2-(pyridin-2-yl)-5-(p-tolyl)-1,3,4-oxadiazole | 1171635-04-3

• 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-(pyridin-2-yl)-5-(p-tolyl)-1,3,4-oxadiazole
• 英文别名: 2-(5-p-tolyl-1,3,4-oxadiazol-2-yl)pyridine；2-(4-Methylphenyl)-5-pyridin-2-yl-1,3,4-oxadiazole
• CAS: 1171635-04-3
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: BSBRCQTYWXCLCW-UHFFFAOYSA-N

物化性质

• 沸点：
  413.0±47.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  五羰基溴铼(I) 、 2-(pyridin-2-yl)-5-(p-tolyl)-1,3,4-oxadiazole 以 甲苯 为溶剂， 反应 12.0h， 生成 C₁₇H₁₁BrN₃O₄Re
  参考文献：
  名称：

  Oxygen optical sensing by doping a rhenium complex into a silica matrix: Design, characterization and performance

  摘要：

  The present paper synthesized a diamine ligand having an oxadiazole group and its Re(I) complex to investigate their potential for oxygen sensing. Conjugation chain in this ligand was increased so that collision probability between excited state electrons and O-2 molecules could be increased, favoring oxygen sensing. This Re(I) complex was confirmed and analyzed by single crystal structure, density functional theory calculation and photophysical measurement. It showed an emission peaking at 552 nm with two long-lived emissive components. Using a silica matrix of MCM-41, oxygen sensing performance of the resulting composite samples was analyzed and compared in detail. An optimal sample gave the highest sensitivity of 5.65 with short response time of 8 s. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.09.024
• 作为产物：
  描述：

  对甲基苯甲酸 在 氯化亚砜 作用下， 以 吡啶 为溶剂， 生成 2-(pyridin-2-yl)-5-(p-tolyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, characterization and striking photoluminescence variation of a series of copper(I) complexes containing oxadiazole ligand

  摘要：

  A series of novel photoluminescent copper(I) complexes with the formula [Cu(P-P)(L)]BF4, where P-P = triphenylphosphine (PPh3) (1, 2), bis[2-(diphenylphosphino)phenyl]-ether (POP)(3, 4), L = 2-phenyl-5-(pyridin-2-yl)-1,3,4-oxadiazole (L1)(1, 3), 2-(pyridin-2-yl)-5-p-tolyl-1,3,4-oxadiazole (L2) (2, 4), have been successfully synthesized and characterized by elemental analysis, H-1 NMR and IR spectra. X-ray crystal structure analysis has been carried out on 1, 2 and 3. Photoluminescence properties of 2 are unique in three respects: (1) an obvious emission blue shift, (2) a high quantum yield (0.94) comparing with the other three complexes (<0.03), and (3) a longer excited state lifetime than those of the others. Systematic analysis suggests that its drastic enhancement in photoluminescence performances is triggered by the extraordinary rigid pseudo sandwich structure constructed from strong intra- and inter-molecular pi-pi stacking interactions in its crystal structure. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.02.020

文献信息

• Photophysical performance comparison between bulk Cu(I) complex and its electrospinning fibers: Synthesis and characterization
  作者：Wan Pu、Zhao Yuqing、Wang Lisha

  DOI：10.1016/j.saa.2016.06.017

  日期：2016.12

  owned a mixed character of metal-to-ligand-charge-transfer which suffered from bad geometric relaxation. To limit this geometric relaxation and improve emissive performance, this Cu(I) complex was doped into a polymer host through electrospinning technique. Photophysical comparison between solid state sample, solution sample and composite samples indicated that excited state geometric relaxation was effectively

  在该报告中，设计了在其共轭平面上具有电子牵引基团的二胺配体。甲基与该二胺配体连接，希望进一步增加其空间位阻。合成了其Cu（I）配合物，并通过NMR，单晶分析和光物理分析对其进行了表征。该Cu（I）配合物中存在扭曲的四面体配位场。其开始的电子跃迁具有金属到配体电荷转移的混合特性，该特性遭受不良的几何弛豫。为了限制这种几何弛豫并提高发射性能，通过电纺丝技术将此Cu（I）配合物掺入了聚合物主体中。固态样品之间的光物理比较
• Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds <i>via</i> sp³ C–H functionalization of azaarenes
  作者：Geeta Sai Mani、Kavitha Donthiboina、Nagula Shankaraiah、Ahmed Kamal

  DOI：10.1039/c9nj03573g

  日期：——

  for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole scaffolds has been developed via sp3 C–H functionalization. Gratifyingly, this method involves oxidative amination with concomitant base-mediated cyclization of methylhetarenes and acylhydrazines by employing iodine and Cs2CO3. The key features of the present method include good functional group tolerance, a clean protocol, metal-free conditions

  通过sp 3 C–H官能化开发了一种有效的碘介导的一锅合成方案，用于合成2,5-二取代的1,3,4-恶二唑支架。令人欣慰的是，该方法涉及通过使用碘和Cs 2 CO 3进行氧化胺化反应，并伴随碱介导的甲基戊烯和酰基肼的环化反应。本方法的关键特征包括良好的官能团耐受性，清洁的方案，无金属的条件和高收率，使得该方案成为合成生物活性分子及其关键构件的有吸引力的策略。
• Molecular Logic Gates and Switches Based on 1,3,4-Oxadiazoles Triggered by Metal Ions
  作者：Ai-Fang Li、Yi-Bin Ruan、Qian-Qian Jiang、Wen-Bin He、Yun-Bao Jiang

