6-(9-fluorenyl)-1,4,8,11-tetraazaundecane-5,7-dione | 253799-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 6-(9-fluorenyl)-1,4,8,11-tetraazaundecane-5,7-dione
• 英文别名: Bis(2-aminoethyl)-2-(9-fluorenyl)malonamide；N,N'-bis(2-aminoethyl)-2-(9H-fluoren-9-yl)propanediamide
• CAS: 253799-42-7
• 化学式: C₂₀H₂₄N₄O₂
• 分子量: 352.436
• InChiKey: CNMLTDFIBQIOOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 6-(9-fluorenyl)-1,4,8,11-tetraazaundecane-5,7-dione 在 NaOH 作用下， 以 水 为溶剂， 以52%的产率得到[Cu(6-(9-fluorenyl)-1,4,8,11-tetraazaundecane-5,7-dione)-2H]*2H2O*0.25(ethylenediamine)
  参考文献：
  名称：

  A new dioxotetraamine ligand appended with fluorenyl and its copper(II) complex. Synthesis, crystal structure and solution behavior

  摘要：

  A new dioxotetraamine ligand 6-(9-fluorenyl)-1,4,8,11-tetraazaundecane-5,7-dione (L) and its copper(II) complex have been synthesized. Detailed studies have been made on solution chemistry of Cu(II), Ni(II) and Co(II) complexes of the ligand by pH-potentiometric and fluorimetric titration as well as cyclic voltammetry. The coordination of Cu2+ and Ni(2+)quenches the fluorescence of fluorenyl in the ligand through an electron transfer mechanism. The crystal structure of [Cu(H-2L)] was determined. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(99)00305-9
• 作为产物：
  描述：

  diethyl 2-(9-fluorenyl)malonate 、 乙二胺 反应 72.0h， 生成 6-(9-fluorenyl)-1,4,8,11-tetraazaundecane-5,7-dione
  参考文献：
  名称：

  Turn-off Fluorescence Chemosensor for Iron with Bis(2-aminoethyl)-2-(9-fluorenyl)malonamide Functionlized SBA-15

  摘要：

  一种双(2-氨基乙基)-2-(9-芴基)马隆酰胺作为荧光探针配体，通过后合成接枝法固定到介孔硅材料SBA-15上。所获得的材料通过小角和宽角X射线衍射、氮气吸附-脱附、傅里叶变换红外光谱、拉曼光谱和热重分析进行表征，结果表明配体成功固定在介孔硅的表面。通过将Fe³⁺、Mg²⁺、Cr³⁺、Co²⁺、Ni²⁺、Cu²⁺、Hg²⁺和Zn²⁺等阳离子添加到被检测固体的水悬浊液中，研究了所获得材料的传感能力。在所有测试的阳离子中，向该材料悬浊液中添加Fe³⁺离子导致荧光强度下降最大。与其他阳离子相比，该材料对铁离子的关闭光致光发光表现出显著的效果。该材料的荧光强度与Fe³⁺离子的浓度之间建立了良好的线性关系，使其成为检测Fe³⁺离子的荧光化学传感器，具有适合的检测限为1.35 × 10⁻⁵。它可以作为一种新型荧光传感器在水溶液中应用于许多实际的化学、环境和生物系统中。

  DOI：

  10.1007/s10895-013-1321-8

文献信息

• Synthesis and Solution Behavior Studies of a Bifunctional Fluorenyl Dioxotetraamine and Its Copper(II) Complex
  作者：Yi-Ning Wang、Qin-Hui Luo

  DOI：10.1002/zaac.201700221

  日期：2017.11.2

  The fluorenyl dioxotetraamine L4 was designed and prepared. The solution behavior of L4 and its interaction with the CuII ion were studied by pH potentiometric, fluorimetric and spectrophotometric titration. In the dioxane/water solution, it was found that the molecule L4 showed an “off-on” or “on-off” fluorescent response in the absence or presence of the CuII ion with the increase of the pH value

