4,4’-dicarboxyazobenzene bis(N-hydroxysuccinimide ester) | 1256247-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4,4’-dicarboxyazobenzene bis(N-hydroxysuccinimide ester)
• 英文别名: 4,4'-bis(2,5-dioxo-pyrrolidin-1-yl ester)azobenzene；Bis(2,5-dioxopyrrolidin-1-yl) 4,4'-(diazene-1,2-diyl)dibenzoate；(2,5-dioxopyrrolidin-1-yl) 4-[[4-(2,5-dioxopyrrolidin-1-yl)oxycarbonylphenyl]diazenyl]benzoate
• CAS: 1256247-73-0
• 化学式: C₂₂H₁₆N₄O₈
• 分子量: 464.391
• InChiKey: KUNLIVAVPAQHKP-UHFFFAOYSA-N

物化性质

• 沸点：
  665.3±65.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,4’-dicarboxyazobenzene bis(N-hydroxysuccinimide ester) 在 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 C₄₀H₃₆N₈O₁₂S₂
  参考文献：
  名称：

  Small‐Molecule‐based Supramolecular Plastics Mediated by Liquid‐Liquid Phase Separation**

  摘要：

  AbstractPlastics are one of the most widely used polymeric materials. However, they are often undegradable and non‐recyclable due to the very stable covalent bonds of macromolecules, causing environmental pollution and health problems. Here, we report that liquid‐liquid phase separation (LLPS) could drive the formation of robust, stable, and sustainable plastics using small molecules. The LLPS process could sequester and concentrate solutes, strengthen the non‐covalent association between molecules and produce a bulk material whose property was highly related to the encapsulated water amounts. It was a robust plastic with a remarkable Young's modulus of 139.5 MPa when the water content was low while became adhesive and could instantly self‐heal with more absorbed water. Finally, responsiveness enabled the material to be highly recyclable. This work allowed us to understand the LLPS at the molecular level and demonstrated that LLPS is a promising approach to exploring eco‐friendly supramolecular plastics that are potential substitutes for conventional polymers.

  DOI：

  10.1002/anie.202204611
• 作为产物：
  描述：

  对硝基苯甲酸 在 4-二甲氨基吡啶 、 2,3,4,5,6-pentahydroxy-hexanal 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4,4’-dicarboxyazobenzene bis(N-hydroxysuccinimide ester)
  参考文献：
  名称：

  Small‐Molecule‐based Supramolecular Plastics Mediated by Liquid‐Liquid Phase Separation**

  摘要：

  AbstractPlastics are one of the most widely used polymeric materials. However, they are often undegradable and non‐recyclable due to the very stable covalent bonds of macromolecules, causing environmental pollution and health problems. Here, we report that liquid‐liquid phase separation (LLPS) could drive the formation of robust, stable, and sustainable plastics using small molecules. The LLPS process could sequester and concentrate solutes, strengthen the non‐covalent association between molecules and produce a bulk material whose property was highly related to the encapsulated water amounts. It was a robust plastic with a remarkable Young's modulus of 139.5 MPa when the water content was low while became adhesive and could instantly self‐heal with more absorbed water. Finally, responsiveness enabled the material to be highly recyclable. This work allowed us to understand the LLPS at the molecular level and demonstrated that LLPS is a promising approach to exploring eco‐friendly supramolecular plastics that are potential substitutes for conventional polymers.

  DOI：

  10.1002/anie.202204611

文献信息

• Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer
  作者：Florian Hamon、Claire Blaszkiewicz、Marie Buchotte、Estelle Banaszak-Léonard、Hervé Bricout、Sébastien Tilloy、Eric Monflier、Christine Cézard、Laurent Bouteiller、Christophe Len、Florence Djedaini-Pilard

  DOI：10.3762/bjoc.10.304

  日期：——

  This paper reports an efficient preparation of bridged bis-β-CD AZO-CDim 1 bearing azobenzene as a linker and exhibiting high solubility in water. The photoisomerization properties were studied by UV–vis and HPLC and supported by ab initio calculations. The cis/trans ratio of AZO-CDim 1 is 7:93 without irradiation and 37:63 after 120 min of irradiation at 365 nm; the reaction is reversible after irradiation at 254 nm. The photoinduced, switchable binding behavior of AZO-CDim 1 was evaluated by ITC, NMR and molecular modeling in the presence of a ditopic adamantyl guest. The results indicate that AZO-CDim 1 can form two different inclusion complexes with an adamantyl dimer depending on its photoinduced isomers. Both cavities of cis-AZO-CDim 1 are complexed simultaneously by two adamantyl units of the guest forming a 1:1 complex while trans-AZO-CDim 1 seems to lead to the formation of supramolecular polymers with an n:n stoichiometry.

  这篇论文报告了一种有效的桥式双β-CD AZO-CDim 1的制备方法，其中含有偶氮苯作为连接剂，并在水中具有高溶解度。通过UV-vis和HPLC进行了光异构化性能研究，并通过从头计算进行了支持。未经照射时，AZO-CDim 1的顺/反比为7:93，在365 nm照射120分钟后为37:63；254 nm照射后反应可逆。在存在二元脂肪环客体的情况下，通过ITC、NMR和分子建模评估了AZO-CDim 1的光诱导可切换结合行为。结果表明，AZO-CDim 1可以形成两种不同的包含复合物，取决于其光诱导异构体。顺-AZO-CDim 1的两个腔同时与两个客体的脂肪环单体形成1:1复合物，而反-AZO-CDim 1似乎导致与n:n化学计量比的超分子聚合物形成。
• Liu, Dingbin; Xie, Yunyan; Shao, Huawu, Angewandte Chemie - International Edition, 2009, vol. 48, p. 4406 - 4408
  作者：Liu, Dingbin、Xie, Yunyan、Shao, Huawu、Jiang, Xingyu

  DOI：——

  日期：——