6-bromo-2-(naphthalen-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 114001-59-1

• 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: 6-bromo-2-(naphthalen-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 6-bromo-2-naphthalen-1-ylbenzo[de]isoquinoline-1,3-dione
• CAS: 114001-59-1
• 化学式: C₂₂H₁₂BrNO₂
• 分子量: 402.247
• InChiKey: SKYMKNCXMMJSLC-UHFFFAOYSA-N

物化性质

• 沸点：
  623.6±47.0 °C(predicted)
• 密度：
  1.601±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-2-(naphthalen-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 、 N-苯基-2-萘胺 在 三叔丁基膦 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以74%的产率得到(N-naphthyl)-4-[N-(naphthalene-2-yl)-N-phenylamino]-1,8-naphthalimide
  参考文献：
  名称：

  A New Orange-Light-Emitting Materials Based on (N-naphthyl)-1,8-naphthalimide for OLED Applications

  摘要：

  A new orange emitters consisting of 2-naphthalene-1-yl-benzo[de]isoquinoline-1, 3-dione (NBID) as core, and bulky diphenylamine or naphthylphenylamine substituted as a side units were synthesized and characterized. These compounds have a non-planar molecule conformation, donor-acceptor structure, and high thermal stability. Using these materials as dopant, we fabricated electroluminescence device with a structure of ITO/DNTPD/NPD/NBID-1, 2 (3 wt% in Alq(3))/Alq(3)/LiF/Al. The luminance-efficiency of NBID derivatives (1 and 2) were showed 6.6 cd/A and 5.9 cd/A, respectively. The orange emissions were observed with Commission International de I'Eclairage (CIE) coordinates of (0.46, 0.52) for NBID-1 and (0.48, 0.52) for NBID-2, respectively.

  DOI：

  10.1080/15421400903217751
• 作为产物：
  描述：

  4-溴-1,8-萘二甲酸酐 、 1-萘胺 在 溶剂黄146 作用下， 反应 24.0h， 以65%的产率得到6-bromo-2-(naphthalen-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Suzuki反应†包含2,4,6-三苯基吡啶和1,8-萘二甲酰亚胺单元的新型荧光材料的合成和光物理性质†

  摘要：

  使用Suzuki偶联反应已以高收率制备了一系列含有1,8-萘二甲酰亚胺基团的新型2,4,6-三苯基吡啶衍生物。通过热重分析仪，紫外可见光，荧光和电化学分析仪系统地研究了化合物的光致发光性能之间的关系。

  DOI：

  10.1039/c6ra16408k

文献信息

• Synthesis and optical properties of novel compounds containing carbazole and 1, 8-naphthalimide groups
  作者：Guo-Liang Feng、Shun-Jun Ji、Li-Jun Geng、Bing Bian、Yu Liu

  DOI：10.3184/030823408x304041

  日期：2008.3

  A series of novel carbazole-naphthalimide compounds with moieties capable of carrier-balance and electroluminescence were synthesised and characterised, and theirs luminescent properties had been studied.

  合成并表征了一系列具有载流子平衡和电致发光结构的新型咔唑-萘二甲酰亚胺化合物，并研究了它们的发光性能。
• 10.1007/s10895-024-03903-6
  作者：Palanisamy, Jayasudha、Rajagopal, Rajakrishnan、Alfarhan, Ahmed

  DOI：10.1007/s10895-024-03903-6

  日期：——

  spectroscopy techniques. The NAP probe was exposed to a solvatochromic and aggregation-induced emission (AIE) probe using UV-visible and PL spectroscopy. In this case, the increased polarity of the solvent shows that it is red-shifted. The probe emission, a sky blue to yellow-green color at hexane to DCM, exhibited an excellent quantum yield. Meanwhile, the high-polar solvents of DMF and DMSO had poor quantum

  成功合成了萘酰亚胺分子（ NAP ）并通过光谱技术对其进行了表征。使用紫外可见光和 PL 光谱将NAP探针暴露于溶剂化变色和聚集诱导发射 (AIE) 探针。在这种情况下，溶剂极性的增加表明它发生了红移。在己烷至 DCM 下，探针发射出天蓝色至黄绿色，表现出优异的量子产率。同时，DMF和DMSO等高极性溶剂的量子产率较差。该探针NAP显示聚集诱导发射特性显着增强了f w = 80–90% 的发射（在 540 nm 处）。 NAP 使用己烷和氯仿中的两种极性溶剂蒸气进行，以在进一步的固态研究中研究 VOC。制备了真实试纸套件NAP探针，并研究了己烷和氯仿的 VOC 检测。当暴露于己烷蒸气时， NAP探针测试套件在紫外光下显示天蓝色发射，暴露于氯仿后恢复为绿色发射。因此，结果表明该NAP探头可用于气体泄漏检测应用。
• Synthesis and photophysical properties of novel fluorescent materials containing 2,4,6-triphenylpyridine and 1,8-naphthalimide units using Suzuki reaction
  作者：Hui-Yan Liu、Liang-Feng Chen、Hai-Ying Wang、Yu Wan、Hui Wu

  DOI：10.1039/c6ra16408k

  日期：——

  A series of novel 2,4,6-triphenylpyridine derivatives containing 1,8-naphthalimide groups have been prepared in good yields using Suzuki couplings reactions. The relationship of the photoluminescence property of the compounds was systematically investigated via a thermogravimetric analyzer, UV-vis, fluorescence and electrochemical analyzer.

  使用Suzuki偶联反应已以高收率制备了一系列含有1,8-萘二甲酰亚胺基团的新型2,4,6-三苯基吡啶衍生物。通过热重分析仪，紫外可见光，荧光和电化学分析仪系统地研究了化合物的光致发光性能之间的关系。
• A New Orange-Light-Emitting Materials Based on (N-naphthyl)-1,8-naphthalimide for OLED Applications
  作者：Sung Ouk Jung、Wei Yuan、Jin Uk Ju、Shuang Zhang、Yun Hi Kim、Jong Tae Je、Soon Ki Kwon

  DOI：10.1080/15421400903217751

  日期：2009.11.11

  A new orange emitters consisting of 2-naphthalene-1-yl-benzo[de]isoquinoline-1, 3-dione (NBID) as core, and bulky diphenylamine or naphthylphenylamine substituted as a side units were synthesized and characterized. These compounds have a non-planar molecule conformation, donor-acceptor structure, and high thermal stability. Using these materials as dopant, we fabricated electroluminescence device with a structure of ITO/DNTPD/NPD/NBID-1, 2 (3 wt% in Alq(3))/Alq(3)/LiF/Al. The luminance-efficiency of NBID derivatives (1 and 2) were showed 6.6 cd/A and 5.9 cd/A, respectively. The orange emissions were observed with Commission International de I'Eclairage (CIE) coordinates of (0.46, 0.52) for NBID-1 and (0.48, 0.52) for NBID-2, respectively.