2,6-bis(4-pyridylethynyl)phenol | 951630-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-bis(4-pyridylethynyl)phenol
• 英文别名: 2,6-Bis(2-pyridin-4-ylethynyl)phenol
• CAS: 951630-66-3
• 化学式: C₂₀H₁₂N₂O
• 分子量: 296.328
• InChiKey: QPZYPWKDILAZKA-UHFFFAOYSA-N

物化性质

• 熔点：
  134.4-135.5 °C
• 沸点：
  529.1±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-pyridylethynyl)phenol 、 BOC-L-脯氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.5h， 以61%的产率得到2-(2,6-bis(pyridin-4-ylethynyl)phenyl) 1-(tert-butyl) (S)-pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Endohedral Peptide Lining of a Self-Assembled Molecular Sphere To Generate Chirality-Confined Hollows

  摘要：

  At the interior of a ca. 5 nm-sized self-assembled coordination sphere, 24 amino acids (or peptides) are lined to generate chiralityconfined protein-mimic cavities, whose structures are well-characterized by spectroscopy and X-ray analysis.

  DOI：

  10.1021/ja073629b
• 作为产物：
  描述：

  1-acetoxy-2,6-bis(4-pyridylethynyl)benzene 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以98%的产率得到2,6-bis(4-pyridylethynyl)phenol
  参考文献：
  名称：

  Endohedral Peptide Lining of a Self-Assembled Molecular Sphere To Generate Chirality-Confined Hollows

  摘要：

  At the interior of a ca. 5 nm-sized self-assembled coordination sphere, 24 amino acids (or peptides) are lined to generate chiralityconfined protein-mimic cavities, whose structures are well-characterized by spectroscopy and X-ray analysis.

  DOI：

  10.1021/ja073629b

文献信息

• <i>Endo</i>- and <i>Exo</i>-Functionalized Tetraphenylethylene M₁₂L₂₄ Nanospheres: Fluorescence Emission inside a Confined Space
  作者：Xuzhou Yan、Peifa Wei、Yuhang Liu、Ming Wang、Chuanshuang Chen、Jun Zhao、Guangfeng Li、Manik Lal Saha、Zhixuan Zhou、Zhe An、Xiaopeng Li、Peter J. Stang

  DOI：10.1021/jacs.9b03885

  日期：2019.6.19

  The intrinsic relationship between the properties of green fluorescent protein (GFP) and its encapsulated small molecular light machine has spurred many biomimicking studies, aiming at revealing the detailed mechanism and further promoting its wide applications in different disciplines. However, how to build a similar confined microenvironment to mimic the cavity of a beta-barrel and the fluorescence turn-on process is a fundamental challenge for both chemists and biologists. Herein, two distinct exo- and endo-functionalized tetraphenylethylene (TPE)-based M12L24 nanospheres with precise distribution of anchored TPE moieties and unique photophysical properties were constructed by means of a coordina- tion-driven self-assembly strategy. Under dilute conditions, the nanospheres fluoresce more strongly than the corresponding TPE subcomponents. Meanwhile, the endo-functionalized sphere is able to induce a higher local concentration and more restrained motion of the enclosed 24 TPE units compared with exo-functionalized counterpart and thus induces much stronger emission due to the restriction of the rotation of the pendant TPE units. The biomimetic methodology developed here represents a promising way to understand and construct artificial GFP materials on the platforms of supramolecular coordination complexes.