2-(4-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)phenyl)-6-amino-1H-benzo[d,e]isoquinoline-1,3(2H)-dione | 1286630-51-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 2-(4-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)phenyl)-6-amino-1H-benzo[d,e]isoquinoline-1,3(2H)-dione
• 英文别名: 6-Amino-2-[4-(1,4,7,10-tetraoxa-13-azacyclopentadec-13-yl)phenyl]benzo[de]isoquinoline-1,3-dione；6-amino-2-[4-(1,4,7,10-tetraoxa-13-azacyclopentadec-13-yl)phenyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1286630-51-0
• 化学式: C₂₈H₃₁N₃O₆
• 分子量: 505.571
• InChiKey: NRYISNZDERIFQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(4-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)phenyl)-6-amino-1H-benzo[d,e]isoquinoline-1,3(2H)-dione 在 高氯酸 作用下， 以 乙腈 为溶剂， 生成 2-(4-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)phenyl)-6-amino-1H-benzo[d,e]isoquinoline-1,3(2H)-dione bis(hydrogen perchlorate)
  参考文献：
  名称：

  Comparative analysis of the PET and ICT sensor properties of 1,8-naphthalimides containing aza-15-crown-5 ether moiety

  摘要：

  Novel 4-amino- and 4-(acetyl)amino-N-aryl-1,8-naphthalimides containing aza-15-crown-5 ether receptor unit in the N-aryl fragment and at C-4 of the naphthalimide residue were designed and prepared. Significant internal charge transfer from electron donating amino or amido group at C-4 of the naphthalene ring to the acceptor carboxyimide moiety as well as photoinduced electron transfer between N-aryl receptor and the naphthalimide fragment was revealed by the UV/Vis absorption spectroscopy and considerable fluorescence quenching. The addition of calcium perchlorate to an acetonitrile solution of naphthalimides with the receptor at imide nitrogen hindered the photoinduced electron transfer process and accordingly restored the quenched fluorescence of the free ligands. In the case of the compound in which the aza-15-crown-5 receptor is located at C-4, the coordination with Ca2+ reduced the internal charge transfer interaction in the chromophore and caused a significant blue-shift of the absorption and emission peak. The observed spectral effects were analyzed using PM6 semiempirical calculations. Formation of complexes was also confirmed by H-1 NMR spectroscopy. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.03.008
• 作为产物：
  描述：

  N-(4-aminophenyl)aza-15-crown-5 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 2-(4-(1,4,7,10-tetraoxa-13-azacyclopentadecan-13-yl)phenyl)-6-amino-1H-benzo[d,e]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Comparative analysis of the PET and ICT sensor properties of 1,8-naphthalimides containing aza-15-crown-5 ether moiety

  摘要：

  Novel 4-amino- and 4-(acetyl)amino-N-aryl-1,8-naphthalimides containing aza-15-crown-5 ether receptor unit in the N-aryl fragment and at C-4 of the naphthalimide residue were designed and prepared. Significant internal charge transfer from electron donating amino or amido group at C-4 of the naphthalene ring to the acceptor carboxyimide moiety as well as photoinduced electron transfer between N-aryl receptor and the naphthalimide fragment was revealed by the UV/Vis absorption spectroscopy and considerable fluorescence quenching. The addition of calcium perchlorate to an acetonitrile solution of naphthalimides with the receptor at imide nitrogen hindered the photoinduced electron transfer process and accordingly restored the quenched fluorescence of the free ligands. In the case of the compound in which the aza-15-crown-5 receptor is located at C-4, the coordination with Ca2+ reduced the internal charge transfer interaction in the chromophore and caused a significant blue-shift of the absorption and emission peak. The observed spectral effects were analyzed using PM6 semiempirical calculations. Formation of complexes was also confirmed by H-1 NMR spectroscopy. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.03.008

文献信息

• FRET versus PET: ratiometric chemosensors assembled from naphthalimide dyes and crown ethers
  作者：Pavel A. Panchenko、Yuri V. Fedorov、Olga A. Fedorova、Gediminas Jonusauskas

  DOI：10.1039/c5cp03510d

  日期：——

  Crown-containing naphthalimide dyads exhibited a ratiometric fluorescence response in the presence of metal cations and protons resulting from the competition between PET and FRET processes.

  含冠状物的萘酰亚胺二元化合物在金属阳离子和质子存在下表现出比例荧光响应，这是由于PET和FRET过程之间的竞争引起的。
• Hybrid sensor materials based on tin(IV) oxide and crown-containing 4-amino-1,8-naphthalimides
  作者：Pavel A. Panchenko、Yury V. Fedorov、Olga A. Fedorova、Boris A. Izmailov、Valery A. Vasnev、Vladislav V. Istratov、Ekaterina A. Makeeva、Marina N. Rumyantseva、Alexander M. Gaskov

  DOI：10.1016/j.mencom.2011.01.005

  日期：2011.1

  The cation-dependent spectral properties of crown-containing 4-aminonaphthalimide derivatives have been studied in an acetonitrile solution and within hybrid materials based on tin dioxide; these compounds can be of interest for producing fluorescent sensors for metal ions.
• Comparative analysis of the PET and ICT sensor properties of 1,8-naphthalimides containing aza-15-crown-5 ether moiety
  作者：Pavel A. Panchenko、Yuri V. Fedorov、Olga A. Fedorova、Gediminas Jonusauskas

  DOI：10.1016/j.dyepig.2013.03.008

  日期：2013.9

  Novel 4-amino- and 4-(acetyl)amino-N-aryl-1,8-naphthalimides containing aza-15-crown-5 ether receptor unit in the N-aryl fragment and at C-4 of the naphthalimide residue were designed and prepared. Significant internal charge transfer from electron donating amino or amido group at C-4 of the naphthalene ring to the acceptor carboxyimide moiety as well as photoinduced electron transfer between N-aryl receptor and the naphthalimide fragment was revealed by the UV/Vis absorption spectroscopy and considerable fluorescence quenching. The addition of calcium perchlorate to an acetonitrile solution of naphthalimides with the receptor at imide nitrogen hindered the photoinduced electron transfer process and accordingly restored the quenched fluorescence of the free ligands. In the case of the compound in which the aza-15-crown-5 receptor is located at C-4, the coordination with Ca2+ reduced the internal charge transfer interaction in the chromophore and caused a significant blue-shift of the absorption and emission peak. The observed spectral effects were analyzed using PM6 semiempirical calculations. Formation of complexes was also confirmed by H-1 NMR spectroscopy. (c) 2013 Elsevier Ltd. All rights reserved.