)-phenyl]- isoquinoline, L5: 1-{4-[5-(4-tert-butyl-phenyl)-[1,3,4] oxadiazol-2-yl]-phenyl}-isoquinoline, L6: 9-(4-isoquinolin-1-yl-phenyl)-9H-carbazole) based on Ir(ppy)(3) (ppy = phenyl-pyridine) and Ir(piq)(3) (piq = 1-phenylisoquinoline) were synthesized from Ir(acac)(3) and corresponding ligands by a new and effective way using anthracene as a solvent. Single-crystal X-ray diffraction spectra of three complexes were studied and the iridium centers were found to adopt distorted octahedral coordination geometry. UV-Vis, photoluminescence, cyclic voltammetry were employed for studying the photophysical and electrochemical properties. These complexes exhibit intense phosphorescence in toluene solution at room temperature with high quantum efficiencies (0.07-0.58) and submicrosecond lifetimes (0.57-0.87 mu s). (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.05.010
• 作为产物：
  描述：

  对溴苯甲酰肼 在 吡啶 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-(4-溴苯基)-5-(4-叔丁基苯基)-1,3,4-恶二唑
  参考文献：
  名称：

  用于发光器件的含2,7-二甲氧基咔唑单元的电荷传输嵌段共聚物的合成

  摘要：

  通过NMRP法合成了分别由含2,7-二甲氧基咔唑和恶二唑链段作为空穴和电子传输单元的嵌段共聚物。使用嵌段共聚物，无规共聚物和聚合物共混物作为发光层的Ir（ppy）3作为磷光掺杂剂，制备了OLED器件，以研究形态对性能的影响。从发现EQE中嵌段共聚物体系不堪重负的发现来看，我们认为具有二甲氧基咔唑单元组装在PEDOT：PSS表面的形态对于电荷的有效重组以及足够的电荷注入发光层起着相当重要的作用。

  DOI：

  10.1016/j.polymer.2009.12.024

文献信息

• Propylphosphonic anhydride (T3P®): an efficient reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles
  作者：John Kallikat Augustine、Veeramani Vairaperumal、Sharmila Narasimhan、Padma Alagarsamy、Anbarasi Radhakrishnan

  DOI：10.1016/j.tet.2009.09.114

  日期：2009.11

  Propylphosphonic anhydride (T3P®) has been demonstrated to be an efficient and mild reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles from carboxylic acids.

  丙基膦酸酐（T3P ®）已经以实例阐述是高效和温和的试剂为一锅合成的1,2,4-恶二唑，1,3,4-恶二唑，和选自羧酸1,3,4-噻二唑。
• EMISSIVE COMPOUNDS FOR ORGANIC LIGHT-EMITTING DIODES
  申请人：Froehlich Jesse Dan

  公开号：US20130087772A1

  公开（公告）日：2013-04-11

  Disclosed herein are compounds comprising an optionally substituted (2-phenylpyridinato-N,C2′)(2,4-pentanedionato)Pt(II). Some embodiments provide a light-emitting device, comprising: an anode layer; a cathode layer; and a light-emitting layer positioned between, and electrically connected to, the anode layer and the cathode layer, wherein the light-emitting layer comprises a compound disclosed herein.

  本文披露了包含可选择取代的(2-苯基吡啶基-N,C2′)(2,4-戊二酮基)Pt(II)的化合物。一些实施例提供了一种发光装置，包括：阳极层；阴极层；以及位于阳极层和阴极层之间并与之电连接的发光层，其中该发光层包括本文披露的化合物。
• Molecular Wires Comprising π-Extended Ethynyl- and Butadiynyl-2,5-Diphenyl-1,3,4-Oxadiazole Derivatives:  Synthesis, Redox, Structural, and Optoelectronic Properties
  作者：Changsheng Wang、Lars-Olof Pålsson、Andrei S. Batsanov、Martin R. Bryce

  DOI：10.1021/ja0577600

  日期：2006.3.1

  5-Diphenyl-1,3,4-oxadiazole (OXD) derivatives with terminal ethynyl- (4a,b) and butadiynyl- (8a,b) substituents have been synthesized in high yields. 2-Methyl-3,5-hexadiyn-2-ol has not been exploited previously in the synthesis of terminal butadiynes. Crystals of 8a and 8b are remarkably stable to long-term storage under ambient conditions. The X-ray crystal structure of 8a reveals that the butadiyne

  具有末端乙炔基-(4a,b) 和丁二炔基-(8a,b) 取代基的 2,5-二苯基-1,3,4-恶二唑 (OXD) 衍生物已以高产率合成。2-Methyl-3,5-hexadiyn-2-ol 以前没有被用于合成末端丁二炔。8a 和 8b 的晶体在环境条件下对长期储存非常稳定。8a 的 X 射线晶体结构显示丁二炔部分被芳香部分空间隔离，这解释了高稳定性。两个衍生的pi-共轭分子，Donor-(C[triple bond]C)(n)-OXD (n = 1, 2) 和OXD-(C[triple bond]C)(n)-Donor-(C) [三键]C)(n)-OXD (n = 1) [供体 = 四硫富瓦烯 (TTF)、联噻吩、9-(4,5-二甲基-1,3-二硫醇-2-亚基)芴和三苯胺] , 已使用 Sonogashira 反应合成，并通过 X 射线晶体学、循环伏安法和光学吸收/发射光谱进行表征。OXD
• New electroluminescent bipolar compounds for balanced charge-transport and tuneable colour in organic light emitting diodes: triphenylamine–oxadiazole–fluorene triad molecules
  作者：Kiran T. Kamtekar、Changsheng Wang、Sylvia Bettington、Andrei S. Batsanov、Igor F. Perepichka、Martin R. Bryce、Jin H. Ahn、Mohammad Rabinal、Michael C. Petty

