N,N'-bis{2-[2-[(2-bromo-2-methylpropanoyl)oxy]ethoxy]ethyl}perylene-3,4,9,10-tetracarboxylic acid bisimide | 1300740-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis{2-[2-[(2-bromo-2-methylpropanoyl)oxy]ethoxy]ethyl}perylene-3,4,9,10-tetracarboxylic acid bisimide
• 英文别名: 2-[2-[18-[2-[2-(2-Bromo-2-methylpropanoyl)oxyethoxy]ethyl]-6,8,17,19-tetraoxo-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-7-yl]ethoxy]ethyl 2-bromo-2-methylpropanoate；2-[2-[18-[2-[2-(2-bromo-2-methylpropanoyl)oxyethoxy]ethyl]-6,8,17,19-tetraoxo-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-7-yl]ethoxy]ethyl 2-bromo-2-methylpropanoate
• CAS: 1300740-62-8
• 化学式: C₄₀H₃₆Br₂N₂O₁₀
• 分子量: 864.541
• InChiKey: GDGQQSBXNWBCJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N,N'-bis(2-[2-hydroxyethoxy]ethyl)perylene-3,4,9,10-tetracarboxylic acid bisimide 、 2-溴-2-甲基丙酰溴 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 N,N'-bis{2-[2-[(2-bromo-2-methylpropanoyl)oxy]ethoxy]ethyl}perylene-3,4,9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  Functionalization of reduced graphene oxide nanosheets via stacking interactions with the fluorescent and water-soluble perylene bisimide-containing polymers

  摘要：

  Reduced graphene oxide (RGO)-polymer composites were prepared via pi-pi stacking interactions of RGO with the perylene bisimide-containing poly(glyceryl acrylate) (PBIPGA). PBIPGA was synthesized via atom transfer radical polymerization (ATRP) of solketal acrylate (SA), using bifunctional N,N'-bis(2-[2-[(2-bromo-2-methylpropanoyl)oxy]ethoxylethyl)perylene-3,4,9,10-tetracarboxylic acid bisimide (PBI-Br) as the initiator, and subsequent hydrolysis of the acetal-protecting group. PBIPGA was characterized by H-1 NMR spectroscopy, gel permeation chromatography (GPC). UV-visible absorption spectroscopy and fluorescence spectroscopy. The presence of pi-pi stacking interactions between PBI and the RGO surface was suggested by fluorescence and UV-visible absorption spectroscopy results. The chemical states pi-pi interaction, morphology, and composition of RGO-PBIPGA composites were characterized, respectively, by X-ray photoelectron spectroscopy (XPS), transmission electron microscopy (TEM) and thermogravimetric analysis (TGA). The low cytotoxicity level of the RGO-PBIPGA composites was revealed by incubation with 3T3 fibroblasts in 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assays in vitro. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.03.054

文献信息

• A highly fluorescent cationic bifunctional conjugate
  作者：X. C. Yang、M. Y. Chai、Y. Zhu、W. T. Yang、F. J. Xu

  DOI：10.1039/c2jm16166d

  日期：——

  It was of crucial importance to modify perylene-3,4,9,10-tetracarboxylic acid bisimides (PBIs) for the design of new perylene-based bio-dye agents with strong fluorescence. Recently, we reported that ethanolamine (EA)-functionalized poly(glycidyl methacrylate) (or PGEA) can produce good transfection efficiency, while exhibiting very low toxicity. Herein, the low-toxic PGEA was proposed to be conjugated with PBIs via facile atom transfer radical polymerization for the well-defined highly fluorescent cationic bifunctional conjugate (PBI–PGEA). The obtained PBI–PGEA exhibited good water-solubility properties, characteristic spectroscopic patterns of PBIs, and excellent photostability. The PBI–PGEA conjugate can be used as an efficient cell bio-dye for rapid (2–5 min) cell labeling at low concentrations (0.06–0.12 mg mL−1). Such a fast labeling process did not induce obvious cytotoxicity, avoiding possible side-effects to the cells. In addition, the PBI–PGEA still possessed good gene transfection efficiency in different cell lines. With the strong fluorescence in water and good transfection properties, the developed bifunctional PBI–PGEA should possess more potential in bioimaging and gene delivery.

  修改苯并[a]蒽-3,4,9,10-四乙酸二酰亚胺（PBI）对于设计具有强荧光的新型苯并[a]蒽基生物染料至关重要。最近，我们报道了功能化的聚（甘油醚甲基丙烯酸酯）（PGEA）能产生良好的转染效率，同时表现出非常低的毒性。在此，低毒性的PGEA提议通过简便的原子转移自由基聚合与PBI结合，形成具有良好定义的高荧光阳离子双功能结合物（PBI–PGEA）。所获得的PBI–PGEA表现出良好的水溶性、PBI的特征光谱模式和优异的光稳定性。PBI–PGEA结合物可以作为高效的细胞生物染料，在低浓度（0.06–0.12 mg mL−1）下实现快速（2-5分钟）细胞标记。这一快速标记过程未引起明显的细胞毒性，避免了对细胞可能产生的副作用。此外，PBI–PGEA在不同细胞系中仍具备良好的基因转染效率。凭借在水中强荧光和良好的转染特性，开发的双功能PBI–PGEA在生物成像和基因传递方面应具有更大的潜力。
• Functionalization of reduced graphene oxide nanosheets via stacking interactions with the fluorescent and water-soluble perylene bisimide-containing polymers
  作者：Li Qun Xu、Liang Wang、Bin Zhang、Chee Hong Lim、Yu Chen、Koon-Gee Neoh、En-Tang Kang、Guo Dong Fu

  DOI：10.1016/j.polymer.2011.03.054

  日期：2011.5

  Reduced graphene oxide (RGO)-polymer composites were prepared via pi-pi stacking interactions of RGO with the perylene bisimide-containing poly(glyceryl acrylate) (PBIPGA). PBIPGA was synthesized via atom transfer radical polymerization (ATRP) of solketal acrylate (SA), using bifunctional N,N'-bis(2-[2-[(2-bromo-2-methylpropanoyl)oxy]ethoxylethyl)perylene-3,4,9,10-tetracarboxylic acid bisimide (PBI-Br) as the initiator, and subsequent hydrolysis of the acetal-protecting group. PBIPGA was characterized by H-1 NMR spectroscopy, gel permeation chromatography (GPC). UV-visible absorption spectroscopy and fluorescence spectroscopy. The presence of pi-pi stacking interactions between PBI and the RGO surface was suggested by fluorescence and UV-visible absorption spectroscopy results. The chemical states pi-pi interaction, morphology, and composition of RGO-PBIPGA composites were characterized, respectively, by X-ray photoelectron spectroscopy (XPS), transmission electron microscopy (TEM) and thermogravimetric analysis (TGA). The low cytotoxicity level of the RGO-PBIPGA composites was revealed by incubation with 3T3 fibroblasts in 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assays in vitro. (C) 2011 Elsevier Ltd. All rights reserved.