N-(4-aminobutyl)pyrene-1-sulfonamide | 886843-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-(4-aminobutyl)pyrene-1-sulfonamide
• 英文别名: N-pyrenesulfonylbutanediamine；N-(4-Aminobutyl)pyrene-1-sulfonamide
• CAS: 886843-98-7
• 化学式: C₂₀H₂₀N₂O₂S
• 分子量: 352.457
• InChiKey: DCTREJXLEQJDIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-aminobutyl)pyrene-1-sulfonamide 在 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 3-(bis(2-hydroxyethyl)amino)-N-(4-(pyrene-1-sulfonamido)butyl)propanamide
  参考文献：
  名称：

  A novel surfactant-like fluorophore and its probing ability to the aggregation of amphiphilic compounds

  摘要：

  A novel surfactant-like non-ionic fluorophore, 3-(bis(2-hydroxyethyl)amino)-N-(4-(pyrene-1-sulfonamido)butyl) propanamide (PSDA-DEA), was designed and prepared. Fluorescence and surface tension studies revealed that the fluorophore aggregates in aqueous medium, and its critical aggregation concentration (CAC) is similar to 3.3 x 10(-5) M. Cryogenic transmission electron microscopy (cryo-TEM), dynamic light scattering (DLS) and atomic force microscopy (AFM) measurements demonstrated that the diameter of the aggregates as formed is of a few hundred nano-meters. It was also shown that the profile of the emission spectrum of the compound is well dependent upon the polarity of its medium, as indicated by a change up to 53% of its intensity ratio at 399 nm and 380 nm (I-399/I-380) when the solvent changed from water to ethanol. It is of the polarity sensitive property that the fluorophore can be used for monitoring micelle formation of several anionic, cationic and non-ionic surfactants. Furthermore, PSDA-DEA is also a valuable probe for sensing transition of different aggregates such as micelles to vesicles. Comparative studies demonstrated that the present probe is more versatile than pyrene when it is used as a fluorescence probe. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.07.001
• 作为产物：
  描述：

  芘 在 盐酸 、 氯磺酸 、 氯化亚砜 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 N-(4-aminobutyl)pyrene-1-sulfonamide
  参考文献：
  名称：

  液体混合物如何溶解不溶性凝胶剂？四氢呋喃-水混合物中芘-接头-葡糖酸凝胶剂的自组装特性

  摘要：

  一系列含有 α,ω-二氨基烷烃间隔基（Pn，其中 n，分隔氨基的亚甲基单元数，为 2, 3, 4, 6, 7, 8) 在室温下检查 v:v 四氢呋喃 (THF): 水混合物。2 w/v % 浓度的 Pn 在室温下不溶于 THF 或水中。然而，Pn 可以溶解在一些 THF：水混合物中，并且它们在其他组合物中自发形成凝胶而不会完全溶解。已经使用多种技术研究了液体混合物中 Pn 的自组装。Pn 在其溶液/溶胶中的粒径、临界胶凝浓度、微观结构、凝胶的热稳定性和机械稳定性，发现 Pn 分子在其凝胶网络中的分子堆积模式非常依赖于液体混合物的组成。Pn 的自组装行为与液体混合物的极性之间的相关性，如 E(T)(30) 和 Hansen 溶解度参数所探讨的，对 Pn 的自组装为什么可以或不可以产生定性和定量的见解以不同的液体组合物实现。正如紫外-可见光和荧光光谱研究所揭示的那样，芘基的 π-π 堆积是聚集过程的一部分。凝胶的流变特性与

  DOI：

  10.1021/ja402560n

文献信息

• Fluorescent film sensors based on SAMs of pyrene derivatives for detecting nitroaromatics in aqueous solutions
  作者：Shujuan Zhang、Liping Ding、Fengting Lü、Taihong Liu、Yu Fang

