N-[(chloromethyl)carbonyl]-1-pyrenemethylamine | 281660-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N-[(chloromethyl)carbonyl]-1-pyrenemethylamine
• 英文别名: 2-chloro-N-(pyren-1-ylmethyl)acetamide；N-(1-pyrenylmethyl)-2-chloroacetamide；N-(1-pyrenylmethyl)chloroacetamide；N-(1-pyrenemethyl)chloroacetamide；2-Chloro-N-[(pyren-1-YL)methyl]acetamide
• CAS: 281660-03-5
• 化学式: C₁₉H₁₄ClNO
• 分子量: 307.779
• InChiKey: QQOUZKRZNRMMSR-UHFFFAOYSA-N

物化性质

• 沸点：
  580.4±43.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 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：

  N-[(chloromethyl)carbonyl]-1-pyrenemethylamine 在 二异丙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 1,4,7,10-tetraazacyclododecane-10-(N-(1-pyrenylmethyl)-acetamide)-1,4,7-triacetic acid
  参考文献：
  名称：

  Pyrene-sensitised near-IR luminescence from ytterbium and neodymium complexes

  摘要：

  研究表明，镱和钕在激发芘发色团后会产生敏化发射。在自组装复合物和带有下垂芘基团的偶氮杂环衍生物中也显示了敏化发射。这些系统中的能量转移取决于配体和络合物之间联系的性质。

  DOI：

  10.1039/b401302f
• 作为产物：
  描述：

  芘-1-基甲胺 、 氯乙酰氯 在 potassium carbonate 作用下， 生成 N-[(chloromethyl)carbonyl]-1-pyrenemethylamine
  参考文献：
  名称：

  Metal ion induced FRET On–Off in naphthyl-pyrenyl pendent tetrahomodioxacalix[4]arene

  摘要：

  A novel tetrahomodioxacalix[4]arene (7) bearing both naphthyl- and pyrenyl-amide pendants was synthesized as FRET-based fluorometric sensor for Cu2+ ion. Intramolecular FRET from the naphthalene emission to the pyrene absorption affords Cu2+ ion selectivity over other metal ions. Upon addition of Cu2+ ion, the complex solution of 7 gave a significantly decreased pyrene acceptor emission along with an enhancement of naphthalene donor emission via FRET On-Off event. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.083

文献信息

• Ratiometric fluorescent chemosensor for selective detection of Hg (II) ions
  申请人：Chang Suk-Kyu

  公开号：US20080255346A1

  公开（公告）日：2008-10-16

  A mercury selective fluorescent chemosensor for detecting mercury ions (Hg 2+ ) by a compound represented by formula 1 is provided. A novel fluorescent sensitive compound prepared by introducing two aminopyrene functions as a fluorescent sensitive moiety into a binding site of the compound represented by the formula 1, is used for selectively detecting mercury ions (Hg 2+ ) is also provided. The mercury selective fluorescent sensitive chemosensor is a switch type chemosensor having ON-OFF-type Hg 2+ -selective fluorescence quenching behavior and is not affected by other coexistent metal ions. The changes in fluorescence of the compounds represented by formula 1 were analyzed by ratiometric approach using monomer and excimer emissions of the pyrene fluorophore to selectively signal the concentration of mercury ions (Hg 2+ ). The chemosensor can detect mercury ions in a micromolar unit even in a solution including an excess of water. Accordingly, the mercury selective fluorescent chemosensor for detecting mercury ions (Hg 2+ ) can be used effectively in environmental and medical applications.

  提供一种用于检测汞离子（Hg2+）的汞选择性荧光化学传感器，该传感器由代表式1的化合物提供。还提供了一种新型荧光敏感化合物，通过将两个氨基芘功能引入代表式1的化合物的结合位点作为荧光敏感基团，用于选择性检测汞离子（Hg2+）。该汞选择性荧光敏感化学传感器是一种开关型传感器，具有ON-OFF型Hg2+选择性荧光猝灭行为，并不受其他共存金属离子的影响。通过使用芘荧光团的单体和激聚物发射的比率法分析代表式1的化合物的荧光变化，以选择性地信号汞离子（Hg2+）的浓度。该化学传感器可以在包含过量水的溶液中以微摩尔单位检测汞离子。因此，用于检测汞离子（Hg2+）的汞选择性荧光化学传感器可以有效应用于环境和医学领域。
• Varied nanostructures from a single multifunctional molecular material
  作者：David Canevet、Ángel Pérez del Pino、David B. Amabilino、Marc Sallé

  DOI：10.1039/c0jm02302g

  日期：——

  The control of the morphology of nanostructures formed from a single component molecular material incorporating electron accepting and donating moieties is shown, from both solution and gel states. The compound comprises one tetrathiafulvalene (TTF) and two pyrene units which act as the π-electron rich and deficient units, respectively, and which are united by amide-containing linkers whose additional role is to aide aggregation by hydrogen bonding. This role was demonstrated by IR and NMR spectroscopy. The gels were deposited onto surfaces and the solvent allowed to evaporate, leaving films formed by meshes of fibres with different morphologies in accord with the different solvents used to form the materials. Doping of these xerogels with iodine vapour afforded conducting films whose characteristics were probed with current sensing atomic force microscopy (CS-AFM), providing current maps and I–V curves which show how dramatically the processing solvent can influence the electronic properties of these xerogel-derived materials.

