2,5-bis(4-ethynylphenyl)-[1,3,4]oxadiazole | 817171-72-5

• 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-ethynylphenyl)-[1,3,4]oxadiazole
• 英文别名: 2,5-Bis(4-ethynylphenyl)-1,3,4-oxadiazole；2,5-bis(4-ethynylphenyl)-1,3,4-oxadiazole
• CAS: 817171-72-5
• 化学式: C₁₈H₁₀N₂O
• 分子量: 270.29
• InChiKey: PRTCIELAKJHEJP-UHFFFAOYSA-N

物化性质

• 熔点：
  196.1-198.0 °C (decomp)
• 沸点：
  425.4±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  氯化甲基汞 、 2,5-bis(4-ethynylphenyl)-[1,3,4]oxadiazole 在 NaOH 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以76%的产率得到
  参考文献：
  名称：

  2,5-双(乙炔基苯基)-1,3,4-恶二唑衍生的双核金(I)和汞(II)配合物的合成、结构和光物理

  摘要：

  摘要 研究了二炔配体 2,5-双(乙炔基苯基)-1,3,4-恶二唑与金 (I) 和汞 (II) 盐的有机金属化学。四种新的第 11 组金（I）和第 12 组汞（II）双（炔基）双核配合物用缺电子恶二唑 (OXD) 间隔基 [(PR3)AuC C(p-C6H4)(OXD)(p-C6H4) 功能化C CAu(PR3)] (R = Ph, 1; Me, 2) 和 [RHgC C(p-C6H4)(OXD)(p-C6H4)C CHgR] (R = Ph, 3; Me, 4)在室温下，通过相应的金属氯化物前体与 HC C(p-C6H4)(OXD)(p-C6H4)C CH 的碱催化脱卤化氢反应，产率良好。我们报告了这些金属烯的光吸收和光致发光特性。已通过 X 射线晶体学研究了 1 的结构特性，其中没有观察到短接触的亲热相互作用。系统地表征了重金属原子对这些金属炔基系统中从 S1 单线态激发态到 T1 三

  DOI：

  10.1016/j.molstruc.2008.03.003
• 作为产物：
  描述：

  2,5-双(4-溴苯基)-1,3,4-恶二唑 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2,5-bis(4-ethynylphenyl)-[1,3,4]oxadiazole
  参考文献：
  名称：

  甲硅烷基间距的交替供体-受体二乙烯基芳烃共聚物中的链内能量转移。

  摘要：

  甲硅烷基间隔的供体-受体二乙烯基芳烃共聚物是通过将双炔7与双乙烯基硅烷3进行硅氢加成而合成的；在供体-受体生色团之间观察到有效的链内能量转移。

  DOI：

  10.1039/b206308e

文献信息

• Synthesis, Characterization, Luminescence, and Non-linear Optical Properties of Oxadiazole- and Truxene-Containing Platinum(II) Alkynyl Complexes with Donor−Acceptor Functionalities
  作者：Carmen Ka Man Chan、Chi-Hang Tao、Hoi-Lam Tam、Nianyong Zhu、Vivian Wing-Wah Yam、Kok-Wai Cheah

  DOI：10.1021/ic8017979

  日期：2009.4.6

  A series of luminescent platinum(II) alkynyl complexes containing 2,5-diphenyl-1,3,4-oxadiazole (oxa-2,5) and 10,15-dihydro-5H-diindeno[1,2-a;1′,2′-c]fluorene (truxene) as the cores and different electron donors at the periphery has been synthesized and characterized. These complexes showed long-lived emissions in both solution and in the solid state at room temperature and have been found to exhibit

  一系列含有2,5-二苯基-1,3,4-恶二唑（oxa-2,5）和10,15-dihydro-5 H -diindeno [1,2- a ; 1的发光铂（II）炔基配合物。合成并表征了以'，2'- c ]芴（truxene）为核，并在外围形成了不同的电子给体。这些络合物在室温下在溶液和固态下均表现出长寿命的发射，并且发现具有双光子吸收（2PA）和双光子诱导的发光。其2PA横截面（σ 2）也已被确定。
• Highly efficient blue electrophosphorescent devices with a new series of host materials: polyphenylene-dendronized oxadiazole derivatives
  作者：Shiyan Chen、Xinjun Xu、Yunqi Liu、Wenfeng Qiu、Gui Yu、Xiaobo Sun、Hengjun Zhang、Ting Qi、Kun Lu、Xike Gao、Ying Liu、Daoben Zhu

  DOI：10.1039/b705515c

  日期：——

  A new series of oxadiazole derivatives TPO, PPO, MTPO, MPPO, BTPO, and BPPO have been designed and synthesized in high yields by a convenient synthetic procedure. A single crystal structure of TPO exhibited that this polyphenylene-dendronized material has a sterically crowded structure which efficiently prevents π–π stacking and endows it with good thermal stability. The photophysical properties of the materials show strong emission between 376 and 390 nm in the films. In addition, good reversible reductive waves in the cyclic voltammograms implied that these materials might have good electron transport properties. Blue electrophosphorescent devices fabricated using these materials as the host materials and iridium(III)bis[4,6-di-fluorophenyl-pyridinato-N,C2′]picolinate as the blue phosphorescent dopant emitter show very high efficiencies. A maximum luminance of 4484 cd m−2 and an external quantum efficiency of 6.20% were achieved under ambient conditions.

