5,12-双（（三异丙基甲硅烷基）乙炔基）并四苯 | 628316-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 中文名称: 5,12-双（（三异丙基甲硅烷基）乙炔基）并四苯
• 英文名称: 5,12-bis((triisopropylsilyl)ethynyl)tetracene
• 英文别名: tri(propan-2-yl)-[2-[12-[2-tri(propan-2-yl)silylethynyl]tetracen-5-yl]ethynyl]silane
• CAS: 628316-50-7
• 化学式: C₄₀H₅₂Si₂
• 分子量: 589.024
• InChiKey: CHIWZTMMQIHUNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.29
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  5,12-双（（三异丙基甲硅烷基）乙炔基）并四苯 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 生成 5,12-diethynyltetracene
  参考文献：
  名称：

  Gold(I) and Platinum(II) Tetracenes and Tetracenyldiacetylides: Structural and Fluorescence Color Changes Induced by σ-Metalation

  摘要：

  sigma-Metalation of tetracene can change the emission color of and introduce new structural dimensionality to the organic chromophore. Two synthetic entries to sigma-metallotetracenes have been explored, leading to emissive mononuclear (Ph3PAuI)-tetracene (1) and cis-[Br(Et3P)(2)Pt-II]-tetracene (2) and binuclear (R3PAu(I))(2)-tetracenyldiacetylide (R = Ph (4), Me (5)) and trans-[I(Et3P)(2)Pt-II](2)-tetracenyldiacetylide (6). Metalation can lower the emission energy of tetracene up to 0.53 eV. The X(Et3P)(2)Pt-II group (X = Br, I) has stronger perturbations on the tetracenyl ring than the R3PAu(I) group. sigma-Metalation also leads to different crystal packing of the complexes and thus arrangements of the tetracenyl rings. Aurophilic attraction operates in 5, leading to self-assembly of the molecules into a novel honeycomb structure composed of helical Au-I chains. In contrast to the other complexes, the crystal of 5 is not emissive, possibly due to efficient exciton delocalization.

  DOI：

  10.1021/om100046h
• 作为产物：
  描述：

  四溴对烯 在 正丁基锂 、 calcium carbonate 、 sodium iodide 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 5,12-双（（三异丙基甲硅烷基）乙炔基）并四苯
  参考文献：
  名称：

  Tetracene Derivatives as Potential Red Emitters for Organic LEDs

  摘要：

  As part of our program investigating the use of ethynylated acenes in organic electronics, we have prepared a series of functionalized tetracene derivatives in search of a material with red emission suitable for use in display technologies. A number of such compounds with functionalization on the alkyne and/or the acene ring were easily prepared in one or two steps from commercially available materials. Solution fluorescence quantum efficiencies were generally good for these derivatives, which possessed emission maxima spanning the range 540-637 nm. Simple light-emitting diodes fabricated from these compounds showed that one of the derivatives did exhibit red electroluminescence.

  DOI：

  10.1021/ol035415e

文献信息

• Why Triple Bonds Protect Acenes from Oxidation and Decomposition
  作者：Werner Fudickar、Torsten Linker

  DOI：10.1021/ja306056x

  日期：2012.9.12

  Furthermore, the products obtained from thermolysis and the kinetics of the thermolysis are investigated. Density functional theory is applied in order to predict reaction energies, frontier molecular orbital interactions, and radical stabilization energies. The combined results allow us to describe the mechanisms of the oxidations and the subsequent thermolysis. We found that the alkynyl group not only

  介绍了官能团对高级并苯氧化稳定性影响的实验和计算研究。我们合成了在外围具有各种取代基的蒽、并四苯和并五苯，鉴定了它们的光氧化产物，并测量了动力学。此外，研究了从热解获得的产物和热解的动力学。应用密度泛函理论来预测反应能、前沿分子轨道相互作用和自由基稳定能。综合结果使我们能够描述氧化和随后的热解的机制。我们发现炔基不仅可以增强并苯的氧化稳定性，还可以保护所得内过氧化物免受热分解。此外，这种取代基增加并四苯和并五苯光氧化的区域选择性。第一次，我们通过使用化学生成的单线态氧 ((1)O(2)) 氧化炔基并五苯，无需辐照，并确定 6,13-​​endoperoxide 作为唯一的区域异构体。这种氧化的双分子速率常数仅为 1 × 10(5) s(-1) M(-1)。这种出乎意料的缓慢反应是 (1)O(2) 物理失活的结果。与未取代或芳基取代的并苯相比，炔基取代的并苯的光氧化作用最有可能通过协同机制进
• Sequence-Specific Synthesis of Platinum-Conjugated Trichromophoric Energy Cascades of Anthracene, Tetracene, and Pentacene and Fluorescent “Black Chromophores”
  作者：Minh-Hai Nguyen、Van Ha Nguyen、John H. K. Yip

