N-(2-aminoethyl)-4-(pyren-1-yl)butanamide | 959850-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-(2-aminoethyl)-4-(pyren-1-yl)butanamide
• 英文别名: N-(2-aminoethyl)-4-pyren-1-ylbutanamide
• CAS: 959850-65-8
• 化学式: C₂₂H₂₂N₂O
• 分子量: 330.429
• InChiKey: UGYRGJMUENDVSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)-4-(pyren-1-yl)butanamide 、 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到
  参考文献：
  名称：

  Efficient Construction of Oligocholate Foldamers via “Click” Chemistry and Their Tolerance of Structural Heterogeneity

  摘要：

  The 1,3-dipolar cycloaddition between an alkynyl-terminated cholate trimer and an azido-functionalized cholate hexamer readily afforded the nonamer and dodecamer derivatives; whereas amide coupling employed in previous oligocholate synthesis failed beyond the octamer. Unlike typical oligocholate foldamers with exclusively head-to-tall arrangement of the repeat units, the newly synthesized "clicked" oligocholates contained head-to-head arrangement and flexible tethers in the sequence. Despite large structural perturbations, the clicked oligocholates folded similarly as the parent foldamers, demonstrating the robustness of the solvophobically driven folding mechanism.

  DOI：

  10.1021/ol802364c
• 作为产物：
  描述：

  tert-butyl (2-{[4-(pyren-1-yl)butanoyl]amino}ethyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到N-(2-aminoethyl)-4-(pyren-1-yl)butanamide
  参考文献：
  名称：

  通过铵离子-冠醚相互作用的自组装单壁碳纳米管：锌-卟啉杂化物：结构和电子转移。

  摘要：

  铵离子-冠醚相互作用已成功用于构建卟啉-单壁碳纳米管（SWNT）供体-受体杂化体。[18] crown-6与烷基铵离子的结合策略产生了稳定且可溶于DMF的卟啉-SWNT纳米杂化物。卟啉-SWNT杂化物通过光谱，TEM和电化学技术进行了表征。稳态和时间分辨发射研究均表明卟啉的单线激发态有效猝灭，自由能计算表明发生了电子转移猝灭。纳秒瞬态吸收光谱结果支持电荷分离猝灭过程。还观察到纳米杂化物的电荷稳定化，其中自由基离子对的寿命约为100 ns。在电子池实验中，本纳米杂化物还用于减少己基紫罗兰酸的指示（HV2 +）并氧化溶液中的1-苄基-1,4-二氢烟碱酰胺。以高收率观察到自由基阳离子（HV。+）的积累，这为光诱导电荷分离的发生提供了进一步的证据。本研究表明，氢键基序是一种成功的自组装方法，可用于构建带有供体-受体纳米杂化体的单壁碳纳米管，可用于光能收集和光伏应用。

  DOI：

  10.1002/chem.200700583

文献信息

• Interface molecular engineering of single-walled carbon nanotube/epoxy composites
  作者：Yehai Yan、Jian Cui、Shuai Zhao、Jinfang Zhang、Jiwen Liu、Junmei Cheng

  DOI：10.1039/c1jm14310g

  日期：——

  Dispersion of large single-walled carbon nanotube (SWCNT) bundles into individual nanotubes or small bundles and thus strengthening of the nanotube/matrix interfacial interaction are prerequisites for taking full advantage of the remarkable multifunctional properties of SWCNTs in various carbon nanotube-based composites. Noncovalent functionalization of SWCNTs is an attractive option to simultaneously achieve these conditions. Toward this end, three reactive amino-containing pyrene derivatives (AmPys) with various spacer chain lengths were synthesized. One with the longest spacer length (12 methylene units, AmPy-12) shows the highest functionalization efficiency for SWCNTs in terms of dispersibility. Systematic characterization on a SWCNT/AmPy-12 hybrid suggests that ca. 10 wt% of AmPy-12 is strongly adsorbed on SWCNTs through π–π interactions, making them steadily dispersed into individual ones and/or small bundles without noticeable change in their electronic structure. AmPy-12-functionalized SWCNTs were then used for the preparation of epoxy composites. Since the SWCNT/epoxy interface was well engineered at a molecular level by application of AmPy-12, which interacts noncovalently with SWCNT but bonds chemically to the epoxy matrix, the composite with only 0.3 wt% SWCNTs displays an increase of 54% and 27% in tensile strength and Young's modulus, respectively, over neat resin. A low electrical percolation threshold of 0.1 wt% SWCNTs and improved thermal properties were also observed.

  将大尺寸单壁碳纳米管（SWCNT）束分散成单个纳米管或小束，从而增强纳米管/基体界面相互作用，是充分发挥SWCNT在各种碳纳米管基复合材料中显著多功能特性的前提。对SWCNT进行非共价功能化是同时实现这些条件的一个有吸引力的选择。为此，合成了三种具有不同间隔链长度的含氨基的芘衍生物（AmPys）。其中，间隔长度最长的（12个亚甲基单位，AmPy-12）在分散性方面对SWCNT的功能化效率最高。对SWCNT/AmPy-12混合物的系统表征表明，大约10 wt%的AmPy-12通过π–π相互作用强烈吸附在SWCNT上，使它们稳定地分散成单个纳米管和/或小束，且未明显改变其电子结构。随后，利用功能化的AmPy-12制备了环氧树脂复合材料。由于SWCNT/环氧树脂界面在分子水平上通过应用AmPy-12得到了良好的工程化，AmPy-12与SWCNT之间是非共价相互作用，但与环氧基体则是化学键合，因此仅0.3 wt%的SWCNT复合材料在拉伸强度和杨氏模量上分别比纯树脂提高了54%和27%。同时还观察到0.1 wt%细度的电导阈值和改善的热性能。
• Pyrene‐Functionalised Copper Complexes as Potential Dual‐Modality Imaging Agents
  作者：Jason P. Holland、Victoria Fisher、Jennie A. Hickin、Josephine M. Peach

