1,3,6,8-四(4-羟基苯基)芘 | 835878-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 1,3,6,8-四(4-羟基苯基)芘
• 英文名称: 1,3,6,8-tetrakis(4-n-hydroxyphenyl)pyrene
• 英文别名: 1,3,6,8-tetrakis(p-benzoic acid)pyrene；1,3,6,8-tetrakis(4-hydroxyphenyl)pyrene；4,4',4'',4'''-(Pyrene-1,3,6,8-tetrayl)tetraphenol；4-[3,6,8-tris(4-hydroxyphenyl)pyren-1-yl]phenol
• CAS: 835878-20-1
• 化学式: C₄₀H₂₆O₄
• 分子量: 570.644
• InChiKey: QUTBOLCVZGYEJF-UHFFFAOYSA-N

物化性质

• 沸点：
  769.0±55.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1,3,6,8-四(4-羟基苯基)芘 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Solvatochromic Behavior of Pyrene Derivatives with 4-Hydroxyphenyl and 4-Hydroxyphenylethynyl Groups

  摘要：

  1-(4-甲氧基苯基)芘 (PyrPhOMe(1))、1,3,6,8-四(4-甲氧基苯基)芘 (PyrPhOMe(4))、1-(4-甲氧基苯乙炔)芘 (PyrC≡CPhOMe(1))、1,3,6,8-四(4-甲氧基苯乙炔)芘 (PyrC≡CPhOMe(4))、1-(4-羟基苯乙炔)芘 (PyrC≡CPhOH(1)) 和 1,3,6,8-四(4-羟基苯乙炔)芘 (PyrC≡CPhOH(4)) 是通过有机金属复合物催化法合成的。PyrPhOMe(1) 和 PyrPhOMe(4) 的甲氧基去保护是在 BBr3 处理下进行的。通过 NaH 处理 PyrPhOH(1)、PyrPhOH(4)、PyrC≡CPhOH(1) 和 PyrC≡CPhOH(4) 的羟基去质子化引起了吸收和光致发光（PL）峰的红移。去质子化物种的红移随着溶剂的供体数（DN）增加而增加。这些观察可以解释为来自 ONa 基团到芘核心的分子内电荷转移（ICT）的结果。

  DOI：

  10.1246/bcsj.20130144
• 作为产物：
  描述：

  1,3,6,8-四溴芘 在 四(三苯基膦)钯 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 51.0h， 生成 1,3,6,8-四(4-羟基苯基)芘
  参考文献：
  名称：

  Synthesis and Solvatochromic Behavior of Pyrene Derivatives with 4-Hydroxyphenyl and 4-Hydroxyphenylethynyl Groups

  摘要：

  1-(4-甲氧基苯基)芘 (PyrPhOMe(1))、1,3,6,8-四(4-甲氧基苯基)芘 (PyrPhOMe(4))、1-(4-甲氧基苯乙炔)芘 (PyrC≡CPhOMe(1))、1,3,6,8-四(4-甲氧基苯乙炔)芘 (PyrC≡CPhOMe(4))、1-(4-羟基苯乙炔)芘 (PyrC≡CPhOH(1)) 和 1,3,6,8-四(4-羟基苯乙炔)芘 (PyrC≡CPhOH(4)) 是通过有机金属复合物催化法合成的。PyrPhOMe(1) 和 PyrPhOMe(4) 的甲氧基去保护是在 BBr3 处理下进行的。通过 NaH 处理 PyrPhOH(1)、PyrPhOH(4)、PyrC≡CPhOH(1) 和 PyrC≡CPhOH(4) 的羟基去质子化引起了吸收和光致发光（PL）峰的红移。去质子化物种的红移随着溶剂的供体数（DN）增加而增加。这些观察可以解释为来自 ONa 基团到芘核心的分子内电荷转移（ICT）的结果。

  DOI：

  10.1246/bcsj.20130144

文献信息

• Photophysical properties of 1,3,6,8-tetraarylpyrenes and their cation radicals
  作者：Vijay S. Vyas、Sergey V. Lindeman、Rajendra Rathore

  DOI：10.1016/j.jphotochem.2019.01.014

  日期：2019.4

  groups and the pyrene core. Electronic absroption spectra of the cation radicals generated in solution by the single electron oxidation of pyrenes reaffirmed the coupling of the aryl rings with the pyrene. The aryl groups at 1,3,6,8-positions completely inhibit the π-stacking of pyrene core in solution. Crystal structure of the cation radical salt of tetraphenyl shows charge delocalization between neutral