  展示了来自单一组分分子材料的纳米结构形态的控制，这些材料包含电子受体和供体部分，适用于溶液和凝胶状态。该化合物由一个四硫杂富瓦烯（TTF）和两个芘单元组成，分别充当π-电子丰富和匮乏的单元，并通过含酰胺的链接剂结合在一起，这些链接剂的额外作用是通过氢键促进聚集。通过红外光谱（IR）和核磁共振（NMR）光谱证明了这一作用。这些凝胶被沉积在表面上，溶剂允许蒸发，留下由不同形态纤维网形成的薄膜，具体取决于用于制备材料的不同溶剂。用碘蒸气掺杂这些干凝胶产生的导电薄膜的特性通过电流传感原子力显微镜（CS-AFM）进行了探测，提供了电流图和I–V曲线，显示加工溶剂可以显著影响这些干凝胶衍生材料的电子特性。
• An excimer emission approach for patterned fluorescent imaging
  作者：Jong-Man Kim、Sung Jun Min、Soon W. Lee、Ju Han Bok、Jong Seung Kim

  DOI：10.1039/b501568e

  日期：——

  Selective removal of t-Boc protecting groups in a polymer film imbedded, pyrene-containing calixarene derivative results in the generation of a patterned fluorescence image without employing wet developing processes.

  选择性去除聚合物薄膜中的 t-Boc 保护基团和含芘的咔唑烯衍生物，无需采用湿法显影工艺即可生成图案化荧光图像。
• Pyrene-appended calix[4]crowned logic gates involving normal and reverse PET: NOR, XNOR and INHIBIT
  作者：Seoung Ho Lee、Jong Yeol Kim、Sung Kuk Kim、Joung Hae Lee、Jong Seung Kim

  DOI：10.1016/j.tet.2004.04.061

  日期：2004.6

  As a novel sensing system, N-(1-pyrenylmethyl) amide-appended calix[4]crown-5 (2) and crown-6 (3) have been newly synthesized. Judging from the fluorescence changes upon the addition of cations, 3 having crown-6 ring showed the Pb2+ ion selectivity over other cations tested regarding fluorescence quenching. Upon the Pb2+ ion coordination to two amide oxygen atoms with aid of crown ring, a reverse-photo-induced

  作为新颖的感测系统，新合成了N-（1-苯甲基甲基）酰胺附加的杯[4] crown-5（2）和crown-6（3）。从在添加阳离子的荧光变化来看，3具有冠-6环显示出的Pb 2+离子选择性相对于其它阳离子测试关于荧光淬灭。在Pb 2+离子借助冠环与两个酰胺氧原子配位后，发生反向光诱导电子转移（PET），以使电子从the基转移至电子缺电子的酰胺氧原子，从而得到淬灭的荧光。通过在溶液中加入HClO 4或三乙胺如图3所示，由于从pyr基到质子化的酰胺氧原子的反向PET和从三乙胺形成的氮阴离子到pyr基的正常PET，荧光强度降低。对于3，仅当不添加三乙胺和Pb（ClO 4）2（输入A和B）（A = B：0）时，才操作在395 nm处出现强荧光信号的NOR逻辑门。。仅当同时添加两个输入（三乙胺和HClO 4，A = B：1）或两个输入都不添加（A = B：0）时，XNOR门也才操作。然后，对于3，还使用HClO
• Pyrene Excimer-Based Calix[4]arene FRET Chemosensor for Mercury(II)
  作者：Young Hoon Lee、Min Hee Lee、Jun Feng Zhang、Jong Seung Kim

  DOI：10.1021/jo101113f

  日期：2010.11.5

  A novel calix[4]arene derivative locked in the 1,3-alternate conformation (2) bearing two pyrene and rhodamine fluorophores was synthesized as a selective sensor for the Hg2+ ion. The sensoring is based on FRET from pyrene excimer emissions to ring-opened rhodamine absorption upon complexation of the Hg2+ ion. Addition of Hg2+ to a mixed solution of 2 gave significantly enhanced fluorescence at ∼576

  合成了一种新颖的杯[4]芳烃衍生物，该衍生物锁定在带有两个pyr和若丹明荧光团的1,3-交替构象（2）中，作为Hg 2+离子的选择性传感器。传感基于从RET准分子的发射到Hg 2+离子络合后开环若丹明吸收的FRET 。通过FRET在343 nm激发下，将Hg 2+添加到2的混合溶液中可在〜576 nm处显着增强荧光。我们还发现，由分子内π-π相互作用形成的pyr准分子发射比获得分子间π-π相互作用所产生的RET分子更有效。