  DOI：10.1002/ejic.200900823

  日期：2010.1

  -copper complexes are reported. In contrast to previously reported bis(thiosemicarbazonato)Cu 2+ complexes which are nonfluorescent, the pyrene group remains highly fluorescent. The compounds have been characterised by using a wide range of techniques including reverse-phase HPLC, cyclic voltammetry, NMR, electronic absorption (UV/ Vis), infrared and fluorescence emission spectroscopy. Spectroelectrochemistry

  报道了芘官能化的双（缩氨基硫代）锌和 - 铜配合物的合成。与之前报道的非荧光双（缩氨基硫代）Cu 2+ 配合物相比，芘基团仍然具有很强的荧光性。这些化合物已通过使用多种技术进行表征，包括反相 HPLC、循环伏安法、核磁共振、电子吸收 (UV/Vis)、红外和荧光发射光谱。光谱电化学实验表明，Cu 2+ 配合物在生物可接近的电位下经历准可逆的单电子还原。密度泛函理论计算用于探测芘官能化铜配合物的电子结构，并证实基于配体的荧光发射发生是由于芘和双（缩氨基硫代）铜基团之间不存在轨道相互作用。这些初步研究表明，新的铜配合物有可能用作体外细胞荧光显微镜和体内正电子发射断层扫描实验的双模态试剂。
• Self-Assembled Single-Walled Carbon Nanotube:Zinc–Porphyrin Hybrids through Ammonium Ion–Crown Ether Interaction: Construction and Electron Transfer
  作者：Francis D'Souza、Raghu Chitta、Atula S. D. Sandanayaka、Navaneetha K. Subbaiyan、Lawrence D'Souza、Yasuyuki Araki、Osamu Ito

  DOI：10.1002/chem.200700583

  日期：2007.10.5

  An ammonium ion-crown ether interaction has been successfully used to construct porphyrin-single-walled carbon nanotube (SWNT) donor-acceptor hybrids. The [18]crown-6 to alkyl ammonium ion binding strategy resulted in porphyrin-SWNT nanohybrids that are stable and soluble in DMF. The porphyrin-SWNT hybrids were characterized by spectroscopic, TEM, and electrochemical techniques. Both steady-state and

  铵离子-冠醚相互作用已成功用于构建卟啉-单壁碳纳米管（SWNT）供体-受体杂化体。[18] crown-6与烷基铵离子的结合策略产生了稳定且可溶于DMF的卟啉-SWNT纳米杂化物。卟啉-SWNT杂化物通过光谱，TEM和电化学技术进行了表征。稳态和时间分辨发射研究均表明卟啉的单线激发态有效猝灭，自由能计算表明发生了电子转移猝灭。纳秒瞬态吸收光谱结果支持电荷分离猝灭过程。还观察到纳米杂化物的电荷稳定化，其中自由基离子对的寿命约为100 ns。在电子池实验中，本纳米杂化物还用于减少己基紫罗兰酸的指示（HV2 +）并氧化溶液中的1-苄基-1,4-二氢烟碱酰胺。以高收率观察到自由基阳离子（HV。+）的积累，这为光诱导电荷分离的发生提供了进一步的证据。本研究表明，氢键基序是一种成功的自组装方法，可用于构建带有供体-受体纳米杂化体的单壁碳纳米管，可用于光能收集和光伏应用。
• Efficient Construction of Oligocholate Foldamers via “Click” Chemistry and Their Tolerance of Structural Heterogeneity
  作者：Xingang Pan、Yan Zhao

  DOI：10.1021/ol802364c

  日期：2009.1.1

  The 1,3-dipolar cycloaddition between an alkynyl-terminated cholate trimer and an azido-functionalized cholate hexamer readily afforded the nonamer and dodecamer derivatives; whereas amide coupling employed in previous oligocholate synthesis failed beyond the octamer. Unlike typical oligocholate foldamers with exclusively head-to-tall arrangement of the repeat units, the newly synthesized "clicked" oligocholates contained head-to-head arrangement and flexible tethers in the sequence. Despite large structural perturbations, the clicked oligocholates folded similarly as the parent foldamers, demonstrating the robustness of the solvophobically driven folding mechanism.
• Turn-on fluorescence of ruthenium pyrene complexes in response to bovine serum albumin
  作者：Saša Opačak、Margareta Pernar Kovač、Anamaria Brozovic、Ivo Piantanida、Srećko I. Kirin

  DOI：10.1039/d3dt02289g

  日期：——

  Two novel pyrene triphenylphosphine ruthenium conjugates act as fluorescent turn-on beacons for serum albumin, being non-fluorescent in aqueous media but exhibiting strong emission upon binding to BSA. The selective cytotoxicity of the compounds against tumour cells is enhanced upon irradiation by UV-light, paving the way for application in photodynamic therapy under two-photon excitation.

  两种新型芘三苯基膦钌缀合物充当血清白蛋白的荧光开启信标，在水介质中不发出荧光，但在与 BSA 结合后表现出强发射。该化合物对肿瘤细胞的选择性细胞毒性在紫外光照射下增强，为双光子激发下的光动力疗法的应用铺平了道路。