amine/phenyl-capped tetraaniline | 2908-00-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: amine/phenyl-capped tetraaniline
• 英文别名: tetraaniline；AT；<1,4>Benzochinon-(4-amino-phenylimin)-(4-anilino-phenylimin)；[1,4]Benzochinon-(4-amino-phenylimin)-(4-anilino-phenylimin)；4-[[4-(4-Anilinophenyl)iminocyclohexa-2,5-dien-1-ylidene]amino]aniline
• CAS: 2908-00-1
• 化学式: C₂₄H₂₀N₄
• 分子量: 364.45
• InChiKey: OFUPGLJDIUBZTA-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  545.9±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  amine/phenyl-capped tetraaniline 在 一水合肼 作用下， 反应 24.0h， 生成 aniline tetramer
  参考文献：
  名称：

  Synthesis and spectroscopic properties of aniline tetramers. Comparative studies

  摘要：

  我们开发出了一种新的合成方法，即先将 4-氟硝基苯与芳基胺进行 SNAr 偶联，然后再还原硝基。通过这种方法制备了两种类型的苯胺低聚物，即 Ph/NH2 和 NH2/NH2 四聚物。通过核磁共振、紫外-可见-近红外光谱、红外光谱和质谱分析，对处于白绿宝石氧化态和绿宝石氧化态的四聚体进行了表征。结果表明，氧化成绿宝石态的 NH2/NH2 四聚体会形成两种异构体：同步异构体和反同步异构体。Ph/NH2 四聚体的氧化会产生位置异构体，具体取决于合成方法。

  DOI：

  10.1039/b311096f
• 作为产物：
  描述：

  对氨基二苯胺 在 盐酸 、 水 、 三氯化铁 作用下， 反应 2.0h， 生成 amine/phenyl-capped tetraaniline
  参考文献：
  名称：

  以六硝基[60]富勒烯为前驱体合成爆炸形六（低聚苯胺化）C 60

  摘要：

  使用六硝基[60]富勒烯（HNF）作为反应性前体分子，证明了爆星型六苯胺基，六（二苯胺基），六（四苯胺基）和六（六癸基苯胺基）[60]富勒烯（HHDAF）的有效合成。发现HNF的叔硝基基团是优异的离去基团，可被亲核取代基取代。利用这种与电子给体亲核试剂的反应性，开发了一种合成方法来生产寡苯胺化富勒烯，作为分子内给体-受体A-（D）6具有明确定义的臂数和链长的星爆大分子。HNF与低聚苯胺的反应性随重复苯胺单元数量的增加而增加。在温和条件下与HNF完全反应只需要等摩尔量的四苯胺和十六苯胺即可。在1 H NMR光谱上对材料的质子数进行定量测量，可用于确定低聚苯胺化富勒烯组合物中每C 60的加成数。结果，NMR数据与四苯胺基化和十六烷基苯胺化的富勒烯的结构非常吻合，每个C 60分别含有6个四苯胺基和十六烷基苯胺基臂。DCI也支持HHDAF的这一组成部分–-MS光谱数据显示了碎片化的低聚苯胺基质量离

  DOI：

  10.1039/a905393j

文献信息

• Nanoscale Morphology, Dimensional Control, and Electrical Properties of Oligoanilines
  作者：Yue Wang、Henry D. Tran、Lei Liao、Xiangfeng Duan、Richard B. Kaner

  DOI：10.1021/ja1014184

  日期：2010.8.4

  Here, we report a general method for producing a variety of oligoaniline nanostructures with well-defined morphologies and dimensionalities. 1-D nanowires, 2-D nanoribbons, and 3-D rectangular nanoplates and nanoflowers of tetraaniline are produced by a solvent exchange process in which the dopant acid can be used to tune the oligomer morphology. The process appears to be a general route for producing

  虽然近年来有机导体的纳米结构引起了极大的兴趣，但它们的纳米尺寸和形状控制仍然是一个重大挑战。在这里，我们报告了一种生产各种具有明确形态和维度的低聚苯胺纳米结构的通用方法。四苯胺的 1-D 纳米线、2-D 纳米带和 3-D 矩形纳米板和纳米花是通过溶剂交换过程生产的，其中掺杂酸可用于调整低聚物形态。该过程似乎是为各种其他苯胺低聚物（如苯基封端的四聚体）生产纳米结构的一般途径。四苯胺纳米结构的 X 射线衍射表明它们具有不同的堆积排列，这导致不同的纳米级形态具有不同的结构电特性。单个四苯胺纳米结构的电导率比先前报道的最高值高出 2 个数量级，可与传统的掺酸聚苯胺压片相媲美。此外，这些低聚物纳米结构可以通过多种方法轻松加工，以在宏观区域上形成由排列的纳米结构组成的薄膜。
• Synthesis of starburst hexa(oligoanilinated) C60 using hexanitro[60]fullerene as a precursor
  作者：Vijayaraj Anantharaj、Lee Y. Wang、Taizoon Canteenwala、Long Y. Chiang

  DOI：10.1039/a905393j

  日期：——

  proton counts over the 1H NMR spectrum was utilized for determining the number of addends per C60 in the composition of oligoanilinated fullerenes. As a result, the NMR data fits well with the structure of tetraanilinated and hexadecaanilinated fullerenes, containing 6 tetraanilino and hexadecaanilino arms per C60, respectively. This composition of HHDAF was also supported by the DCI–-MS spectroscopic data

