1,30-Bis-[tris(3,5-di-tert-butylphenyl)]triaconta-2,4,6,8,10,12,14,16,18,20,22,24,26,28-tetradecayne | 1257847-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,30-Bis-[tris(3,5-di-tert-butylphenyl)]triaconta-2,4,6,8,10,12,14,16,18,20,22,24,26,28-tetradecayne
• 英文别名: 1,3-ditert-butyl-5-[1,1,30,30,30-pentakis(3,5-ditert-butylphenyl)triaconta-2,4,6,8,10,12,14,16,18,20,22,24,26,28-tetradecaynyl]benzene
• CAS: 1257847-32-7
• 化学式: C₁₁₄H₁₂₆
• 分子量: 1496.25
• InChiKey: MMAPXBRGPIPRLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  36
• 重原子数：
  114
• 可旋转键数：
  33
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以7.3%的产率得到1,30-Bis-[tris(3,5-di-tert-butylphenyl)]triaconta-2,4,6,8,10,12,14,16,18,20,22,24,26,28-tetradecayne
  参考文献：
  名称：

  聚炔 [3] 轮烷：通过羰基二钴配合物合成并增强稳定性

  摘要：

  羰基钴配合物已被用作临时掩蔽基团和临时终止剂，用于合成具有两个大环在 C 28螺纹上的聚炔 [3] 轮烷。比较具有不同螺纹大环的两种[3]轮烷的热稳定性表明，2,6-吡啶基环对苯撑纳米环有效地稳定了聚炔链。

  DOI：

  10.1002/anie.202116897

文献信息

• Synthesis of polyynes to model the sp-carbon allotrope carbyne
  作者：Wesley A. Chalifoux、Rik R. Tykwinski

  DOI：10.1038/nchem.828

  日期：2010.11

  Carbyne is an allotrope of carbon composed of sp-hybridized carbon atoms. Although its formation in the laboratory is suggested, no well-defined sample is described. Interest in carbyne and its potential properties remains intense because of, at least in part, technological breakthroughs offered by other carbon allotropes, such as fullerenes, carbon nanotubes and graphene. Here, we describe the synthesis of a series of conjugated polyynes as models for carbyne. The longest of the series consists of 44 contiguous acetylenic carbons, and it maintains a framework clearly composed of alternating single and triple bonds. Spectroscopic analyses for these polyynes reveal a distinct trend towards a finite gap between the highest occupied molecular orbital and the lowest unoccupied molecular orbital for carbyne, which is estimated to be ∼485 nm (∼2.56 eV). Even the longest members of this series of polyynes are not particularly sensitive to light, moisture or oxygen, and they can be handled and characterized under normal laboratory conditions. The structure of the carbon allotrope ‘carbyne’ is based on a framework of sp-hybridized carbon. To model its properties, a series of conjugated polyynes — the longest of which contains 44 contiguous acetylenic carbons — have been synthesized and their spectroscopic properties investigated.

  碳炔是由sp杂化碳原子组成的碳同素异形体。虽然有人提出在实验室中可以合成碳炔，但尚未有明确的样品描述。人们对碳炔及其潜在特性的兴趣仍然浓厚，至少部分原因是其他碳同素异形体（如富勒烯、碳纳米管和石墨烯）带来了技术突破。在此，我们描述了一系列共轭聚炔的合成，作为碳炔的模型。该系列中最长的由44个连续的乙炔碳组成，其结构明显由交替的单键和三键组成。对这些聚炔的光谱分析表明，碳炔的最高被占分子轨道和最低未占分子轨道之间存在一个有限的间隙，估计为≦485 nm（≦2.56 eV）。即使该系列聚炔中最长的成员对光、湿气或氧气也不特别敏感，它们可以在正常的实验室条件下进行操作和表征。碳同素异形体“碳炔”的结构基于sp杂化碳的框架。为了模拟其特性，我们合成了一系列共轭聚炔（其中最长的一组包含44个连续的乙炔碳），并研究了它们的光谱特性。
• Masked alkynes for synthesis of threaded carbon chains
  作者：Connor W. Patrick、Yueze Gao、Prakhar Gupta、Amber L. Thompson、Anthony W. Parker、Harry L. Anderson

  DOI：10.1038/s41557-023-01374-z

  日期：2024.2

  many threaded macrocycles have been synthetically inaccessible. Here we show that masked alkynes, in which the C≡C triple bond is temporarily coordinated to cobalt, can be used to synthesize polyrotaxanes, up to the C68 [5]rotaxane with 34 contiguous triple bonds and four threaded macrocycles. This is the length regime at which the electronic properties of polyynes converge to those of carbyne. Cyclocarbons

  多炔是具有交替单键和三键的sp 1碳原子链。随着它们变得更长，它们会演化为碳炔（碳的一维同素异形体），并且变得越来越不稳定。人们预计长多炔可以通过超分子封装来稳定，通过将它们穿过大环形成聚轮烷，但是到目前为止，具有许多螺纹大环的多炔聚轮烷在合成上是无法获得的。在这里，我们证明了掩蔽炔烃（其中C=C三键暂时与钴配位）可用于合成聚轮烷，直至具有34个连续三键和四个螺纹大环的C 68 [5]轮烷。这是多炔的电子性质收敛于碳炔的电子性质的长度范围。环碳构成分子碳同素异形体的相关家族，钴掩蔽的炔烃也提供了分别围绕环[40]碳和环[80]碳的钴配合物构建的[3]环烷和[5]环烷的路线。
• Polyyne [3]Rotaxanes: Synthesis via Dicobalt Carbonyl Complexes and Enhanced Stability
  作者：Connor W. Patrick、Joseph F. Woods、Przemyslaw Gawel、Claire E. Otteson、Amber L. Thompson、Tim D. W. Claridge、Ramesh Jasti、Harry L. Anderson

  DOI：10.1002/anie.202116897

  日期：2022.3

  Cobalt carbonyl complexes have been used as temporary masking group, and temporary stoppers, in the synthesis of polyyne [3]rotaxanes with two macrocycles threaded on a C28 thread. Comparison of the thermal stability of two [3]rotaxanes with different threaded macrocycles shows that the 2,6-pyridyl cycloparaphenylene nanohoop effectively stabilizes the polyyne chain.

  羰基钴配合物已被用作临时掩蔽基团和临时终止剂，用于合成具有两个大环在 C 28螺纹上的聚炔 [3] 轮烷。比较具有不同螺纹大环的两种[3]轮烷的热稳定性表明，2,6-吡啶基环对苯撑纳米环有效地稳定了聚炔链。