[1,3,4-oxadiazole-2,5-diylbis(4,1-phenylenemethylene)]bisphosphonic acid tetraethyl ester | 58370-38-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: [1,3,4-oxadiazole-2,5-diylbis(4,1-phenylenemethylene)]bisphosphonic acid tetraethyl ester
• 英文别名: diethyl 4-(5-(4-((diethoxyphosphino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)benzylphosphonate；2,5-Bis[4-[[diethoxy(oxido)phosphaniumyl]methyl]phenyl]-1,3,4-oxadiazole；2,5-bis[4-[[diethoxy(oxido)phosphaniumyl]methyl]phenyl]-1,3,4-oxadiazole
• CAS: 58370-38-0
• 化学式: C₂₄H₃₂N₂O₇P₂
• 分子量: 522.475
• InChiKey: GSQLDZGNXGLQJE-UHFFFAOYSA-N

物化性质

• 熔点：
  136-138 °C(Solvent: Ethyl acetate ; Diethyl ether)
• 沸点：
  654.2±65.0 °C(Predicted)
• 密度：
  1.221±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [1,3,4-oxadiazole-2,5-diylbis(4,1-phenylenemethylene)]bisphosphonic acid tetraethyl ester 、 N,N-二乙基-4-氨基苯甲醛 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 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：

  对甲苯甲酰肼 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 [1,3,4-oxadiazole-2,5-diylbis(4,1-phenylenemethylene)]bisphosphonic acid tetraethyl ester
  参考文献：
  名称：

  New Heterocycle-Based Organic Molecule with Two-Photon Induced Blue Fluorescent Emission

  摘要：

  我们合成了一种新的基于杂环的四极分子，它以 2,5-二苯基-1,3,4-恶二唑为π中心，两个咔唑为末端单元。在波长为 788 纳米时，它呈现出双光子诱导的蓝色发射，其飞秒区的双光子吸收截面测量值为 239 × 10-50 cm4 s 光子-1。

  DOI：

  10.1071/ch05179

文献信息

• Multipolar symmetric and asymmetric N–heterocyclic compounds with efficient two−photon absorption
  作者：Zhi-Bin Cai、Li Bai、Yu-Lu Pan、Fei-Fei Ma、Sheng-Li Li、Yu-Peng Tian

  DOI：10.1016/j.jphotochem.2017.05.025

  日期：2017.9

  designed and synthesized. Their structures were characterized by Fourier transform infrared spectroscopy, hydrogen−1 nuclear magnetic resonance, and mass spectrometry. Their photophysical properties including linear absorption, single–photon excited fluorescence, two–photon absorption, and two–photon excited fluorescence, were systematically investigated in various solvents. The relationships between the

  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。
• 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 efficient solid-state emission of conjugated donor–acceptor–donor triphenylamine chromophores
  作者：Binbin Wang、Ying Qian

  DOI：10.1039/c3nj41115j

  日期：——

  Two symmetrical donor–acceptor–donor chromophores built by connecting two triphenylamine donors to a central electron acceptor 2,5-diphenyl-1,3,4-oxadiazole or anthracene core have been synthesized and characterized. The aggregation-induced emission phenomenon of these compounds with bright and deep emission from orange to green in the solid state can be obsreved. The chromophores based on the triphenylamine unit exhibit efficient solid-state emission. The results indicate that D–A–D conjugation bridging provides a new opportunity for AIE-materials. The multiphoton induced fluorescence spectra of these chromophores were measured using a femtosecond Ti:sapphire. The three-photon excited fluorescence spectra are in the green region with peaks at 554 nm for An-BIPAS and 504 nm for Ox-BIASP in THF, respectively. These AIE-active compounds are potential materials to design sensitive and selective fluorescent sensors or bioprobes.

  通过将两个三苯胺供体连接到中心电子受体 2,5-二苯基-1,3,4-恶二唑或蒽核，合成了两个对称的供体-受体-受体发色团，并对其进行了表征。可以观察到这些化合物的聚集诱导发射现象，在固态下会发出从橙色到绿色的明亮而深邃的发射。基于三苯胺单元的发色团表现出高效的固态发射。结果表明，DâAâD 共轭桥接为 AIE 材料提供了新的机遇。使用飞秒钛蓝宝石测量了这些发色团的多光子诱导荧光光谱。三光子激发的荧光光谱位于绿色区域，在 THF 中，An-BIPAS 和 Ox-BIASP 的荧光光谱峰值分别为 554 nm 和 504 nm。这些 AIE 活性化合物是设计灵敏和选择性荧光传感器或生物探针的潜在材料。
• 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.