  设计并制备了芴基二氧代四胺L4。L4 的溶液行为及其与 CuII 离子的相互作用通过 pH 电位、荧光和分光光度法滴定进行研究。在二恶烷/水溶液中，发现分子L4在CuII离子不存在或存在的情况下，随着pH值的增加，呈现“关-开”或“开-关”的荧光响应。此外，受 CuII 离子的影响，当 pH 值略高于 4.0 时，二氧四胺 L4 的荧光几乎可以淬灭，这很少被报道，可用于在酸性条件下检测 CuII 离子。
• Fluorenyl-Schiff-base ligands and their dicopper(II) complexes. Synthesis, structural and spectroscopic characterization and DNA binding assays
  作者：Fabiane dos Santos Carlos、Marcelo Carpes Nunes、Bernardo Almeida Iglesias、Priscilla J. Zambiazi、Manfredo Hörner、Guilherme A. de Moraes、Guilherme Sippel Machado、Ronny Rocha Ribeiro、Fábio Souza Nunes

  DOI：10.1016/j.poly.2018.01.003

  日期：2018.4

  complexes [Cu2(L1)2]·2H2O and [Cu2(L2)](ClO4)4·4H2O, respectively, and to their corresponding spin orbit coupling constants λ = −428 and −398 cm−1. The EPR spectrum of [Cu2(L2)](ClO4)4·4H2O in the solid state showed a half-field ΔmS = ±2 transition, supporting the dicopper composition. The fluorenyl copper(II) derivatives demonstrated a moderate binding to ct-DNA than the fluorenyl-ligand molecule following

  摘要以水杨醛和2,6-二甲酰基4-甲基苯酚与6-（9-芴基）-1,4,8,11-四氮杂十二烷-5,7-为缩合剂，合成了含芴为荧光团的席夫碱配体L1和L2。 dione。通过元素分析，ESI-MS，1H和13C NMR，FTIR，EPR，UV-Vis和发射光谱学进行了全面的光谱分析。配体L1与铜（II）结合形成[Cu2（L1）2]·2H2O，该晶体在正交晶系和空间群P21 / n中结晶。通过对UV-Vis和EPR光谱的分配，可以得到络合物[Cu2（L1）2]·2H2O和[Cu2（L2）]（ClO4）4·在6345和5435 cm-1处的Jahn-Teller稳定能（EJT）。分别为4H2O和与其对应的自旋轨道耦合常数λ= -428和-398 cm-1。固态[Cu2（L2）]（ClO4）4·4H2O的EPR光谱显示半场ΔmS=±2跃迁，支持双铜组成。芴基铜（II）衍生物表现出比芴基配体分子更适
• New fluorenyl-substituted ditopic dioxotetraamine ligands and their copper(ii) complexes—synthesis, crystal structure, magnetic properties and solution behavior
  作者：Qing-Xiang Li、Yi-Ning Wang、Qin-Hui Luo、Xue-Lei Hu、Yi-Zhi Li

  DOI：10.1039/b717866b

  日期：——

  A new fluorenyl-substituted dioxotetraamine salicylaldehyde Schiff-base ligand (L1) has been synthesized by the non-template 1 + 2 condensation of ligand 6-(9-fluorenyl)-1,4,8,11-tetraazaundecane-5,7-dione (L) with salicylaldehyde. From reduction of L1 with an excess of NaBH4, a ditopic dioxotetraamine ligand (L2) has been obtained. The copper(II) complex of L1 has been synthesized and its properties

  一种新的芴基取代的二氧四胺水杨醛席夫碱 配体（L 1）是通过非模板1 + 2缩合合成的配体 6-（9-芴基）-1,4,8,11-四氮杂十一烷-5,7-二酮 （L）与 水杨醛。从减少L 1与过量的NaBH 4（一种双位二氧四胺）配体已获得（L 2）。合成了L 1的铜（II）配合物。质谱仪确定了变温磁化率及其晶体结构。通过pH电位法和荧光法对L 2的Cu（II）配合物的溶液化学进行了详细的研究。滴定法。
• A novel fluorene-derivative Schiff-base fluorescent sensor for copper(II) in organic media
  作者：Fabiane dos Santos Carlos、Marcelo Carpes Nunes、Leonardo De Boni、Guilherme Sippel Machado、Fábio Souza Nunes

