2,3,6,7,14,15-六氨基三蝶烯 | 58519-07-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 2,3,6,7,14,15-六氨基三蝶烯
• 英文名称: 2,3,6,7,14,15-hexaaminotriptycene
• 英文别名: hexaaminotriptycene；2,3,6,7,12,13-Hexaminotriptycen；2,3,6,7,14,15-Hexaaminotriptycene hexahydrochloride；pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-4,5,11,12,17,18-hexamine
• CAS: 58519-07-6
• 化学式: C₂₀H₂₀N₆
• 分子量: 344.419
• InChiKey: VDOXJAQJMWQJDF-UHFFFAOYSA-N

物化性质

• 熔点：
  181-184 °C (decomp)
• 沸点：
  644.6±55.0 °C(Predicted)
• 密度：
  1.523±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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：
  156
• 氢给体数：
  6
• 氢受体数：
  6

制备方法与用途

概述

2,3,6,7,14,15-六氨基三蝶烯可用作医药合成的中间体。这种化合物不仅拥有独特的刚性结构，在空间自由体积方面也表现出色，使其成为合成自具微孔聚合物的良好单体。近年来，基于三蝶烯结构的共轭聚合物、芳香聚酯等不断被开发出来，并取得了广泛的应用。然而，通过化学法脱水制备聚酰亚胺并用于分离膜的制备，目前尚未见相关专利报道。

用途

2,3,6,7,14,15-六氨基三蝶烯作为一种烃类衍生物，主要用于有机合成原料。

反应信息

• 作为反应物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 2,3,6,7,14,15-六氨基三蝶烯 以 乙醇 为溶剂， 反应 18.0h， 以54%的产率得到5,11,14,20,28,34,37,43,50,56,59,65-Dodecazaheptadecacyclo[22.22.22.02,23.04,21.06,19.07,12.013,18.025,46.027,44.029,42.030,35.036,41.047,68.049,66.051,64.052,57.058,63]octahexaconta-2,4(21),5,7(12),8,10,13(18),14,16,19,22,25,27(44),28,30(35),31,33,36(41),37,39,42,45,47,49(66),50,52(57),53,55,58(63),59,61,64,67-tritriacontaene
  参考文献：
  名称：

  Molecular Scaffolding of Prussian Blue Analogues Using a Phenanthroline-Extended Triptycene Ligand

  摘要：

  Shape-persistent ligands with triptycene groups are promising candidates for the development of porous metal-organic frameworks with functional surface area. In this work, a series of phenanthroline-extended triptycene compounds was synthesized and used as structure-directing ligands for the fabrication of a triptycene-scaffolded Prussian blue analogue. The ligands were reacted with K(3)[Fe(CN)(6)] and CuCl(2) under hydrothermal conditions to afford two new clathrates: a coordination compound of (triptycenyl phenanthroline) copper(I) and an infinite one-dimensional zigzag coordination polymer of copper cyanide scaffolded by phenanthroline-extended triptycenes. These structures illustrate the potential for the triptycene-functionalized ligands to provide access to materials with interesting architectures.

  DOI：

  10.1021/cg200788f
• 作为产物：
  描述：

  2,3,6,7,14,15-hexanitrotriptycene 在 镍 一水合肼 作用下， 生成 2,3,6,7,14,15-六氨基三蝶烯
  参考文献：
  名称：

  Shalaev,V.K. et al., Journal of Organic Chemistry USSR (English Translation), 1976, vol. 12, p. 185 - 190

  摘要：

  DOI：

文献信息

• Synthesis and Structures of 1,10-Phenanthroline-Based Extended Triptycene Derivatives
  作者：Chuan-Feng Chen、Yi Jiang

  DOI：10.1055/s-0029-1219957

  日期：2010.7

  A series of novel 1,10-phenanthroline-based extended triptycene derivatives were conveniently synthesized in good yields, and their structures were determined by ¹H NMR, ¹³C NMR, MALDI-TOF MS spectra, and elemental analysis.

