2,7-diaminotriptycene | 712343-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,7-diaminotriptycene
• 英文别名: pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),3,5,9(14),10,12,15,17,19-nonaene-4,12-diamine
• CAS: 712343-52-7
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: GZHKDBZWYOTANB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 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：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,7-diaminotriptycene 在 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 24.54h， 生成 2,7-bis((4-(tert-butyl)phenyl)ethynyl)-9,10-dihydro-9,10-[1,2]benzenoanthracene
  参考文献：
  名称：

  Synthesis and structures of Hexa-peri-hexabenzocoronene-based triptycenes

  摘要：

  A series of Hexa-peri-hexabenzocoronene-based triptycenes bearing mono-, di-, or tri-HBC moieties were synthesized from iodotriptycenes. Their structures were determined by NMR, MS spectra, and X-ray analysis. The planar HBC moieties displayed strong deshielding effect to triptycene scaffold, resulting in significant downfield chemical shift of the two methenyl protons. Moreover, the HBC units are well separated in the triptycene scaffold, without quenching the fluorescent properties of each HBC unit. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.085
• 作为产物：
  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

文献信息

• Aromatic single-walled organic nanotubes self-assembled from NH-bridged azacalix[2]triptycene[2]pyridine
  作者：Min Xue、Chuan-Feng Chen

  DOI：10.1039/c0cc04580b

  日期：——

  A novel triptycene-derived NH-bridged azacalixarene can self-assemble into an aromatic single-walled organic nanotube with large dimensions by four one-dimensional hydrogen bond chains.

  一种新颖的三茂萜衍生的NH桥氮杂硼硅芳烃可以通过四个一维氢键链自组装成具有大尺寸的芳香单壁有机纳米管。
• Hg2+ recognition by triptycene-derived heteracalixarenes: selectivity tuned by bridging heteroatoms and macrocyclic cavity
  作者：Shu-Zhen Hu、Chuan-Feng Chen

  DOI：10.1039/c1ob05515a

  日期：——

  The binding properties of triptycene-derived oxacalixarenes containing 1,8-naphthyridine subunits 1a and 1b toward metal ions were investigated in detail by spectroscopic methods. A couple of new N,O-bridged diazadioxacalixarenes 2a, 2b were synthesized and their binding properties to metal ions were also evaluated. The results showed that the oxacalixarene 1a, a cis-isomer with a boat-like 1,3-alternate conformation and a symmetrical cavity structure, exhibited a highly selective fluorescence response toward Hg2+ ions, while 1b, 2a and 2b did not show selective response towards any specific metal ions. Such selectivity can thus be controlled by the bridging heteroatoms and cavity structures of the macrocycles. Moreover, it was found that the fluorescence of 1a was considerably quenched upon the addition of Hg2+, and a 1 : 2 stoichiometry host–guest complex was proposed on the basis of the Job plot and 1H NMR titrations.

  通过光谱学方法详细研究了含有1,8-萘啶亚基1a和1b的三联苯衍生的氧杂杯芳烃对金属离子的结合特性。合成了几种新的N,O桥联二氮杂氧杂杯芳烃2a,2b，并评估了它们对金属离子的结合特性。结果表明，氧杂杯芳烃1a是一种具有船形1,3交替构象和对称空腔结构的顺式异构体，对Hg2+离子表现出高度选择性的荧光响应，而1b、2a和2b对任何特定金属离子均未表现出选择性响应。因此，这种选择性可以通过大环的桥联杂原子和空腔结构来控制。此外，发现1a的荧光在添加Hg2+后显着淬灭，并根据Job图和1H NMR滴定提出了1：2的化学计量主客体复合物。
• 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。