9-bromo-10-(triisopropylsilylethynyl)anthracene | 880263-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-bromo-10-(triisopropylsilylethynyl)anthracene
• 英文别名: 2-(10-Bromoanthracen-9-yl)ethynyl-tri(propan-2-yl)silane
• CAS: 880263-13-8
• 化学式: C₂₅H₂₉BrSi
• 分子量: 437.495
• InChiKey: IHFSJUWKYRMNJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  497.0±27.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-bromo-10-(triisopropylsilylethynyl)anthracene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.25h， 生成 10-ethynyl-9-[(4-octylphenyl)ethynyl]anthracene
  参考文献：
  名称：

  具有9,10-双(苯基乙炔基)蒽单元的扩展π-共轭化合物的合成与性质

  摘要：

  通过一次性双消除反应和 Sonogashira 偶联合成了具有两个 9,10-双（苯乙炔基）蒽单元和各种接头的新型扩展 π 共轭化合物。他们的紫外线...

  DOI：

  10.1246/bcsj.20140279
• 作为产物：
  描述：

  9,10-二溴蒽 在 正丁基锂 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 、 二氯甲烷 为溶剂， 反应 13.33h， 生成 9-bromo-10-(triisopropylsilylethynyl)anthracene
  参考文献：
  名称：

  New Route to Unsymmetrical 9,10-Disubstituted Ethynylanthracene Derivatives

  摘要：

  描述了含有乙炔基蒽片段的新有机化合物的制备，并给出了选择性合成不对称9,10-二乙炔基蒽的新路径。还报告了一些9-乙炔基-10-取代蒽衍生物的合成。

  DOI：

  10.1055/s-2005-918512

文献信息

• Synthesis of Functionalized Mono-, Bis-, and Trisethynyltriptycenes for One-Dimensional Self-Assembly on Surfaces
  作者：Agnès M. Sirven、Romain Garbage、Yun Qiao、Claire Kammerer、Gwénaël Rapenne

  DOI：10.1002/chem.201502195

  日期：2015.10.12

  This paper describes the synthesis of triptycene‐based building blocks that are able to interact through hydrogen bonds to form one‐dimensional self‐assembled motifs on surfaces. We designed 9,10‐diethynyltriptycene derivatives functionalized at the ethynyl end groups by a variety of hydrogen‐bonding groups for homomolecular recognition and complementary building blocks for heteromolecular recognition

  本文介绍了基于三萜的结构单元的合成，该结构单元能够通过氢键相互作用以在表面上形成一维自组装基序。我们设计了在乙炔基端基上官能化的9,10-二乙炔基三茂基衍生物，该衍生物通过各种氢键基团用于同分子识别，而互补的构建基块则用于异分子识别。我们还介绍了具有末端炔烃官能团的双和三乙炔基三萜烯的合成，这些官能团可用于表面叠氮化物-炔烃环加成反应，以扩大三并烯结构单元的潜力。
• Resistance to Unwanted Photo-Oxidation of Multi-Acene Molecules
  作者：Yu Yan、Zachary A. Lamport、Ioannis Kymissis、Samuel W. Thomas

  DOI：10.1021/acs.joc.0c01890

  日期：2020.10.2

  Although long acenes remain a key class of pi-conjugated molecules for numerous applications, photoinduced oxidation upon exposure of the acene to light, often through sensitization of O-1(2), is an important reaction requiring mitigation for most applications. In response to this ongoing challenge, this paper presents a series of four new diarylethynyl-substituted long acenes-three tetracenes and one anthradithiophene-in which the arylene pendants are either benzene, naphthalene, or anthracene. UV/vis and fluorescence spectroscopy reveals that the anthracene-substituted derivatives fluoresce poorly (Phi < 0.01). Although all four long acenes react with O-1(2) at expected rates when an external photosensitizer is included and show the expected changes in fluorescence to accompany these reactions, the anthracene-substituted derivatives resist direct photoinduced oxidation. Through a combination of mechanistic experiments, we conclude that rapid nonradiative decay of the anthracene-substituted derivatives, perhaps because of inter-arene torsions that emerge in theoretical geometry optimizations, makes these compounds poor photosensitizers for O-1(2) or other reactive oxygen species. This discovery opens new design possibilities for extended acene structures with improved photochemical stability.