2,7-dinitrotriptycene | 42810-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,7-dinitrotriptycene
• 英文别名: 2,7-Dinitro-triptycen；4,12-Dinitropentacyclo[6.6.6.0(2,7).0(9,14).0(15,20)]icosa-2,4,6,9,11,13,15,17,19-nonaene；4,12-dinitropentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),3,5,9(14),10,12,15,17,19-nonaene
• CAS: 42810-43-5
• 化学式: C₂₀H₁₂N₂O₄
• 分子量: 344.326
• InChiKey: QHVDBHFJKHPWSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-dinitrotriptycene 在 palladium on activated charcoal 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以40.5%的产率得到2,7-diaminotriptycene
  参考文献：
  名称：

  Enhanced Gas Separation Properties of Tröger’s Base Polymer Membranes Derived from Pure Triptycene Diamine Regioisomers

  摘要：

  Most high-performance Troger's base (TB) polymers for gas separation membranes are from mixed diamine isomers, and the configuration differences in the polymer chain packing that arise from these isomers are still unknown. Herein three triptycene-containing Troger's-base-based polymers, CTTB (from pure Trip-2,6-diamine), MTTB (from pure Trip-2,7-diamine), and ITTB (from 50/50 Trip-2,6-diamine/Trip-2,7-diamine mixed regioisomers), were successfully synthesized and fully characterized. All polymers exhibited high thermal stability and rigidity, a large Brunauer-Emmett-Teller surface area, and distinct microporosity (pores <20 angstrom). ITTB showed the largest pores (ITTB (6.25 angstrom) > MTTB (6.15 angstrom) > CTTB (5.68 A)) and pore-size distributions (ITTB (6.14-8.0 angstrom) > CTTB (5.48-7.0 angstrom) > MTTB (6.09-6.90 angstrom)). MTTB and CTTB showed outstanding H-2/CH4, H-2/N-2, and O-2/N-2 separation performance that successfully surpassed the 2015 trade-off curves, better than those of the most recently reported state-of-the-art gas separation membranes and ITTB, due to their more uniform polymer main chain arrangement. This result shed light on the future high-performance gas separation polymer designs.

  DOI：

  10.1021/acs.macromol.9b02328
• 作为产物：
  描述：

  三蝶烯 在 硝酸乙酸酐 、 乙酸酐 、 溶剂黄146 作用下， 生成 2,7-dinitrotriptycene
  参考文献：
  名称：

  Electron spin resonance studies of bicyclo[2.2.1]heptanes and bicyclo[2.2.2]octanes spin labeled with nitrobenzene anion radicals

  摘要：

  DOI：

  10.1021/ja00796a033

文献信息

• Azobenzene‐Substituted Triptycenes: Understanding the Exciton Coupling of Molecular Switches in Close Proximity
  作者：Anne Kunz、Nils Oberhof、Frederik Scherz、Leon Martins、Andreas Dreuw、Hermann A. Wegner

  DOI：10.1002/chem.202200972

  日期：2022.7.6

  Switchable host system: Azobenzenes have been attached to a triptycene scaffold in the meta position. Isomerization experiments revealed efficient switching of azobenzene moieties together with the build-up of a cavity in the all-Z conformation of the C3v-symmetric trisazobenzene-triptycene; this makes this molecule interesting as a switchable host system. Moreover, computational studies indicated

  可切换的宿主系统：偶氮苯已连接到间位的三蝶烯支架上。异构化实验揭示了偶氮苯部分的有效转换以及C 3v对称三偶氮苯-三蝶烯的全Z构象中空腔的建立；这使得这种分子作为一个可切换的宿主系统很有趣。此外，计算研究表明激子耦合导致 π-π* 激发的不同跃迁概率。
• Homoconjugation and Tautomeric Isomerism in Triptycene-Fused Pyridylbenzimidazoles
  作者：Giovanni Preda、Riccardo Mobili、Davide Ravelli、Valeria Amendola、Dario Pasini

  DOI：10.1021/acs.joc.4c00221

  日期：2024.4.19

  The facile, metal-free synthesis and characterization of three new series of triptycene-fused pyridylbenzimidazoles are reported; such compounds possess an imidazole moiety fused within the benzene rings of the trypticene and a pyridine ring installed at position 2 of the imidazole rings. The position of the nitrogen atom of the pyridyl moiety linked to position 2 of the fused benzimidazole scaffold

  报告了三个新系列三蝶烯稠合吡啶基苯并咪唑的简便、无金属合成和表征；此类化合物具有稠合在色烯的苯环内的咪唑部分和安装在咪唑环的2位上的吡啶环。连接到稠合苯并咪唑骨架的2位的吡啶基部分的氮原子的位置系统地从邻位变为对位。带有吡啶基取代的稠合苯并咪唑支架的取代叶片的数量已从一个增加到三个。这样的化合物库使我们能够评估两种主要效应的增强：互变异构现象和同源共轭。通过1 H 核磁共振波谱检查了由质子互变引起的不同异构体之间的特征动态平衡。通过将新化合物与经典平面吡啶基苯并咪唑的光物理性质进行比较，证明了不同三蝶烯叶片之间存在同共轭效应。通过计算分析揭示了新衍生物电子结构的细节。这些新型化合物可用于构建有趣的自组装超分子结构。
• Electron spin resonance studies of bicyclo[2.2.1]heptanes and bicyclo[2.2.2]octanes spin labeled with nitrobenzene anion radicals
  作者：Shigeru. Terabe、Ryusei. Konaka

  DOI：10.1021/ja00796a033

  日期：1973.7
• Enhanced Gas Separation Properties of Tröger’s Base Polymer Membranes Derived from Pure Triptycene Diamine Regioisomers
  作者：Zhiyang Zhu、Junjie Zhu、Jianxin Li、Xiaohua Ma

  DOI：10.1021/acs.macromol.9b02328

  日期：2020.3.10

  Most high-performance Troger's base (TB) polymers for gas separation membranes are from mixed diamine isomers, and the configuration differences in the polymer chain packing that arise from these isomers are still unknown. Herein three triptycene-containing Troger's-base-based polymers, CTTB (from pure Trip-2,6-diamine), MTTB (from pure Trip-2,7-diamine), and ITTB (from 50/50 Trip-2,6-diamine/Trip-2,7-diamine mixed regioisomers), were successfully synthesized and fully characterized. All polymers exhibited high thermal stability and rigidity, a large Brunauer-Emmett-Teller surface area, and distinct microporosity (pores <20 angstrom). ITTB showed the largest pores (ITTB (6.25 angstrom) > MTTB (6.15 angstrom) > CTTB (5.68 A)) and pore-size distributions (ITTB (6.14-8.0 angstrom) > CTTB (5.48-7.0 angstrom) > MTTB (6.09-6.90 angstrom)). MTTB and CTTB showed outstanding H-2/CH4, H-2/N-2, and O-2/N-2 separation performance that successfully surpassed the 2015 trade-off curves, better than those of the most recently reported state-of-the-art gas separation membranes and ITTB, due to their more uniform polymer main chain arrangement. This result shed light on the future high-performance gas separation polymer designs.