2-(2-aminoethyl)-6-((2-aminoethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 150588-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-aminoethyl)-6-((2-aminoethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-(2-Aminoethyl)-6-(2-aminoethylamino)benzo[de]isoquinoline-1,3-dione
• CAS: 150588-57-1
• 化学式: C₁₆H₁₈N₄O₂
• 分子量: 298.345
• InChiKey: OGUIKULWHUCRNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  561.4±50.0 °C(predicted)
• 密度：
  1.371±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-aminoethyl)-6-((2-aminoethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione 、 氯乙酸甲酯 在 sodium dihydrogenphosphate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  A highly selective 1,8-naphthalimide probe for recognition of casein based on aggregation induced emission enhancement characteristics

  摘要：

  A water-soluble 1,8-naphthalimide-based fluorescent probe 1, bearing four acetic carboxylic groups, exhibited high selectivity and sensitivity for recognition of casein based on the aggregation induced emission enhancement (AIEE) character. The AIEE mechanism of probe 1 with casein was studied by fluorescence and circular dichroism (CD) spectra. Base on the AIEE characteristics of probe 1, a novel fluorometric method for casein quantification in the PBS (pH = 7.4) was developed. The linear range of the calibration curve was 0.1-11.0 mu g mL(-1) with a correlation coefficient of 0.9978. The detection limit was estimated to be 2.0 ng mL(-1). The proposed method has been applied to the determination of casein in milk powder samples and the results were in good agreement with the result of Biuret method. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.12.017
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 、 乙二胺 以 乙醇 为溶剂， 反应 12.0h， 以91%的产率得到2-(2-aminoethyl)-6-((2-aminoethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis and Enhanced Properties of Fluorescence-Based Polyurethane Films by Covalently Bonding 1,8-Naphthalimide

  摘要：

  通过共价键合不同量的2-(2-氨基乙基)-6-((2-氨基乙基)氨基)-1H-苯并[de]异喹啉-1合成了一系列基于荧光的聚氨酯薄膜(AABD-PU)， 3(2H)-二酮(AABD)作为扩链剂进入聚氨酯链，是一种新型氨基功能化的1,8-萘二甲酰亚胺荧光染料。通过1H NMR和FT-IR光谱证实了AABD的化学结构。通过紫外可见光谱（UV-visible）研究了合成的 AABD-PU 中的 AABD 片段含量，并通过荧光光谱表征了 AABD-PU 的增强性能。结果发现，与 AABD 相比，AABD-PU 的紫外可见吸收和荧光发射最大值分别出现蓝移。由于AABD微环境的变化，AABD-PU的荧光强度明显增强。此外，AABD-PU的荧光表现出良好的稳定性，不仅对温度而且对荧光猝灭剂也如此。此外，荧光团永久固定在聚氨酯链中，难以迁移。

  DOI：

  10.14233/ajchem.2014.16233

文献信息

• The design, synthesis and photophysical properties of two novel 1,8-naphthalimide fluorescent pH sensors based on PET and ICT
  作者：Nikolai I. Georgiev、Vladimir B. Bojinov、Peter S. Nikolov

  DOI：10.1016/j.dyepig.2010.08.004

  日期：2011.3

  The changes in the photophysical properties of two novel yellow green emitting pH chemosensors namely a 1 8-naphthalimide dye and its condensed heterocyclic derivative as a function of pH were investigated in water/ethanol The 1 8-naphthalimide dye displayed on-off pH sensing properties owing to photoinduced electron transfer while its condensed heterocyclic derivative revealed off-on-off pH sensor activity derived from simultaneous photoinduced electron transfer and internal charge transfer In alkaline media the fluorescence of the 1 8-naphthailimide dye was quenched owing to photoinduced electron transfer being disabled in acidic media The pK(a) of the 1 8-naphthailimide dye was 549 which defines the dye as a highly efficient off on switch For the heterocyclic 1 8-naphthalimide derivative two fluorescence quenching processes at different pH were observed one with a pK(a) value of 608 and a second with a pK(a) value of 395 These results indicate that the heterocyclic derivative would be able to act as an efficient off on off fluorescent pH switch (C) 2010 Elsevier Ltd All rights reserved
• Fluorescent and thermal properties of siloxane-polyurethanes based on 1,8-naphthalimide
  作者：Yan Ma、Qian-Yun Tang、Ji Zhu、Li-Hong Wang、Cheng Yao

  DOI：10.1016/j.cclet.2014.01.048

  日期：2014.5

  A series of fluorescent siloxane-polyurethanes (HPMS-PUs) containing an amino-functionalized, 1,8-naphthalimide, fluorescent monomer (AABD) as a chain extender were synthesized. The properties of the HPMS-PUs were investigated by UV-vis and fluorescence spectroscopies, thermogravimetric analysis and thermal migration behavior. The maximum absorption and emission wavelengths of HPMS-PUs showed a red shift of about 4 nm and a blue shift of about 9 nm, respectively, compared to those of AABD. The Stokes shifts of AABD and HPMS-PU2 were 3514 and 2931 cm(-1), respectively. The quantum yield of HPMS-PU2 was 0.79, which was six times higher than that of AABD. Concentration self-quenching was observed in both AABD and HPMS-PUs. The fluorescence of HPMS-PUs was quite stable with respect to both temperature and fluorescence quencher effects. The thermal stability of HPMS-PUs increased with AABD content. The fluorophore units in the HPMS-PUs did not readily migrate. (C) 2014 Cheng Yao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.