1,3,6,8-tetrakis(4-methoxyphenyl)pyrene | 835878-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,3,6,8-tetrakis(4-methoxyphenyl)pyrene
• CAS: 835878-18-7
• 化学式: C₄₄H₃₄O₄
• 分子量: 626.752
• InChiKey: ACQIGBBIIXXECW-UHFFFAOYSA-N

物化性质

• 沸点：
  748.8±60.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3,6,8-tetrakis(4-methoxyphenyl)pyrene 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 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：

  芘 在 四(三苯基膦)钯 、 溴 、 potassium carbonate 作用下， 以 硝基苯 为溶剂， 反应 48.0h， 生成 1,3,6,8-tetrakis(4-methoxyphenyl)pyrene
  参考文献：
  名称：

  1,3,6,8-四芳基py及其阳离子自由基的光物理性质

  摘要：

  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。

  DOI：

  10.1016/j.jphotochem.2019.01.014
• 作为试剂：
  描述：

  3-溴硫代苯甲醚 在 1,3,6,8-tetrakis(4-methoxyphenyl)pyrene 、 氧气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以93 %的产率得到1-bromo-3-methanesulfinyl-benzene
  参考文献：
  名称：

  基于芘的 DA 分子作为高效多相催化剂用于可见光诱导的好氧有机转化

  摘要：

  PhotoCATs：基于芘的供体-受体 (DA) 共轭有机分子被用作高效的多相光催化剂，用于苯甲胺的光催化氧化脱氢偶联、硫醚和芳基硼酸的氧化。这些结构简单的分子可以循环使用多轮，但催化活性会略有下降。大规模（1 mol）苄胺偶联反应在标准条件下顺利进行。

  DOI：

  10.1002/cssc.202202082

文献信息

• Organic light emitting material and organic light emitting device using the same
  申请人：Bin Jong-Kwan

  公开号：US20100164374A1

  公开（公告）日：2010-07-01

  Disclosed is an organic light emitting material having the following chemical formula, for improving luminous efficiency, where R1, R2, R3 and R4 denote materials selected from an aromatic group with 6-24 carbon atoms (C6-C24), the group being independently substituted or unsubstituted, preferably, an aromatic group with 6-24 carbon atoms (C6-C24), the group consisting of trimethylsilane (TMS), CN, halogen (F, Cl, Br) alkyl groups with 1-4 carbon atoms (C1-C4).

  揭示了一种具有以下化学式的有机发光材料，用于提高发光效率，其中R1、R2、R3和R4表示从芳香族群（C6-C24）中选择的材料，该群体可以独立取代或未取代，最好是芳香族群（C6-C24），该群体由三甲基硅烷（TMS）、CN、卤素（F、Cl、Br）和碳原子数为1-4的烷基基团（C1-C4）组成。
• 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)。
• Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes
  作者：Jian-Yong Hu、Xing Feng、Hirotsugu Tomiyasu、Nobuyuki Seto、Ummey Rayhan、Mark R.J. Elsegood、Carl Redshaw、Takehiko Yamato

  DOI：10.1016/j.molstruc.2013.04.074

  日期：2013.9

  Three types of stable pyrene-based highly fluorescence (blue) compounds, 1-, 1,6-bis, 1,8-bis and 1,3,6,8-tetrakis(7-tert-butylpyrenyl)pyrenes and 1,3,6,8-tetrakis[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]pyrene, were successfully synthesized via a Pd/Cu-catalysed Suzuki cross-coupling reaction of the corresponding bromopyrenes with 7-tert-butyl-1-pyrenylboronic ester or 2[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane, respectively. All compounds have good solubility in common organic solvents and high thermal stability with melting points up to 270 degrees C; the exceptions are the isomeric 1,6-bis-, and 1,8-bispyrenyl-substituted pyrenes. All products show high extinction coefficients of absorption (lambda(max)approximate to 349-396 nm) and high quantum yields (lambda(max)approximate to 432-465 nm; Phi(f)approximate to 0.75-0.99) in dichloromethane solution, and emit strong fluorescence in the visible region ranging from deep-blue to pure-blue on increasing the number of substituents. This data suggests that such systems have promise as blue emitters in organic light-emitting device (OLED) applications (OLED = organic light emitting diode). Crystal structures were determined for 1,3,6,8-tetrakis [9,9-bis(3-methylbutyl)-9H-fluoren-2-yl] pyrene and 1,3,6,8-tetrakis(4-methoxyphenyl)pyrene. (C) 2013 Elsevier B.V. All rights reserved.
• 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.
• Blue-Emitting Butterfly-Shaped 1,3,5,9-Tetraarylpyrenes: Synthesis, Crystal Structures, and Photophysical Properties
  作者：Xing Feng、Jian-Yong Hu、Fumitaka Iwanaga、Nobuyuki Seto、Carl Redshaw、Mark R. J. Elsegood、Takehiko Yamato

  DOI：10.1021/ol4002653

  日期：2013.3.15

  The first example of aryl-functionalized, butterfly-shaped, highly fluorescent and stable blue-emitting monomers, namely, 7-tert-butyl-1,3,5,9-tetrakis(p-R-phenyl)pyrenes, were synthesized by the Suzuki-Miyaura cross-coupling reaction from a novel bromide precursor of 1,3,5,9-tetrabromo-7-tert-butylpyrene. The crystal structures and optical and electronic properties have been investigated.