  DOI：10.1016/j.jphotochem.2017.08.022

  日期：2017.11

  solutions. Fluorescence was quenched upon coordination, showing selectivity for Cu(II) over Mn(II), Fe(III), Ni(II), Pd(II), Zn(II), Ca(II), Hg(II), Na(I) and K(I) in a concentration range of 1.00 to 10.0 × 10‐7 mol L‐1. Good results were observed for sensor 1 derived from 2‐formylpiridine. Benesi‐Hilderbrand formalism indicates that the most abundant species formed have 2:1 (metal/ligand) ratio with

  合成了一种新的含芴的席夫碱传感器，并进行了研究，以测定二甲基亚砜溶液中的金属离子。配位猝灭后，荧光猝灭，显示出对Cu（II）的选择性高于Mn（II），Fe（III），Ni（II），Pd（II），Zn（II），Ca（II），Hg（II），Na （I）和K（I）的浓度范围为1.00至10.0×10 -7  mol L -1。衍生自2-甲酰基吡啶的传感器1观察到良好的结果。Benesi-Hilderbrand形式主义表明，形成的最丰富的物种的比例为2：1（金属/配体），计算的出价常数为1.74×10 12 L 2  mol -2，与Stern-Volmer常数K SV为2.26× 10 12 升2 摩尔-2。Cu（II）的检出限（LOD）为0.037μmolL -1，在3.00至7.00×10 -7  mol L的铜（II）浓度范围内，相对标准偏差（RSD）为3.19％。‐1。
• Turn-off Fluorescence Chemosensor for Iron with Bis(2-aminoethyl)-2-(9-fluorenyl)malonamide Functionlized SBA-15
  作者：Marzieh Yadavi、Alireza Badiei

  DOI：10.1007/s10895-013-1321-8

  日期：2014.3

  An bis(2-aminoethyl)-2-(9-fluorenyl)malonamide as fluorophore ligand was immobilized onto mesoporous silica type SBA-15 via post synthesis grafting. The obtained material was characterized by small and wide angle X-ray diffraction, N2 adsorption–desorption, Fourier transform infrared spectroscopy, Raman spectroscopy and thermogravimetric analysis that indicate the successful immobilization of the ligand on the surface of mesoporous silica. The sensing ability of the obtained material was studied by addition of the cations Fe3+, Mg2+, Cr3+, Co2+, Ni2+, Cu2+, Hg2+ and Zn2+ to water suspensions of the assayed solid. Of all the cations tested addition of Fe3+ ion to a suspension of this material resulted in the largest decrease in the fluorescence intensity. Turn-off photoluminescence of this material was remarkably observed for iron ions in comparing of the other cations. A good linearity between the fluorescence intensity of this material and the concentration of Fe3+ ion is constructed, which enables it as a fluorescence chemosensor for detecting the Fe3+ ion with a suitable detection limit of 1.35 × 10−5. It can be introduced as a novel fluorescent sensor in aqueous solution for a lot of practical applications in chemical, environmental and biological systems.

  一种双(2-氨基乙基)-2-(9-芴基)马隆酰胺作为荧光探针配体，通过后合成接枝法固定到介孔硅材料SBA-15上。所获得的材料通过小角和宽角X射线衍射、氮气吸附-脱附、傅里叶变换红外光谱、拉曼光谱和热重分析进行表征，结果表明配体成功固定在介孔硅的表面。通过将Fe³⁺、Mg²⁺、Cr³⁺、Co²⁺、Ni²⁺、Cu²⁺、Hg²⁺和Zn²⁺等阳离子添加到被检测固体的水悬浊液中，研究了所获得材料的传感能力。在所有测试的阳离子中，向该材料悬浊液中添加Fe³⁺离子导致荧光强度下降最大。与其他阳离子相比，该材料对铁离子的关闭光致光发光表现出显著的效果。该材料的荧光强度与Fe³⁺离子的浓度之间建立了良好的线性关系，使其成为检测Fe³⁺离子的荧光化学传感器，具有适合的检测限为1.35 × 10⁻⁵。它可以作为一种新型荧光传感器在水溶液中应用于许多实际的化学、环境和生物系统中。