diethyl 1-pyrylphosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: diethyl 1-pyrylphosphonate
• 英文别名: diethyl pyren-1-ylphosphonate；1-Diethoxyphosphorylpyrene
• 化学式: C₂₀H₁₉O₃P
• 分子量: 338.343
• InChiKey: BETZQBGNKJNEOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl 1-pyrylphosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到1-pyrylphosphonic acid
  参考文献：
  名称：

  Two-Dimensional Self-Assembly of 1-Pyrylphosphonic Acid:  Transfer of Stacks on Structured Surface

  摘要：

  Strong hydrogen bonding and pi-pi stacking between 1-pyrylphosphonic acid (PYPA) molecules were exploited to create self-assembled two-dimensional supramolecular structures. Polycrystalline films of these laminate crystalline PYPA bilayers; were easily deposited onto the solid supports through a simple spin-coating technique. Atomic force microscopy (AFM), scanning tunneling microscopy (STM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), UV-vis absorption, and fluorescence spectroscopy reveal that processing parameters, such as solvent, concentration, and surface of the substrate, are critical factors in determining the final morphology of the stacked film. Robust laminate structures could be obtained only when short alkyl chain protic solvents (methanol or ethanol) and a nonhydrophobic substrate surface were used. Polycrystalline films were formed through the nucleation and growth of PYPA molecules into laminate structures at the air/solvent interface before they land on the substrate during the spin-coating process. These films possess good mechanical properties and were easily transferred onto a SiO2/Si substrate that was patterned with Au electrodes without breaking their crystalline structures. The successful transfer of the laminate crystals allows us to probe their electrical properties through a field effect transistor device. A gating effect on the charge transport of the stacked films indicates that PYPA laminate crystal possesses p-typed semiconductor characteristics.

  DOI：

  10.1021/ja0563152
• 作为产物：
  描述：

  1-溴芘 、 氯磷酸二乙酯 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 2.0h， 以75%的产率得到diethyl 1-pyrylphosphonate
  参考文献：
  名称：

  Two-Dimensional Self-Assembly of 1-Pyrylphosphonic Acid:  Transfer of Stacks on Structured Surface

  摘要：

  Strong hydrogen bonding and pi-pi stacking between 1-pyrylphosphonic acid (PYPA) molecules were exploited to create self-assembled two-dimensional supramolecular structures. Polycrystalline films of these laminate crystalline PYPA bilayers; were easily deposited onto the solid supports through a simple spin-coating technique. Atomic force microscopy (AFM), scanning tunneling microscopy (STM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), UV-vis absorption, and fluorescence spectroscopy reveal that processing parameters, such as solvent, concentration, and surface of the substrate, are critical factors in determining the final morphology of the stacked film. Robust laminate structures could be obtained only when short alkyl chain protic solvents (methanol or ethanol) and a nonhydrophobic substrate surface were used. Polycrystalline films were formed through the nucleation and growth of PYPA molecules into laminate structures at the air/solvent interface before they land on the substrate during the spin-coating process. These films possess good mechanical properties and were easily transferred onto a SiO2/Si substrate that was patterned with Au electrodes without breaking their crystalline structures. The successful transfer of the laminate crystals allows us to probe their electrical properties through a field effect transistor device. A gating effect on the charge transport of the stacked films indicates that PYPA laminate crystal possesses p-typed semiconductor characteristics.

  DOI：

  10.1021/ja0563152

文献信息

• Preparation of Arylphosphonates by Palladium(0)-Catalyzed Cross-Coupling in the Presence of Acetate Additives: Synthetic and Mechanistic Studies
  作者：Marcin Kalek、Martina Jezowska、Jacek Stawinski

  DOI：10.1002/adsc.200900590

  日期：2009.12

  arylphosphonate diesters via a palladium-catalyzed cross-coupling of H-phosphonate diesters with aryl electrophiles, promoted by acetate ions, was developed. A significant shortening of the cross-coupling time in the presence of the added acetate ions was achieved for bidentate and monodentate supporting ligands, and for different aryl electrophiles (iodo, bromo and triflate derivatives). The reaction conditions

  一种有效的协议，用于arylphosphonate二酯的合成通过钯催化的交叉偶联芳基亲电子，由乙酸根离子促进H-膦酸二酯的，被开发。对于二齿和单齿支持配体以及不同的芳基亲电子试剂（碘，溴和三氟甲磺酸酯衍生物），在添加乙酸根离子的情况下，交叉偶联时间大大缩短。根据催化剂的量，支持的配体和所用乙酸根离子的来源对反应条件进行了优化。使用这种新开发的方案可以合成各种芳基膦酸酯，包括具有潜在生物学意义的芳基膦酸酯。还讨论了所研究反应的一些机理方面。
• Regioselective Synthesis of 2- or 2,7-Functionalized Pyrenes via Migration
  作者：Liqi Qiu、Wei Hu、Di Wu、Zheng Duan、Francois Mathey

  DOI：10.1021/acs.orglett.8b03270

  日期：2018.12.21

  simple method for the preparation of 2- or 2,7-functional pyrenes from 1- or 1,6-substituted derivatives is reported. The synthesis involves the unexpected 1,2-phosphinyl migration in an AlCl3/NaCl melt. The structure of the product has been unambiguously confirmed by X-ray crystallography. We also demonstrated that further functionalization of pyrene through C–P bond activation is possible. These 2,7-positions

  报道了一种由1-或1，6-取代的衍生物制备2-或2，7-官能pyr的简单方法。合成过程涉及AlCl 3 / NaCl熔体中意外的1,2-亚膦酰基迁移。通过X射线晶体学已明确证实了产物的结构。我们还证明了through通过C-P键活化的进一步功能化是可能的。否则，很难推导这2，7位。
• Two-Dimensional Self-Assembly of 1-Pyrylphosphonic Acid:  Transfer of Stacks on Structured Surface
  作者：Hin-Lap Yip、Hong Ma、Alex K.-Y. Jen、Jianchun Dong、Babak A. Parviz

  DOI：10.1021/ja0563152

  日期：2006.5.1

  Strong hydrogen bonding and pi-pi stacking between 1-pyrylphosphonic acid (PYPA) molecules were exploited to create self-assembled two-dimensional supramolecular structures. Polycrystalline films of these laminate crystalline PYPA bilayers; were easily deposited onto the solid supports through a simple spin-coating technique. Atomic force microscopy (AFM), scanning tunneling microscopy (STM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), UV-vis absorption, and fluorescence spectroscopy reveal that processing parameters, such as solvent, concentration, and surface of the substrate, are critical factors in determining the final morphology of the stacked film. Robust laminate structures could be obtained only when short alkyl chain protic solvents (methanol or ethanol) and a nonhydrophobic substrate surface were used. Polycrystalline films were formed through the nucleation and growth of PYPA molecules into laminate structures at the air/solvent interface before they land on the substrate during the spin-coating process. These films possess good mechanical properties and were easily transferred onto a SiO2/Si substrate that was patterned with Au electrodes without breaking their crystalline structures. The successful transfer of the laminate crystals allows us to probe their electrical properties through a field effect transistor device. A gating effect on the charge transport of the stacked films indicates that PYPA laminate crystal possesses p-typed semiconductor characteristics.