1-(trimethylsilylethynyl)pyrene | 253271-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-(trimethylsilylethynyl)pyrene
• 英文别名: trimethyl(pyren-1-ylethynyl)silane；trimethyl(2-pyren-1-ylethynyl)silane
• CAS: 253271-87-3
• 化学式: C₂₁H₁₈Si
• 分子量: 298.459
• InChiKey: SKFFHUMDLPRRLR-UHFFFAOYSA-N

物化性质

• 沸点：
  422.9±18.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  应存放在室温、避光且惰性气体保护的环境中。

反应信息

• 作为反应物：
  描述：

  1-(trimethylsilylethynyl)pyrene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到1-乙炔基芘
  参考文献：
  名称：

  苯并二呋喃官能化的and和蒽荧光团的合成，结构，氧化还原和光物理性质†

  摘要：

  苯并呋喃官能化 芘 和 蒽以合理的产率获得了荧光团1和2。已经描述了它们的单晶结构，电化学，光吸收和荧光特性。他们表现出与0.53高量子产率强荧光1和0.48 2。

  DOI：

  10.1039/c1ob05778b
• 作为产物：
  描述：

  芘 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溶剂黄146 、 三乙胺 、 benzyltrimethylazanium tribroman-2-uide 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 1-(trimethylsilylethynyl)pyrene
  参考文献：
  名称：

  Tunable star-shaped triphenylamine fluorophores for fluorescence quenching detection and identification of nitro-aromatic explosives

  摘要：

  含有芘或芫荽烯的三苯胺基荧光团对硝基炸药显示出不同的荧光淬灭灵敏度。最灵敏的荧光团能够检测到 ng cm-2 级的 TNT；该阵列可用于识别硝基芳烃。

  DOI：

  10.1039/c2cc34008a

文献信息

• Copper-Mediated Deacylative Coupling of Ynones via C–C Bond Activation under Mild Conditions
  作者：Lili Feng、Tingjun Hu、Saisai Zhang、Heng-Ying Xiong、Guangwu Zhang

  DOI：10.1021/acs.orglett.9b03684

  日期：2019.12.6

  The intermolecular deacylative coupling of unstrained ynones via C-C bond activation was accomplished by a CuCl-bpy system under mild reaction conditions. This protocol features facile cleavage of the C-C bond at room temperature, broad substrate scope, and efficient construction of important symmetric and unsymmetrical 1,3-diyne adducts through homo or cross coupling of ynones, respectively. The preliminary

  通过温和的反应条件下的CuCl-bpy系统完成了未应变的炔酮通过CC键活化的分子间脱酰基反应。该协议的特点是在室温下容易裂解CC键，广泛的底物范围，以及通过炔酮的均相或交联分别有效构建重要的对称和不对称1,3-二炔加合物的方法。初步的机械研究表明，此过程可能涉及酰基铜（III）配合物。
• Templated Chromophore Assembly by Dynamic Covalent Bonds
  作者：Lou Rocard、Andrey Berezin、Federica De Leo、Davide Bonifazi

  DOI：10.1002/anie.201507186

  日期：2015.12.21

  Through the simultaneous use of three orthogonal dynamic covalent reactions, namely disulfide, boronate, and acyl hydrazone formation, we conceived a facile and versatile protocol to spatially organize tailored chromophores, which absorb in the blue, red, and yellow regions, on a preprogrammed α‐helix peptide. This approach allowed the assembly of the dyes in the desired ratio and spacing, as dictated

  通过同时使用三个正交的动态共价反应，即二硫键，硼酸酯和酰基的形成，我们构想了一种灵活而通用的方案，可在空间上组织定制的生色团，该生色团在预先编程的α上吸收蓝色，红色和黄色区域螺旋肽 该方法允许染料以所需的比率和间距组装，这由识别单元在肽支架上的相对位置和分布所决定。稳态UV / Vis吸收和发射研究表明，能量从黄色和红色供体转移到蓝色受体。分子动力学模拟支持实验结果，即组装后螺旋结构得以保持，并且三种染料被限制在定义的构象空间中。
• Synthesis of star-shaped molecules with pyrene-containing π-conjugated units linked by an organosilicon core
  作者：Joji Ohshita、Yosuke Hatanaka、Shigenori Matsui、Yousuke Ooyama、Yutaka Harima、Yoshihito Kunugi

