N-ethyl-4-(4-aminobenzylamino)-1,8-naphthalimide | 612836-81-4

• 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: N-ethyl-4-(4-aminobenzylamino)-1,8-naphthalimide
• 英文别名: 6-[(4-Aminophenyl)methylamino]-2-ethylbenzo[de]isoquinoline-1,3-dione；6-[(4-aminophenyl)methylamino]-2-ethylbenzo[de]isoquinoline-1,3-dione
• CAS: 612836-81-4
• 化学式: C₂₁H₁₉N₃O₂
• 分子量: 345.401
• InChiKey: SLHMXLGLYFGOJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-ethyl-4-(4-aminobenzylamino)-1,8-naphthalimide 在 sodium hydroxide 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 disodium N-ethyl-4-{4-[bis(carboxylatomethyl)amino]benzylamino}-1,8-naphthalimide
  参考文献：
  名称：

  Zn（II）的高度选择性和灵敏的荧光PET（光致电子转移）化学传感器。

  摘要：

  将萘二甲酰亚胺衍生物1设计为用于Zn（II）的荧光PET传感器；图1显示了在pH 7.4下对Zn（II）的极好的选择性，即使在存在其他竞争性阳离子的情况下，在识别Zn（II）时也开启了pH独立于pH 3.5以上的发射。

  DOI：

  10.1039/b309569j
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 以 1,4-二氧六环 为溶剂， 生成 N-ethyl-4-(4-aminobenzylamino)-1,8-naphthalimide
  参考文献：
  名称：

  Dual responsive chemosensors for anions: the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule

  摘要：

  The design and synthesis of two novel fluorescent PET anion sensors is described, based on the principle of 'fluorophore-spacer-(anion)receptor'. The sensors 1 and 2 employ simple diaromatic thioureas as anion receptors, and the fluorophore is a naphthalimide moiety that absorbs in the visible part of the spectrum and emits in the green. Upon recognition of anions such as F- and AcO- in DMSO, the fluorescence emission of I and 2 was 'switched off', with no significant changes in the UV-vis spectra. This recognition shows a 1:1 binding between the receptor and the anions. In the case of F-, further additions of the anion, gave rise to large changes in the UV-vis spectra, where the lambda(max) at 455 nm was shifted to 550 nm. These changes are thought to be due to the deprotonation of the 4-amino moiety of the naphthalimide fluorophore. This was in fact found to be the case, using simple naphthalimide derivatives such as 6. Sensors 1 and 2 can thus display dual sensing action; where at low concentrations, the fluorescence emission is quenched, and at higher concentrations the absorption spectra are modulated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01699-x

文献信息

• Highly selective 4-amino-1,8-naphthalimide based fluorescent photoinduced electron transfer (PET) chemosensors for Zn(<scp>ii</scp>) under physiological pH conditions
  作者：Raman Parkesh、T. Clive Lee、Thorfinnur Gunnlaugsson

  DOI：10.1039/b614529a

  日期：——

  The design and synthesis of two novel fluorescent sensors based on the photoinduced electron transfer (PET) concept, and , for the detection of zinc under competitive media is described. These sensors are based on the 4-amino-1,8-naphthalimide fluorophore, which has an absorption band centred at 450 nm and emits in the green with lambda(max) approximately 550 nm. By functionalizing the chromophore

  描述和设计了两种基于光致电子转移（PET）概念的新型荧光传感器，并用于在竞争性介质下检测锌。这些传感器基于4-氨基-1,8-萘二甲酰亚胺荧光团，该团具有以450 nm为中心的吸收带，并以λ（max）大约550 nm的绿色发射。通过在4位上使用简单的基于苄基或乙基-芳基的亚氨基二乙酸酯受体对发色团进行功能​​化，可以实现对Zn（II）的竞争以及其他竞争性过渡以及I和II类金属离子的高选择性和灵敏性。这些传感器还显示出与pH无关，测定的pKa为2.3，这使得它们可以在竞争激烈的pH介质中使用。感测到Zn（II）后，荧光发射光谱为' “开启”表明PET从受体到荧光团的抑制。对于，在1.1 mM EGTA存在下，在pH 7.4缓冲溶液中测量时，Kd = 4 nM可以实现Zn（II）的检测。
• Demonstration of bidirectional photoinduced electron transfer (PET) sensing in 4-amino-1,8-naphthalimide based thiourea anion sensors
  作者：Emma B. Veale、Gillian M. Tocci、Frederick M. Pfeffer、Paul E. Kruger、Thorfinnur Gunnlaugsson

  DOI：10.1039/b907037k

  日期：——

  as fluorescent anion sensors and their photophysical properties investigated upon recognition of biologically relevant anions such as acetate, dihydrogen phosphate and fluoride in DMSO. Synthesised in a single step from their respective aniline precursors, 6–9, these molecules were designed on the fluorophore–spacer–receptor principle, where in the case of sensors 1–3 the thiourea anion recognition moieties

  这 硫脲基于4-氨基-1,8-萘二甲酰亚胺的分子1–5被设计为荧光阴离子传感器，并在识别与生物有关的阴离子（例如乙酸根，磷酸二氢根和氟离子）后对其光物理性质进行了研究。二甲基亚砜。从各自的步骤中一步一步合成苯胺前体6–9，这些分子是根据荧光团-间隔基-受体原理设计的，在传感器1-3的情况下，硫脲阴离子识别部分通过4-氨基部分与荧光团相连，而传感器4和5具有通过CH 2间隔基连接到“酰亚胺”的硫脲部分。目前的研究表明，1-5操作为光诱导电子转移（PET）的传感器，如在它们的吸收光谱中没有观察到显著变化，而它们的荧光发射被在识别离子如ACO淬灭-，H2 PO 4 -和F - ，这表明双向PET感测在这样的基于萘二甲酰亚胺阴离子传感器发生。