  通过¹H NMR、¹³C NMR、MALDI-TOF MS 光谱和元素分析确定了它们的结构。
• High CO₂uptake and selectivity by triptycene-derived benzimidazole-linked polymers
  作者：Mohammad Gulam Rabbani、Thomas E. Reich、Refaie M. Kassab、Karl T. Jackson、Hani M. El-Kaderi

  DOI：10.1039/c2cc16986j

  日期：——

  Successful incorporation of triptycene into benzimidazole-linked polymers leads to the highest CO2 uptake (5.12 mmol g−1, 273 K and 1 bar) by porous organic polymers and results in high CO2/N2 (63) and CO2/CH4 (8.4) selectivities.

  将三蝶烯成功掺入苯并咪唑连接的聚合物中，可使多孔有机聚合物吸收最高的 CO2（5.12 mmol g−1、273 K 和 1 bar），并产生高 CO2/N2 (63) 和 CO2/CH4 (8.4) 选择性。
• Towards a self-assembled honeycomb structure via diaminotriptycene metal complexes
  作者：Qian Liang、Jonathan H. Chong、Nicholas G. White、Zhen Zhao、Mark J. MacLachlan

  DOI：10.1039/c3dt51330k

  日期：——

  We illustrate a new approach toward the synthesis of a porous supramolecular honeycomb based on triptycene. A coordination polymer has been prepared where the triptycene groups are linked through triptycenesemiquinonediimine platinum complexes, but the product is disordered rather than the intended honeycomb structure. A model platinum complex and its 15N-labeled isotopomer have been prepared and characterized.

  我们展示了一种基于三庚烯合成多孔超分子蜂窝的新方法。我们制备了一种配位聚合物，其中的三庚烯基团通过三庚烯-泛醌二亚胺铂络合物连接，但产物是无序的，而不是预期的蜂窝结构。我们制备了一种模型铂络合物及其 15N 标记的异构体，并对其进行了表征。
• Synthesis and Structural Investigation of New Triptycene-Based Ligands:  En Route to Shape-Persistent Dendrimers and Macrocycles with Large Free Volume
  作者：Jonathan H. Chong、Mark J. MacLachlan

  DOI：10.1021/jo701297q

  日期：2007.11.1

  Triptycene was used to build a series of ligands containing pyrazine groups for use in forming coordination frameworks and as model compounds toward target shape-persistent dendrimers and macrocycles. The phenylenediamine precursors are formed by controlled double nitration/reduction of triptycene, followed by condensation with triptycenyl o-quinone to form the ligands. Solid-state structures show

  三萜被用于构建一系列含有吡嗪基团的配体，用于形成配位骨架，并作为朝向目标形状持久性树枝状大分子和大环的模型化合物。苯二胺前体是通过控制三硝烯的双硝化/还原，然后与三蝶烯基邻醌缩合形成配体而形成的。固态结构表明，配体有利于堆积在具有分子间π堆积的层状结构中。增加翼的长度仍然可以有效地包装，但是增加吡嗪基团的数量或增加更多的三蝶烯基部分会降低包装效率。为了展示这些分子作为配体发挥作用的潜力，其配位复合物为15 得到碘化亚铜（I），并发现其形成堆积成分层排列的二聚体。
• ORGANIC TRIPTYCENE-BASED MOLECULES HAVING ONE OR MORE ARYLENE DIIMIDE GROUPS ATTACHED FORMING A CROSSLINKED FRAMEWORK USEFUL FOR LITHIUM ION BATTERY ELECTRODES
  申请人：THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO

  公开号：US20210167388A1

  公开（公告）日：2021-06-03

  The present disclosure relates to electroactive materials that are useful for secondary battery electrode materials and the secondary battery device including thereof. Further, the disclosure relates to cathode and anode materials obtained via the polymerization of triptycene-based organic molecules having one or more arylene diimide groups attached forming a crosslinked network.