  DOI：10.1002/aoc.1551

  日期：——

  Star‐shaped molecules with pyrene‐containing π‐conjugated units linked by an organosilicon core (Py3Si and Py3C) were prepared and their applications to thin‐film transistors (TFTs) and photovoltaic cells were studied. Bottom‐contact type TFTs with spin‐coated films of the star‐shaped compounds as the active layers were prepared and the field‐effect mobility (µFET) and Ion/Ioff ratios were determined

  制备了带有molecules键的π共轭单元的星形分子，这些分子通过有机硅核（Py 3 Si和Py 3 C）连接，并研究了它们在薄膜晶体管（TFTs）和光伏电池中的应用。制备了以星形化合物的旋涂膜作为有源层的底接触型TFT，其场效应迁移率（µ FET）和I on / I off比确定为大约10 -5 cm 2 V -1 s -1和10 4。Py 3 Si和Py 3的光伏特性在ITO–PEDOT–PSS–Py 3 Si或Py 3 C–PCBM–LiF–Al细胞中研究了碳。尽管电池的功率转换效率（PCE）仅为约0.04％，但它们显示出0.8-0.9 V的高开路电压（V oc），表明此类化合物作为基质材料具有很高的潜力。版权所有©2009 John Wiley＆Sons，Ltd.
• A novel pyrene-containing fluorescent organogel derived from a quinoline-based fluorescent porbe: synthesis, sensing properties, and its aggregation behavior
  作者：Chang-Bo Huang、Li-Jun Chen、Junhai Huang、Lin Xu

  DOI：10.1039/c4ra02373k

  日期：——

  A new family of pyrene-containing compounds 2–4 derived from aminoquinoline-containing fluorescent probe 1 were successfully synthesized and well characterized. The investigation of the absorption and emission spectra of these compounds revealed that the photophysical properties were significantly affected by the substitution of pyrene. Moreover, these compounds exhibited selective fluorescence behaviour towards Zn2+ in aqueous solution. The gelation properties of these compounds were investigated by the “stable to inversion of a test tube” method. Interestingly, 1,8-bis-substituted compound 4 displayed stable gel-formation properties in acetone, dioxane, tetrahydrofuran, ethyl acetate, chloroform, and dichloromethane. The morphologies of the xerogels were investigated by scanning electron microscopy (SEM) and laser scanning confocal microscopy (LSCM). The concentration- and temperature-dependent emission properties, and concentration- and temperature-variable 1H NMR spectroscopy of compound 4 were investigated, which suggested that both π–π stacking interaction and hydrogen bonding were the driving forces for the process of self-aggregation and the gel formation. In addition, studies on the luminescence properties indicated that 4 had the ability to form a fluorescent organogel with interesting fluorescence behaviour. More importantly, it was found that compound 4 could form a stimuli-responsive gel that had a sensitive gel-to-sol transition response to heating or adding Zn2+.

  从含氨基喹啉的荧光探针1成功合成并表征了一类新的含芘化合物2-4。对这些化合物的吸收和发射光谱的研究表明，光物理性质显著受到芘取代的影响。此外，这些化合物在水溶液中对Zn2+展示了选择性的荧光行为。通过“测试管稳定反转”方法研究了这些化合物的凝胶化性质。有趣的是，1,8-双取代化合物4在丙酮、二氧六环、四氢呋喃、乙酸乙酯、氯仿和二氯甲烷中表现出稳定的凝胶形成性质。通过扫描电子显微镜（SEM）和激光扫描共聚焦显微镜（LSCM）研究了凝胶的形态。研究了化合物4的浓度依赖性和温度依赖性的发射性质，以及浓度和温度可变的1H NMR光谱，结果表明π–π堆积相互作用和氢键是自聚集和凝胶形成过程的驱动力。此外，对发光性质的研究表明，4具有形成具有有趣荧光行为的荧光有机凝胶的能力。更重要的是，发现化合物4能够形成刺激响应性凝胶，对加热或添加Zn2+具有敏感的凝胶-溶胶转变响应。
• Aerobic Oxynitration of Alkynes with ^<i>t</i>BuONO and TEMPO
  作者：Uttam Dutta、Soham Maity、Rajesh Kancherla、Debabrata Maiti

  DOI：10.1021/ol503025n

  日期：2014.12.19

  An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

  已经报道了炔的立体选择性硝基氨基羟化的有效方法。该反应具有广泛的底物范围，良好的官能团耐受性和高产率。合成有用的α-硝基酮可以一步一步地通过这些产品获得。