1-(1-pyrenyl)-3-N,N-dimethylaminopropane | 85425-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-(1-pyrenyl)-3-N,N-dimethylaminopropane
• 英文别名: N,N-dimethyl-3-(1-pyrenyl)propan-1-amine；N,N-dimethyl-3-(pyren-1-yl)propan-1-amine；PyC3NMe2；N,N-dimethyl-3-pyren-1-ylpropan-1-amine
• CAS: 85425-02-1
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: ZOVSEQUWMFRGKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-pyrenyl)-3-N,N-dimethylaminopropane 在 氢溴酸 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  N，N-二甲基-3-（1-吡啶基）丙烷-1-铵阳离子中分子内，激基介导的，质子耦合的电荷转移过程：阴离子，溶剂极性和温度的影响

  摘要：

  分子内的激基复合物介导的，质子耦合的电荷转移（PCCT）过程已被研究用于一系列N，N在宽温度范围内的低至中等极性的溶剂中，具有不同阴离子（PyS）的-二甲基-3-（1-苯甲酰基）丙-1-铵阳离子。溶剂介导的阳离子构象之间的平衡（使the烯基和铵基团靠近（构象C）或彼此远离）（构象O）以及铵基团以PyS激发单重态绝热转移质子的能力。 。因此，仅在极性相对较低的氢键接受溶剂（四氢呋喃，乙酸乙酯和1,4-二恶烷）中观察到与PCCT过程同时发生的激基复合物发射，而在二氯甲烷中则未观察到。根据激基复合物发射以及其他光谱和热力学数据，PyS（p K）的激发单重态的构象C处的铵基酸度a *）估计为ca。-3.4在四氢呋喃中。激基复合物的发射强度与局部激发态之间的比率（I Ex / I LE）比激基复合物形成和衰减的速率似乎更依赖于阴离子的性质，尽管激发态数据确实如此。没有提供阴离子对C–O平衡的定量影响

  DOI：

  10.1021/acs.jpca.6b01519
• 作为产物：
  描述：

  C₂₂H₂₁NO₂ 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-(1-pyrenyl)-3-N,N-dimethylaminopropane
  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

文献信息

• ‘Remote’ Adiabatic Photoinduced Deprotonation and Aggregate Formation of Amphiphilic <i>N</i>-Alkyl-<i>N</i>-methyl-3-(pyren-1-yl)propan-1-ammonium Chloride Salts
  作者：Shibu Abraham、Richard G. Weiss

  DOI：10.1021/ja208674s

  日期：2011.11.30

  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.
• Photophysics of the intramolecular exciplex formation in .omega.-(1-pyrenyl)-.alpha.-(dimethylamino)alkanes
  作者：A. M. Swinnen、M. Van der Auweraer、F. C. De Schryver、K. Nakatani、T. Okada、N. Mataga

  DOI：10.1021/ja00236a005

  日期：1987.1
• The influence of solvent polarity of the nonradiative decay of exciplexes
  作者：P. Van Haver、N. Helsen、S. Depaemelaere、M. Van der Auweraer、F. C. De Schryver

  DOI：10.1021/ja00018a021

  日期：1991.8

  The efficiency with which the intramolecular exciplex between pyrene and indole or between pyrene and a tertiary amine decays to the locally excited triplet state of pyrene is determined using laser-induced optoacoustic spectroscopy. Upon increasing the solvent polarity, the relative efficiency of this intersystem crossing process decreases compared to the efficiency of the internal conversion process to the singlet ground state. These results can be rationalized in the framework of the Marcus theory. The results obtained by laser-induced optoacoustic spectroscopy are confirmed by transient absorption spectroscopy of the pyrene triplet in the case of the intramolecular exciplex of 1-(1-pyrenyl)3-N,N-dimethylaminopropane.
• Effects of Temperature and Alkyl Groups of Poly(Alkyl methacrylate)s on Inter- and Intramolecular Interactions of Excited Singlet States of Pyrenyl Guest Molecules
  作者：Shibu Abraham、Teresa D. Z. Atvars、Richard G. Weiss

  DOI：10.1021/jp105461r

  日期：2010.9.30

  >400 K, a range that spans the onsets of several relaxation processes in the hosts. Those data indicate that the pyrenyl groups reside near to ester functionalities in most of the PAMAs, although the distance from them (and the main chains) depends upon the bulkiness of the alkyl groups. Among the most important conclusions derived from this research is that the rates of segmental relaxation phenomena

  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。
• Intramolecular, Exciplex-Mediated, Proton-Coupled, Charge-Transfer Processes in <i>N,N</i>-Dimethyl-3-(1-pyrenyl)propan-1-ammonium Cations: Influence of Anion, Solvent Polarity, and Temperature
  作者：Trevor M. Safko、Marcelo M. Faleiros、Teresa D. Z. Atvars、Richard G. Weiss

  DOI：10.1021/acs.jpca.6b01519

  日期：2016.6.16

  proton-coupled, charge-transfer (PCCT) process has been investigated for a series of N,N-dimethyl-3-(1-pyrenyl)propan-1-ammonium cations with different anions (PyS) in solvents of low to intermediate polarity over a wide temperature range. Solvent mediates both the equilibrium between conformations of the cation that place the pyrenyl and ammonium groups in proximity (conformation C) or far from each other

  分子内的激基复合物介导的，质子耦合的电荷转移（PCCT）过程已被研究用于一系列N，N在宽温度范围内的低至中等极性的溶剂中，具有不同阴离子（PyS）的-二甲基-3-（1-苯甲酰基）丙-1-铵阳离子。溶剂介导的阳离子构象之间的平衡（使the烯基和铵基团靠近（构象C）或彼此远离）（构象O）以及铵基团以PyS激发单重态绝热转移质子的能力。 。因此，仅在极性相对较低的氢键接受溶剂（四氢呋喃，乙酸乙酯和1,4-二恶烷）中观察到与PCCT过程同时发生的激基复合物发射，而在二氯甲烷中则未观察到。根据激基复合物发射以及其他光谱和热力学数据，PyS（p K）的激发单重态的构象C处的铵基酸度a *）估计为ca。-3.4在四氢呋喃中。激基复合物的发射强度与局部激发态之间的比率（I Ex / I LE）比激基复合物形成和衰减的速率似乎更依赖于阴离子的性质，尽管激发态数据确实如此。没有提供阴离子对C–O平衡的定量影响