  描述了1,3,6,8-四芳基取代的pyr的合成。芳基上的取代基影响the核的光电性质，表明芳基和the核之间的强耦合。通过solution的单电子氧化在溶液中产生的阳离子自由基的电子吸收光谱证实了芳基环与the的偶联。1,3,6,8-位的芳基完全抑制溶液中of核的π堆积。四苯基阳离子自由基盐的晶体结构显示中性pyr单元和两个阳离子pyr核之间的电荷离域。当树枝状五苯基围绕surround核时，在阳离子自由基的固态下观察到核堆积的完全抑制。
• Robust and Dynamic Polymer Networks Enabled by Woven Crosslinks
  作者：Guangfeng Li、Jun Zhao、Zhaoming Zhang、Xinyang Zhao、Lin Cheng、Yuhang Liu、Zhewen Guo、Wei Yu、Xuzhou Yan

  DOI：10.1002/anie.202210078

  日期：2022.10.24

  Woven nodes, serving as dynamic crosslinks, afford a woven polymer network (WPN). The WPN exhibits comparable stiffness, strength, elastic recovery, and anti-fatigue properties to those of covalent polymer networks (CPN), but also possesses decent mechanical adaptivity, self-healing, and reprocessability, resembling those of supramolecular polymer networks (SPN).

  用作动态交联的编织节点提供编织聚合物网络 (WPN)。WPN 表现出与共价聚合物网络 (CPN) 相当的刚度、强度、弹性恢复和抗疲劳性能，但也具有良好的机械适应性、自愈性和可再加工性，类似于超分子聚合物网络 (SPN)。
• Tetraphenylpyrene-Bridged Periodic Mesostructured Organosilica Films with Efficient Visible-Light Emission
  作者：Norihiro Mizoshita、Yasutomo Goto、Yoshifumi Maegawa、Takao Tani、Shinji Inagaki

  DOI：10.1021/cm9034787

  日期：2010.4.27

  Mesostructured organosilica films with strong blue fluorescence emission were synthesized by surfactant-templated sol-gel polycondensation using a 1,3,6,8-tetraphenylpyrene (TPPy)-containing organosilane precursor. The TPPy precursor, which contained four polymerizable silyl groups, was suitable for the preparation of mesostructured films with high TPPy content in the framework. The fluorescence quantum yields of the TPPy-bridged mesostructured organosilica films reached more than 0.7, despite the dense accumulation of TPPy units within the framework. Doping of the mesostructured films with fluorescence dyes enabled fine-tuning of the emission colors over a wide range of the visible spectrum Such mesostructured organosilica films, in which different chromophores can be distributed into the framework and mesopores, have significant potential for luminescence applications
• Independent Quantification of Electron and Ion Diffusion in Metallocene-Doped Metal–Organic Frameworks Thin Films
  作者：Paula J. Celis-Salazar、Meng Cai、Clark A. Cucinell、Spencer R. Ahrenholtz、Charity C. Epley、Pavel M. Usov、Amanda J. Morris

  DOI：10.1021/jacs.9b03609

  日期：2019.7.31

  The chronoamperometric response (I vs t) of three metallocene-doped metal-organic frameworks (MOFs) thin films (M-NU-1000, M = Fe, Ru, Os) in two different electrolytes (tetrabutylammonium hexafluorophosphate [TBAPF(6)] and tetrabutylammonium tetrakis(pentafluorophenyl)borate [TBATFAB]) was utilized to elucidate the diffusion coefficients of electrons and ions (D-e and D-i, respectively) through the structure in response to an oxidizing applied bias. The application of a theoretical model for solid state voltammetry to the experimental data revealed that the diffusion of ions is the rate determining step at the three different time stages of the electrochemical transformation: an initial stage characterized by rapid electron diffusion along the crystal-solution boundary (stage A), a second stage that represents the diffusion of electrons and ions into the bulk of the MOF crystallite (stage B), and a final period of the conversion dominated only by the diffusion of ions (stage C). Remarkably, electron diffusion (D-e) increased in the order of Fe < Ru < Os using PF61- as the counteranion in all the stages of the voltammogram, demonstrating the strategy to modulate the rate of electron transport through the incorporation of rapidly self-exchanging molecular moieties into the MOF structure. The D-e values obtained with larger TFAB(1-) counteranion were generally in agreement with the previous trend but were on average lower than those obtained with PF61-. Similarly, the ion diffusion coefficient (D-i()) was generally higher for TFAB(1-) than for PF61- as the ions diffuse into the crystal bulk, due to the high degree of ion-pair association between PF61- and the metallocenium ion, resulting in a faster penetration of the weakly associated TFAB(1-) anion through the MOF pores. These structure-function relationships provide a foundation for the future design, control, and optimization of electron and ion transport properties in MOF thin films.