N1-(1-pyrenylmethyl)acetamide | 263237-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N1-(1-pyrenylmethyl)acetamide
• 英文别名: N-Acetyl-1-aminomethylpyrene；1-(acetamidomethyl)pyrene；N-(pyren-1-ylmethyl)acetamide；N-(Pyren-1-Ylmethyl)acetamide
• CAS: 263237-56-5
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: IGDIETIXWIPXQF-UHFFFAOYSA-N

物化性质

• 沸点：
  555.8±29.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  舒洛芬 、 N1-(1-pyrenylmethyl)acetamide 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到N1-(1-pyrenylmethyl)-2-[4-(2-thienylcarbonyl)phenyl]propanamide
  参考文献：
  名称：

  Pyrene-benzoylthiophene bichromophores as selective triplet photosensitizers

  摘要：

  芘和苯甲酰噻吩单元的组合是设计双色光敏剂的一种有趣方法，这种光敏剂具有更高的系统间交叉量子产率和更强的选择性。本研究利用一个光异构化反应模型说明了这一策略的潜力。

  DOI：

  10.1039/b510880b
• 作为产物：
  描述：

  芘-1-基甲胺 、 乙酸酐 以 乙腈 为溶剂， 反应 20.0h， 以89%的产率得到N1-(1-pyrenylmethyl)acetamide
  参考文献：
  名称：

  Probing Intermolecular Communication with Surface-Attached Pyrene

  摘要：

  We report on the covalent attachment of pyrene derivatives to solid substrates and their spectroscopic and electrochemical characterization. We have constructed several molecular assemblies attached to silica and indium-doped tin oxide surfaces where pyrene molecules are co-immobilized with other functionalities. It was shown that the addition of hydrophobic molecules to the pyrene-containing interface results in a significant decrease in the pyrene I-1/I-3 vibronic emission band ratio and an increase in the water drop contact angle due to increased hydrophobicity of the interface. The co-attachment of perylenedodecanoic acid, for which the absorption band overlaps with the emission spectrum of pyrene, shows significant intermolecular communication between these species. The co-immobilization of ferrocene serves as an effective fluorescence quencher for tethered pyrene. In all cases, our data point to significant intermolecular communication between adsorbate species, and the combination of spectroscopic and electrochemical interrogation provides insight into the loading density and local environinent(s) characteristic of these interfaces.

  DOI：

  10.1021/jp045323m

文献信息

• Synthesis and Photophysics of a 1-Pyrenylmethyl-Substituted 2‘-Deoxyuridine-5-Carboxamide Nucleoside:  Electron-Transfer Product Lifetimes and Energies
  作者：Charles E. Kerr、C. Denise Mitchell、Yun-Ming Ying、Bruce E. Eaton、Thomas L. Netzel

  DOI：10.1021/jp993776z

  日期：2000.3.1

  This paper presents results of the synthesis and photophysical study of N-(1-pyrenylmethyl)-2'-deoxyuridine-5-carboxamide (PMA-dU) and its spectroscopic model N-acetyl-1-aminomethylpyrene (PMA-Ac). The goal in these studies is to learn about the intrinsic forward and reverse electron-transfer (ET) processes in the PMA-dU nucleoside as a means of developing pyrenyl-dU nucleosides with ET product lifetimes in the 0.5 ns time range. Absorbance and emission spectra, emission quantum yields, and emission lifetimes are reported for both compounds in three solvents. The data show that the emission yield quenching varies from 75 to 98% in the solvent series THF, MeCN, and MeOH. Pyrenyl (pi,pi*)(1) emission quenching is assigned to ET that forms the pyrene(.)+/dU(.-) product as observed previously in other pyrenyl-dU nucleosides. In contrast to the monoexponential emission decay of PMA-Ac, the emission of PMA-dU at all wavelengths is multiexponential with 4 lifetimes in THF and nearly always with 3 in McCN and MeOH. The multiexponential decay is likely due to the presence of multiple nucleoside conformers. Importantly, the emission decay for the nucleoside in the 500-550 nm region is assigned to relaxation of the pyrene(.+)/dU(.-) ET product. The 0.5-4 ns time range contains over 95% of the emission amplitude in this wavelength region for the polar solvents MeCN and MeOH. Thus, the ET product in PMA-dU appears to have the desired long lifetime. Additionally, CIS INDO/S computations of the excited-state properties of 19 conformers of the nucleoside model N-(1-pyrenylmethyl)-1-methyluracil-5-carboxamide (PMA-U-Me) identify two key factors that control the energy of pyrene(.+)/dU(.-) ET products. One is ease of reduction of the uracil subunit, in turn controlled by variation of the angle between the uracil-C5 carbonyl and the plane of uracil (R = 0.90). The other is Coulombic attraction between the pyrenyl cation and uracil anion subunits. The Coulombic and CO/U-Me dihedral angle contributions to the energy of the ET1 state are independent of each other and can operate either in or out of phase with respect to varying energy of the ET1 state.
• Pyrene-benzoylthiophene bichromophores as selective triplet photosensitizers
  作者：Julia Pérez-Prieto、Lourdes Pastor Pérez、María González-Béjar、Miguel A. Miranda、Salah-Eddine Stiriba

  DOI：10.1039/b510880b

  日期：——

  Combination of the pyrene and benzoylthiophene units constitutes an interesting approach to design bichromophoric photosensitizers with increased intersystem crossing quantum yield and enhanced selectivity. The potential of this strategy has been illustrated in the present work by using a model photoisomerization reaction.

  芘和苯甲酰噻吩单元的组合是设计双色光敏剂的一种有趣方法，这种光敏剂具有更高的系统间交叉量子产率和更强的选择性。本研究利用一个光异构化反应模型说明了这一策略的潜力。
• Probing Intermolecular Communication with Surface-Attached Pyrene
  作者：Maciej Mazur、G. J. Blanchard

  DOI：10.1021/jp045323m

  日期：2005.3.1

  We report on the covalent attachment of pyrene derivatives to solid substrates and their spectroscopic and electrochemical characterization. We have constructed several molecular assemblies attached to silica and indium-doped tin oxide surfaces where pyrene molecules are co-immobilized with other functionalities. It was shown that the addition of hydrophobic molecules to the pyrene-containing interface results in a significant decrease in the pyrene I-1/I-3 vibronic emission band ratio and an increase in the water drop contact angle due to increased hydrophobicity of the interface. The co-attachment of perylenedodecanoic acid, for which the absorption band overlaps with the emission spectrum of pyrene, shows significant intermolecular communication between these species. The co-immobilization of ferrocene serves as an effective fluorescence quencher for tethered pyrene. In all cases, our data point to significant intermolecular communication between adsorbate species, and the combination of spectroscopic and electrochemical interrogation provides insight into the loading density and local environinent(s) characteristic of these interfaces.