  使用六硝基[60]富勒烯（HNF）作为反应性前体分子，证明了爆星型六苯胺基，六（二苯胺基），六（四苯胺基）和六（六癸基苯胺基）[60]富勒烯（HHDAF）的有效合成。发现HNF的叔硝基基团是优异的离去基团，可被亲核取代基取代。利用这种与电子给体亲核试剂的反应性，开发了一种合成方法来生产寡苯胺化富勒烯，作为分子内给体-受体A-（D）6具有明确定义的臂数和链长的星爆大分子。HNF与低聚苯胺的反应性随重复苯胺单元数量的增加而增加。在温和条件下与HNF完全反应只需要等摩尔量的四苯胺和十六苯胺即可。在1 H NMR光谱上对材料的质子数进行定量测量，可用于确定低聚苯胺化富勒烯组合物中每C 60的加成数。结果，NMR数据与四苯胺基化和十六烷基苯胺化的富勒烯的结构非常吻合，每个C 60分别含有6个四苯胺基和十六烷基苯胺基臂。DCI也支持HHDAF的这一组成部分–-MS光谱数据显示了碎片化的低聚苯胺基质量离
• Degradable and Electroactive Hydrogels with Tunable Electrical Conductivity and Swelling Behavior
  作者：Baolin Guo、Anna Finne-Wistrand、Ann-Christine Albertsson

  DOI：10.1021/cm103498s

  日期：2011.3.8

  Degradable electrically conducting hydrogels (DECHs), which combine the unique properties of degradable polymers and electrically conducting hydrogels, were synthesized by introducing biodegradable segments into conductive hydrogels. These DECHs were obtained by joining together the photopolymerized macromer acrylated poly(D,L-lactide)-poly(ethylene glycol)-poly(D,L-lactide) (AC-PLA-PEG-PLA-AC), glycidyl methacrylate (GMA), ethylene glycol dimethacrylate (EGDMA) network and aniline tetramer (AT) by the coupling reaction between AT and the GMA The electrical conductivity and swelling behavior of these DECHs were tuned by changing the AT content in the hydrogels, the cross-linking degree, and the environmental pH value. The good electroactivity and thermal stability of these hydrogels were demonstrated by UV-vis spectroscopy, cyclic voltammetry, and TGA tests. The chemical structure and morphology of these polymers were characterized by NMR, FT-IR, SEC, and SEM. These hydrogels possessing both degradability and electrical conductivity represent a new class of biomaterial and will lead to various new possibilities in biomedical applications.
• Morphological and Dimensional Control via Hierarchical Assembly of Doped Oligoaniline Single Crystals
  作者：Yue Wang、Jinglin Liu、Henry D. Tran、Matthew Mecklenburg、Xin N. Guan、Adam Z. Stieg、B. C. Regan、David C. Martin、Richard B. Kaner

  DOI：10.1021/ja301061a

  日期：2012.6.6

  Single crystals of doped aniline oligomers are produced via a simple solution-based self-assembly method. Detailed mechanistic studies reveal that crystals of different morphologies and dimensions can be produced by a "bottom-up" hierarchical assembly where structures such as one-dimensional (1-D) nanofibers can be aggregated into higher order architectures. A large variety of crystalline nanostructures including 1-D nanofibers and nanowires, 2-D nanoribbons and nanosheets, 3-D nanoplates, stacked sheets, nanoflowers, porous networks, hollow spheres, and twisted coils can be obtained by controlling the nucleation of the crystals and the non-covalent interactions between the doped oligomers. These nanoscale crystals exhibit enhanced conductivity compared to their bulk counterparts as well as interesting structure-property relationships such as shape-dependent crystallinity. Furthermore, the morphology and dimension of these structures can be largely rationalized and predicted by monitoring molecule-solvent interactions via absorption studies. Using doped tetraaniline as a model system, the results and strategies presented here provide insight into the general scheme of shape and size control for organic materials.
• Synthesis and spectroscopic properties of aniline tetramers. Comparative studies
  作者：Irena Kulszewicz-Bajer、Izabela Różalska、Małgorzata Kuryłek

  DOI：10.1039/b311096f

  日期：——

  A new synthetic method involving SNAr coupling of 4-fluoronitrobenzene to arylamines, followed by the reduction of the nitro groups, has been developed. Two types of aniline oligomers, namely Ph/NH2 and NH2/NH2 tetramers have been prepared by this method. Tetramers in the leucoemeraldine and in the emeraldine oxidation states were characterized by NMR, UV-Vis-NIR, IR and mass spectroscopies. It shown that the NH2/NH2 tetramer oxidized to the emeraldine state forms two isomers: syn and anti. The oxidation of the Ph/NH2 tetramer leads to the creation of positional isomers, depending on the synthetic method.

  我们开发出了一种新的合成方法，即先将 4-氟硝基苯与芳基胺进行 SNAr 偶联，然后再还原硝基。通过这种方法制备了两种类型的苯胺低聚物，即 Ph/NH2 和 NH2/NH2 四聚物。通过核磁共振、紫外-可见-近红外光谱、红外光谱和质谱分析，对处于白绿宝石氧化态和绿宝石氧化态的四聚体进行了表征。结果表明，氧化成绿宝石态的 NH2/NH2 四聚体会形成两种异构体：同步异构体和反同步异构体。Ph/NH2 四聚体的氧化会产生位置异构体，具体取决于合成方法。