  DOI：10.1021/om400578t

  日期：2013.12.23

  A sequence-specific synthesis of trichromophoric energy cascades containing anthracenyl (A), tetracenyl (T), or pentacenyl (P) rings is achieved by coupling PtII ions and singly desilylated bis(triisopropylsilylethynyl)acenes (acene = anthracene, tetracene, or pentacene). Four sequences, T-P-T, P-T-P, A-P-T, and A-T-P, are generated. Absorption spectra of the triads show intense bands due to the S0

  含有蒽（三发色能量级联的序列特异性合成甲），并四（Ť），或并五苯基（P）环通过连接的PT实现II离子和单脱甲硅烷基双（三异丙）并苯（并苯=蒽，并四苯，或并五苯）。四个序列，TPT，PTP，APT，和ATP，生成。的三单元组的吸收光谱显示强条带由于在S 0 →S 1的并苯的过渡。该APT和ATP能够在整个可见光区域强烈吸收的“黑色生色团”是罕见的例子。示出了不同的序列具有不同的发射指纹。的发射光谱APT和ATP表明激发在S 0 →S 1个的带甲引起排放量从S 1的激发态甲，Ť，和P，从激发态意味着能量转移的存在阿到T和P的那些。
• Structure, photophysics, and photooxidation of crowded diethynyltetracenes
  作者：Jingjing Zhang、Syena Sarrafpour、Terry E. Haas、Peter Müller、Samuel W. Thomas

  DOI：10.1039/c2jm16173g

  日期：——

  This paper describes a previously unreported class of sterically crowded tetracene derivatives that have both phenyl and ethynyl substituents. The steric crowding above and below the tetracene core prevents overlap between the extended π-systems of the acenes. Substituent effects cause these tetra-substituted tetracenes to have absorbance and fluorescence spectra red shifted from either disubstituted derivatives or rubrenes, such that they have spectra similar to diarylpentacenes, but with higher quantum yields of fluorescence and greater photostability. These new molecules also undergo cycloaddition reactions with 1O2, giving regioisomeric mixtures of endoperoxides, and in contrast to longer acenes, the ethynyl substituents show only a modest stabilizing effect to photooxidation. Ethynylated tetracenes also exhibited photochromism, with their endoperoxides undergoing cycloreversion to yield the acene starting material at room temperature in the dark.

  本文描述了一类先前未报道的空间拥挤并四苯衍生物，它们同时具有苯基和乙炔基取代基。并四苯核心上方和下方的空间拥挤防止了并苯的扩展 π 系统之间的重叠。取代效应导致这些四取代并四苯的吸光度和荧光光谱从二取代衍生物或红荧烯红移，使得它们具有与二芳基并五苯相似的光谱，但具有更高的荧光量子产率和更高的光稳定性。这些新分子还与 1O2 发生环加成反应，产生内过氧化物的区域异构混合物，并且与较长的并苯相比，乙炔基取代基仅对光氧化表现出适度的稳定作用。乙炔化并四苯也表现出光致变色性，其内过氧化物在室温下在黑暗中发生环化反应以产生并苯起始材料。
• Single‐Photon Near‐Infrared‐Responsiveness from the Molecular to the Supramolecular Level via Platination of Pentacenes
  作者：Yifei Han、Yueru Yin、Fan Wang、Feng Wang

  DOI：10.1002/anie.202103125

  日期：2021.6.14

  σ-platinated pentacenes facilitates NIR responsiveness in one-dimensional supramolecular polymers, resulting in the disappearance of supramolecular chirality signals and disruption of self-assembled nanofibers. Overall, the σ-platination strategy opens up new avenues toward NIR photo-responsive materials at the molecular and supramolecular levels.

  近红外 (NIR) 响应对各种应用都很重要。目前，与显示双光子吸收和三重态-三重态湮灭过程的系统相比，单光子 NIR 响应系统很少见。由于空间限制效应，光响应发色团的超分子堆叠导致效率降低。在此，我们表明并五苯的 σ 铂化是构建单光子 NIR 响应系统的可行方案，其优点包括低 HOMO-LUMO 能隙、高光化学效率和通路特异性。并五苯到内过氧化的转变伴随着颜色和吸光度的变化。σ-镀并并五苯的高光氧化效率促进了一维超分子聚合物的近红外响应，导致超分子手性信号的消失和自组装纳米纤维的破坏。总的来说，σ-铂化策略为分子和超分子水平的近红外光响应材料开辟了新的途径。