  DOI：10.1016/j.saa.2012.04.041

  日期：2012.11

  The detection of nitroaromatics in aqueous solutions by a novel pyrene-functionalized film has been investigated in the present study. The pyrene moieties were attached on the glass surface via a long flexible spacer based on self-assembled monolayer technique. Steady-state fluorescence measurements revealed that these surface-attached pyrene moieties exhibited both monomer and excimer emission. Nitroaromatics such as 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, and 2,4,6-trinitrophenol (picric acid) were found to efficiently quench the fluorescence emission of this film. The quenching results demonstrated that the excimer emission of these surface-confined pyrene moieties is more sensitive to the presence of nitroaromatics than the monomer emission. The quenching mechanism was examined through fluorescence lifetime measurement and it revealed that the quenching is static in nature and may be caused by electron transfer from the polycyclic aromatics to the nitroaromatics. Furthermore, the response of the film to nitroaromatics is fast and reversible, and the obtained film shows promising potentials in detecting explosives in aqueous environment. (C) 2012 Elsevier B.V. All rights reserved.
• How Do Liquid Mixtures Solubilize Insoluble Gelators? Self-Assembly Properties of Pyrenyl-Linker-Glucono Gelators in Tetrahydrofuran–Water Mixtures
  作者：Ni Yan、Zhiyan Xu、Kevin K. Diehn、Srinivasa R. Raghavan、Yu Fang、Richard G. Weiss

  DOI：10.1021/ja402560n

  日期：2013.6.19

  The self-assembly behavior of a series of glucono-appended 1-pyrenesulfonyl derivatives containing α,ω-diaminoalkane spacers (Pn, where n, the number of methylene units separating the amino groups, is 2, 3, 4, 6, 7, and 8) in v:v tetrahydrofuran (THF):water mixtures is examined at room temperature. The Pn at 2 w/v % concentrations do not dissolve in either THF or water at room temperature. However

  一系列含有 α,ω-二氨基烷烃间隔基（Pn，其中 n，分隔氨基的亚甲基单元数，为 2, 3, 4, 6, 7, 8) 在室温下检查 v:v 四氢呋喃 (THF): 水混合物。2 w/v % 浓度的 Pn 在室温下不溶于 THF 或水中。然而，Pn 可以溶解在一些 THF：水混合物中，并且它们在其他组合物中自发形成凝胶而不会完全溶解。已经使用多种技术研究了液体混合物中 Pn 的自组装。Pn 在其溶液/溶胶中的粒径、临界胶凝浓度、微观结构、凝胶的热稳定性和机械稳定性，发现 Pn 分子在其凝胶网络中的分子堆积模式非常依赖于液体混合物的组成。Pn 的自组装行为与液体混合物的极性之间的相关性，如 E(T)(30) 和 Hansen 溶解度参数所探讨的，对 Pn 的自组装为什么可以或不可以产生定性和定量的见解以不同的液体组合物实现。正如紫外-可见光和荧光光谱研究所揭示的那样，芘基的 π-π 堆积是聚集过程的一部分。凝胶的流变特性与
• A novel surfactant-like fluorophore and its probing ability to the aggregation of amphiphilic compounds
  作者：Lei Zhang、Lining Gao、Qiaojun Liu、Feipeng Yang、Yu Fang

  DOI：10.1016/j.jphotochem.2012.07.001

  日期：2012.10

  A novel surfactant-like non-ionic fluorophore, 3-(bis(2-hydroxyethyl)amino)-N-(4-(pyrene-1-sulfonamido)butyl) propanamide (PSDA-DEA), was designed and prepared. Fluorescence and surface tension studies revealed that the fluorophore aggregates in aqueous medium, and its critical aggregation concentration (CAC) is similar to 3.3 x 10(-5) M. Cryogenic transmission electron microscopy (cryo-TEM), dynamic light scattering (DLS) and atomic force microscopy (AFM) measurements demonstrated that the diameter of the aggregates as formed is of a few hundred nano-meters. It was also shown that the profile of the emission spectrum of the compound is well dependent upon the polarity of its medium, as indicated by a change up to 53% of its intensity ratio at 399 nm and 380 nm (I-399/I-380) when the solvent changed from water to ethanol. It is of the polarity sensitive property that the fluorophore can be used for monitoring micelle formation of several anionic, cationic and non-ionic surfactants. Furthermore, PSDA-DEA is also a valuable probe for sensing transition of different aggregates such as micelles to vesicles. Comparative studies demonstrated that the present probe is more versatile than pyrene when it is used as a fluorescence probe. (C) 2012 Elsevier B.V. All rights reserved.