  一系列新的氧杂二唑衍生物TPO、PPO、MTPO、MPPO、BTPO和BPPO已经通过一种方便的合成方法设计并合成，且产率很高。TPO的单晶结构显示出该聚苯甲烯树枝状材料具有立体拥挤的结构，这有效地阻止了π–π堆积，并赋予其良好的热稳定性。材料的光物理性质显示，在薄膜中在376到390 nm之间有强烈的发射。此外，循环伏安图中良好的可逆还原波表明这些材料可能具有良好的电子传输性能。使用这些材料作为主材料，铱(III)双[4,6-二氟苯基-吡啶-N,C2']皮克林酸盐作为蓝色磷光掺杂发射体制造的蓝色电致磷光器件表现出非常高的效率。在环境条件下，达到了4484 cd m−2的最高亮度和6.20%的外量子效率。
• Tuning the photophysical properties of carboranyl luminophores by <i>closo</i>- to <i>nido</i>-carborane conversion and application to OFF–ON fluoride sensing
  作者：Nguyen Van Nghia、Jihun Oh、Surendran Sujith、Jaehoon Jung、Min Hyung Lee

  DOI：10.1039/c8dt03771j

  日期：——

  Conversion of poorly emissive closo-carboranyl luminophores to nido-derivatives gave rise to strong emission, allowing the selective OFF–ON fluorescence sensing of fluoride.

  将发射性较差的closeno-carboranyl发光体转化为nido-衍生物可产生较强的发射，从而实现对氟化物的选择性OFF-ON荧光传感。
• Reversible Photoactivated Phosphorescence of Gold(I) Arylethynyl Complexes in Aerated DMSO Solutions and Gels
  作者：Shigang Wan、Wei Lu

  DOI：10.1002/anie.201610762

  日期：2017.2.6

  Phosphorescence in fluid solutions at ambient temperature is usually quenched by molecular oxygen via energy transfer, and singlet oxygen is concomitantly sensitized. The long‐lived phosphorescence of a series of AuI arylethynyl complexes with tunable emission energies in aerated dimethyl sulfoxide (DMSO) solutions can be completely and repeatedly switched on by controlled photoirradiation. A trace

  室温下流体溶液中的磷光通常通过分子氧通过能量转移来淬灭，并且单线态氧同时被敏化。充气二甲基亚砜（DMSO）溶液中具有可调发射能量的一系列Au I芳基乙炔基络合物的长寿命磷光可以通过控制光辐照完全重复地打开。有人提出了光敏单线态氧对痕量的DMSO的氧化作用，从而导致在光活化过程中Au I荧光粉的局部微环境中分子氧的消耗。利用光活化的磷光并使用紫外线作为非接触笔，已使用含有Au I的DMSO凝胶演示了书写-擦除-重写原型。 芳基乙炔基络合物。
• Organometallic Coordination Polymers Generated from Bent Bis(acetylenylphenyl)oxadiazole Ligands and Ag(I) Salts
  作者：Yu-Bin Dong、Qiang Zhang、Le Wang、Jian-Ping Ma、Ru-Qi Huang、Da-Zhong Shen、De-Zhan Chen

  DOI：10.1021/ic0508223

  日期：2005.9.1

  Two new bent oxadiazole bridging benzoacetylene ligands 2,5-bis(4-ethynylphenyl)-1,3,4-oxadiazole (L9) and 2,5bis(3-ethynylphenyl)-1,3,4-oxadiazole (L10) were synthesized. The coordination chemistry of them with various inorganic Ag(I) salts has been investigated. Seven new coordination polymers were prepared by solution reactions and fully characterized by infrared spectroscopy, elemental analysis, and single-crystal X-ray diffraction. [Ag-2(L9)]-(SO3CF3)(2) (1) (triclinic, P (1) over bar; a = 10.292(4), b = 10.794(4), c = 11.399(5) angstrom; alpha = 98.894(5), beta = 102.360(6), gamma = 90.319(5)degrees; Z = 2), [Ag(L9)]SbF6 (2) (orthorhombic, Cmca; a = 19.059(9), b 12.922(6), c 15.609(7) angstrom; Z = 8), [Ag(L9)]BF4 (3) (orthorhombic, Cmca; a = 19.128(3), b 12.6042(18), c 28.003(4) angstrom; Z = 16), [Ag(L9)]CIO4 (4) (monoclinic, P2(1)/c; a = 8,5153(16), b = 19.722(4), c 10.320(2) angstrom; beta = 105.307(3)degrees; Z = 4), [Ag(L10)]-SO3CF3 (5) (triclinic, P (1) over bar; a = 9.0605(13), b = 10.4956(15), c = 10.8085(16) angstrom; alpha = 101.666(2), beta = 109,269(2), gamma = 100.944(2)0; Z = 2), [Ag(L10)(H2O)(0.5)]BF4-0.5H(2)O (6) (monoclinic, C2/m; a = 32.180(6), b = 17.027(3), c = 8.1453(15) angstrom; beta = 102.541(3)degrees; Z = 8), and [Ag-2(L10)(2)(H2O)](CIO4)(2)}-o-xylene (7) (monoclinic, P2(1)/c; a = 8.1460(10), b = 17.326(2), c = 30.345(4) angstrom; beta = 97.71 degrees; Z = 4) were obtained by the combination of L9 and L10 with various Ag(I) salts in a benzene/methylene chloride mixed solvent system. In addition, the luminescent and electrical conductive properties of these new compounds were investigated.