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。
• Dual responsive chemosensors for anions: the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule
  作者：Thorfinnur Gunnlaugsson、Paul E. Kruger、T.Clive Lee、Raman Parkesh、Frederick M. Pfeffer、Gillian M. Hussey

  DOI：10.1016/s0040-4039(03)01699-x

  日期：2003.8

  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.
• A highly selective and sensitive fluorescent PET (photoinduced electron transfer) chemosensor for Zn(ii)Electronic supplementary information (ESI) available: synthesis, experimental details and 1H and 13C NMR for 1, 2 and 3. UV-Vis Zn(ii) titrations, fluorescence titration for pH, Hg2+ and Cd2+ for 1. See http://www.rsc.org/suppdata/ob/b3/b309569j/
  作者：Thorfinnur Gunnlaugsson、T. Clive Lee、Raman Parkesh

  DOI：10.1039/b309569j

  日期：——

  The naphthalimide derivative 1 was designed as a fluorescence PET sensor for Zn(II); 1 showed excellent selectivity for Zn(II) at pH 7.4, even in the presence of other competitive cations, the emission, being pH independent above pH 3.5, was switched on upon Zn(II) recognition.

  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。