methyl (3-(pyren-1-yl)propyl)carbamate | 1242281-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: methyl (3-(pyren-1-yl)propyl)carbamate
• CAS: 1242281-24-8
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: FZLJMIPYJGBXEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl (3-(pyren-1-yl)propyl)carbamate 在 sodium hydroxide 、 盐酸 作用下， 以 丙醇 、 水 为溶剂， 反应 14.0h， 以22%的产率得到3-(pyren-1-yl)propan-1-ammonium chloride
  参考文献：
  名称：

  ‘Remote’ Adiabatic Photoinduced Deprotonation and Aggregate Formation of Amphiphilic N-Alkyl-N-methyl-3-(pyren-1-yl)propan-1-ammonium Chloride Salts

  摘要：

  The absorption and emission properties of a series of amphiphilic N-alkyl-N-methyl-3-(pyren-1-yl)propan-1-ammonium chloride salts were investigated in solvents of different polarities and over a wide concentration range. For example, at 10(-5) M concentrations in tetrahydrofuran (THF), salts with at least one N-H bond exhibited broad, structureless emissions even though time-correlated single photon counting (TCSPC) experiments indicated negligible static or dynamic intermolecular interactions. Salts with a butylene spacer or lacking an N-H bond showed no discernible structureless emission; their emission spectra were dominated by the normal monomeric fluorescence of a pyrenyl group and the TCSPC histograms could be interpreted on the basis of intramolecular photophysics. The broad, structureless emission is attributed to an unprecedented, rapid, adiabatic proton-transfer to the medium, followed by the formation of an intramolecular exciplex consisting of amine and pyrenyl groups. The proposed mechanism involves excitation of a ground-state conformer of the salts in which the ammonium group sits over the pyrenyl ring due to electrostatic stabilization. At higher concentrations, with longer N-alkyl groups, or in selected solvents, electronic excitation of the salts led to dynamic and static excimeric emissions. For example, whereas the emission spectrum of 10(-3) M N-hexyl-N-methyl-3-(pyren-1-yl)propan-1-ammonium chloride in THF consisted of comparable amounts of monomeric and excimeric emission, the emission from 10(-5) M N-dodecyl-N-methyl-3-(pyren-1-yl)propan-1-ammonium chloride in 1:9 (v:v) ethanol/water solutions was dominated by excimeric emission, and discrete particles near micrometer size were discernible from confocal microscopy and dynamic light scattering experiments. Comparison of the static and dynamic emission characteristics of the particles and of the neat solid of N-dodecyl-N-methyl-3-(pyren-1-yl)propan-1-ammonium chloride indicate that molecular packing in the microparticles and in the single crystal are very similar if not the same. It is suggested that other examples of the adiabatic proton transfer found in the dilute concentration regime with the pyrenyl salts may be occurring in very different systems, such as in proteins where conformational constraints hold ammonium groups over aromatic rings of peptide units.

  DOI：

  10.1021/ja208674s
• 作为产物：
  描述：

  4-(1-芘基)丁酰胺 在 溴 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl (3-(pyren-1-yl)propyl)carbamate
  参考文献：
  名称：

  聚（甲基丙烯酸烷基酯）的温度和烷基对on客体分子激发单线态的分子间和分子内相互作用的影响

  摘要：

  温度引起的pyr和N，N荧光的静态和动态特性变化-二甲基-3-（吡喃-1-基）丙-1-胺（PyC3NMe2）已用于确定由5种聚甲基丙烯酸烷基酯（PAMA）聚合物薄膜提供的各向异性环境中这些探针的位置和迁移率其中烷基是乙基，丁基，异丁基，环己基和十六烷基。from的发射报告了客体位点的极性以及分子在位点之间平移扩散的能力，而PyC3NMe2的发射则产生了有关客体位点的流动性和形状的信息。已从20到> 400 K获得数据，该范围跨越宿主体内数个松弛过程的开始。这些数据表明the烯基在大多数PAMA中位于酯官能团附近，尽管与它们（和主链）的距离取决于烷基的体积。这项研究得出的最重要的结论之一是，探针分子附近的节段弛豫现象的发生率（而不是自由体积（如先前从聚乙烯薄膜中的荧光测量得出的结论））是导致荧光变化的主要因素。实际上重要的是，这些速率的变化已允许定位在探针附近发生的许多松弛现象的开始温度。

  DOI：

  10.1021/jp105461r