  DOI：10.1002/chem.200903265

  日期：2010.5.17

  chelating environment for metal ions. These compounds showed fluorescence response profiles varying in both emission intensity and wavelength toward the tested metal ions Ni2+, Cu2+, Zn2+, Cd2+, Hg2+, and Pb2+ and the responses were dependent on the substituent X, with those of 1 d being the most substantial. The 1,3,4‐oxadiazole O or N atom and pyridine N atom were identified as metal‐chelating sites. The

  用于信息处理应用程序的有机分子设备是构建分子级机器的高度有用的构建基块。能够执行逻辑运算的“智能”分子的发展将使分子级设备和机器的创建成为可能。我们设计了一系列带有2-（对位取代）苯基和5-（邻吡啶基）基团的2,5-二芳基-1,3,4-恶二唑（取代基X = NMe 2，OEt，Me，H和Cl; 1 a – e）形成金属离子的双齿螯合环境。这些化合物对被测金属离子Ni 2 +，Cu 2 +，Zn的荧光响应曲线在发射强度和波长上均发生变化。2+，Cd 2 +，Hg 2+和Pb 2+以及响应取决于取代基X，最重要的是1 d。1,3,4-恶二唑O或N原子和吡啶N原子被确定为金属螯合位点。金属螯合后1 d的荧光响应被用于开发OR，NOR，INHIBIT和EnNOR逻辑门以及“ ON-OFF-ON”和“ OFF-ON-OFF”荧光开关的真值表。 ，3,4-恶二唑分子系统。
• Study on polymer fibers doped with phosphorescent Re(I) complex via electrospinning: Synthetic strategy, structure, morphology and photophysical features
  作者：Wang Dejin、Liu Qiang、Wang Fei

  DOI：10.1016/j.saa.2013.11.022

  日期：2014.3

  ligands made the Re(I) complex molecules adjust a highly ordered arrangement which was positive to improve emissive performance. In order to repress the excited state geometric relaxation and further improve the emissive performance, the Re(I) complex was doped into a polymer host poly(vinylpyrrolidone) via electrospinning, resulting in composite fibers. The morphology of those composite fibers was analyzed

  在以下论文中，合成了在其二胺配体（表示为NN）中具有吸电子恶二唑基团的Re（I）配合物。其单晶结构分析证实了配体和配合物的成功合成。中心Re离子位于传统的八面体配位环境中。二胺配体2-（吡啶-2-基）-5-（对甲苯基）-1,3,4-恶二唑（表示为PPOZ）具有共面结构，并且相应的面对面π-π吸引PPOZ配体使Re（I）复杂分子调整了高度有序的排列，这对改善发射性能是积极的。为了抑制激发态的几何弛豫并进一步改善发射性能，通过电纺丝将Re（I）配合物掺入聚合物主体聚乙烯吡咯烷酮中，得到复合纤维。通过电子显微镜分析那些复合纤维的形态。散装样品和复合纤维之间的光物理比较表明，复合纤维显示出发射蓝移，更长的激发态寿命和改善的光稳定性。进一步的分析表明，当将Re（I）络合物分子固定在聚合物基质中时，可以有效地抑制激发态的几何弛豫，从而导致上述变化。
• Synthesis, characterization, crystal structures, and photophysical properties of a series of room-temperature phosphorescent copper(I) complexes with oxadiazole-derived diimine ligand
  作者：Fuxiang Wei、L. Fang、Y. Huang

  DOI：10.1016/j.ica.2010.04.041

  日期：2010.8

  paper, we report four phosphorescent Cu(I) complexes of [Cu(OP)(PPh 3 ) 2 ]BF 4 , [Cu(Me-OP)(PPh 3 ) 2 ]BF 4 , [Cu(OP)(POP)]BF 4 , and [Cu(Me-OP)(POP)]BF 4 with oxadiazole-derived diimine ligands, where OP = 2-(5-phenyl-[1,3,4]oxadiazol-2-yl)-pyridine, Me-OP = 2-(5-p-tolyl-[1,3,4]oxadiazol-2-yl)-pyridine, POP = bis(2-(diphenylphosphanyl)phenyl) ether, and PPh 3 = triphenylphosphane, including their

  摘要本文报道了[Cu（OP）（PPh 3）2] BF 4，[Cu（Me-OP）（PPh 3）2] BF 4，[Cu（OP） （POP）] BF 4和具有恶二唑衍生的二亚胺配体的[Cu（Me-OP）（POP）] BF 4，其中OP = 2-（5-苯基-[1,3,4]恶二唑-2-基）-吡啶，Me-OP = 2-（5-对甲苯基-[1,3,4]恶二唑-2-基）-吡啶，POP =双（2-（2-（二苯基膦基）苯基）醚，PPh 3 =三苯基膦，包括其合成，晶体结构，光物理性质和电子性质。Cu（I）中心在Cu（I）配合物中具有扭曲的四面体几何形状。理论计算表明，所有发射均源于三重态金属向配体电荷转移的激发态。