  DOI：10.1039/b604543j

  日期：——

  This work describes bipolar 2,5-diaryl-1,3,4-oxadiazole–fluorene hybrids which incorporate triphenylamine or carbazole units within the π-electron system, viz. compounds 7, 8, 14 and 16. A related bipolar bis(oxadiazolyl)pyridine system 20 is reported. The syntheses of these five new materials are discussed, along with their optoelectronic absorption and emission properties, and their solution electrochemical redox properties. Anodic electropolymerisation of 20 was observed. Calculations using DFT (density functional theory) establish that they all possess a significantly higher HOMO energy level (by 0.60–1.02 eV) than 1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazol-5-yl]benzene (OXD-7) due to the presence of electron-rich amine moieties and increased conjugation lengths, thereby leading to more balanced charge-transport characteristics. Devices were fabricated by spin-coating techniques using the bipolar compounds as the emitters in the simple device architecture ITO:PEDOT-PSS:X:Ca/Al (X = 7, 8, 14, 16 or 20). The turn-on voltages were 2.9, 5.5, 3.6, 4.5 and 3.4 V for the devices incorporating 7, 8, 14, 16 and 20, respectively. The highest external quantum efficiency (EQE) was observed for compound 7: viz. EQE 0.36%; current efficiency 1.00 cd A−1; power efficiency 0.56 lm W−1 at 5.7 V. The EQE of the device fabricated from 8 was considerably lower than for devices using other materials due to low light emission. The EL emission peaked at λmax 430, 487, 487 and 521 nm for 8, 14 and 16, and 7, respectively. For the 20 device λmax = 521 nm and 564 nm. Thus the HOMO–LUMO gap has been modified, allowing the colour of the emitted light to vary from light blue through to green by the systematic chemical modification of the molecular subunits. The high chemical and thermal durability of these materials combined with the simplicity of the device structure and low turn-on voltages offers considerable potential for OLED applications.

  本工作描述了包含三苯胺或咔唑单元的双极性2,5-二芳基-1,3,4-噁二唑-荧光烯杂化物，即化合物7、8、14和16。还报道了一种相关的双极性双(噁二唑基)吡啶系统20。讨论了这五种新材料的合成，以及它们的光电吸收和发射特性及其溶液电化学氧还原特性。观察到20的阳极电化学聚合。使用密度泛函理论（DFT）计算表明，它们的HOMO能级明显高于1,3-双[2-(4-叔丁基苯基)-1,3,4-噁二唑-5-基]苯（OXD-7），提高了0.60–1.02 eV，这得益于富电子的胺基团和增加的共轭链长，从而导致更均衡的电荷传输特性。通过旋涂技术制造了器件，将这些双极性化合物作为发射体用于简单的器件结构ITO:PEDOT-PSS:X:Ca/Al（X = 7、8、14、16或20）。融入7、8、14、16和20的器件的开启电压分别为2.9、5.5、3.6、4.5和3.4 V。化合物7的外量子效率（EQE）最高：即EQE 0.36%；电流效率1.00 cd A⁻¹；在5.7 V时，功率效率为0.56 lm W⁻¹。由8制成的器件的EQE明显低于使用其他材料的器件，原因是发光较弱。EL发射在8、14、16和7时分别达到峰值λmax 430、487、487和521 nm。对于20器件，λmax = 521 nm和564 nm。因此，HOMO–LUMO间隙得到了调节，使得发出光的颜色可以通过分子亚单位的系统化化学修饰从浅蓝色变化到绿色。这些材料的高化学和热稳定性，加上器件结构的简易性和低开启电压，为OLED应用提供了可观的潜力。
• Synthesis and characterization of donor-acceptor poly(3-hexylthiophene) copolymers presenting 1,3,4-oxadiazole units and their application to photovoltaic cells
  作者：Hsu-Shen Wang、Ming-Shin Su、Kung-Hwa Wei

  DOI：10.1002/pola.24117

  日期：——

  metathesis polymerization to prepare poly(3‐hexylthiophene)‐based copolymers containing electron‐withdrawing 4‐tert‐butylphenyl‐1,3,4‐oxadiazole‐phenyl moieties as side chains. We characterized these copolymers using 1H and 13C nuclear magnetic resonance spectroscopy, thermogravimetric analysis, and gel permeation chromatography. The band gap energy of copolymer was determined from the onset of the

  我们已经使用格利雅（Grignard）复分解聚合反应制备了基于聚（3-己基噻吩）的共聚物，该共聚物含有吸电子的4-叔丁基苯基-1,3,4-恶二唑苯基部分作为侧链。我们使用1 H和13表征了这些共聚物C核磁共振波谱，热重分析和凝胶渗透色谱。共聚物的带隙能由光吸收的开始确定。在共聚物的光致发光光谱中观察到了淬灭作用，该共聚物在侧链上结合了电子侧链缺失的1,3,4-恶二唑部分。在存在最适量的1,3,4-恶二唑部分的情况下，器件的光电流得以增强，从而提高了功率转换效率。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem 48：3331-3339，2010年