5,11-bis(triisopropylsilylethynyl)anthradithiophene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5,11-bis(triisopropylsilylethynyl)anthradithiophene
• 英文别名: Tri(propan-2-yl)-[2-[12-[2-tri(propan-2-yl)silylethynyl]-6,16-dithiapentacyclo[11.7.0.03,11.05,9.015,19]icosa-1(13),2,4,7,9,11,14,17,19-nonaen-2-yl]ethynyl]silane
• 化学式: C₄₀H₅₀S₂Si₂
• 分子量: 651.14
• InChiKey: JKYYLQCXJNYGGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.56
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,11-bis(triisopropylsilylethynyl)anthradithiophene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到5,11-diethynylanthradithiophene
  参考文献：
  名称：

  Resistance to Unwanted Photo-Oxidation of Multi-Acene Molecules

  摘要：

  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.

  DOI：

  10.1021/acs.joc.0c01890
• 作为产物：
  描述：

  三异丙基硅基乙炔 、 蒽噻吩-5,11-二酮,正反异构体的混合物 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 以60%的产率得到5,11-bis(triisopropylsilylethynyl)anthradithiophene
  参考文献：
  名称：

  Resistance to Unwanted Photo-Oxidation of Multi-Acene Molecules

  摘要：

  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.

  DOI：

  10.1021/acs.joc.0c01890

文献信息

• Stable, Crystalline Acenedithiophenes with up to Seven Linearly Fused Rings
  作者：Marcia M. Payne、Susan A. Odom、Sean R. Parkin、John E. Anthony

  DOI：10.1021/ol048686d

  日期：2004.9.1

  [structure: see text] We report the synthesis of a series of crystalline acenedithiophenes with up to seven linearly fused rings and silylethynyl substituents. These functional groups are designed to both improve solubility and enhance cofacial interactions in the solid. We discuss the crystal packing of these materials, as well as their physical properties such as oxidation potential, UV-vis absorption

  [结构：见正文]我们报告了一系列具有多达七个线性稠合环和甲硅烷基乙炔基取代基的结晶a庚二烯噻吩的合成。这些官能团被设计为既改善溶解度又增强固体中的界面相互作用。我们讨论了这些材料的晶体堆积，以及它们的物理性质，例如氧化电位，UV-vis吸收，荧光发射和分解途径。
• 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.