2,6-bis(methylthio)-3,7-bis(trimethylsilylethynyl)anthracene | 1397972-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6-bis(methylthio)-3,7-bis(trimethylsilylethynyl)anthracene
• 英文别名: 2,6-bis(trimethylsilylethynyl)-3,7-bis(methylthio)anthracene；2-[3,7-Bis(methylsulfanyl)-6-(2-trimethylsilylethynyl)anthracen-2-yl]ethynyl-trimethylsilane；2-[3,7-bis(methylsulfanyl)-6-(2-trimethylsilylethynyl)anthracen-2-yl]ethynyl-trimethylsilane
• CAS: 1397972-24-5
• 化学式: C₂₆H₃₀S₂Si₂
• 分子量: 462.827
• InChiKey: ITFCJESPPZSLQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.89
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-bis(methylthio)-3,7-bis(trimethylsilylethynyl)anthracene 在 四(三苯基膦)钯 、 tripotassium phosphate "n" hydrate 、 碘 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3,9-diphenylanthra[2,3-b:6,7-b']dithiophene
  参考文献：
  名称：

  Isomerically Pure Anthra[2,3-b:6,7-b′]-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

  摘要：

  A new straightforward synthesis of isomerically pure anthra[2,3-b:6,7-b'] -difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS) from readily available 2,6-dimethoxyanthracene is described. The present successful synthesis makes it possible to overview the linear-shaped anti-acenedichalcogenophene compounds, that is, benzo[1,2-b:4,5-b']-, naphtho[2,3-b:6,7-b']-, and anthra[2,3-b:6,7-b']- difuran, -dithiophene, and -diselenophene. By comparing their electrochemical and photochemical properties, the electronic structures of acenedichalcogenophenes can be expressed as the outcome of balance between the central acene core and the outermost chalcogenophene rings. Among isomerically pure parent anti-anthradichalcogenophenes, anti-ADT and anti-ADS can afford crystalline thin films by vapor deposition, which acted as active layer in organic field-effect transistors with mobility as high as 0.3 cm(2) V-1 s(-1) for ADT and 0.7 cm(2) V-1 s(-1) for ADS. The mobility of isomerically pure anti-ADT is higher by several times than those reported for isomercally mixed ADT, implying that the isomeric purity could be beneficial for realizing the better FET mobility. We also tested the diphenyl derivatives of anti-ADF, -ADT, and -ADS as the active material for OFET devices, which showed high mobility of up to 1.3 cm(2) V-1 s(-1).

  DOI：

  10.1021/jo301438t
• 作为产物：
  描述：

  3,7-bis(methylthio)anthracene-2,6-diol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 2,6-bis(methylthio)-3,7-bis(trimethylsilylethynyl)anthracene
  参考文献：
  名称：

  Isomerically Pure Anthra[2,3-b:6,7-b′]-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors

  摘要：

  A new straightforward synthesis of isomerically pure anthra[2,3-b:6,7-b'] -difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS) from readily available 2,6-dimethoxyanthracene is described. The present successful synthesis makes it possible to overview the linear-shaped anti-acenedichalcogenophene compounds, that is, benzo[1,2-b:4,5-b']-, naphtho[2,3-b:6,7-b']-, and anthra[2,3-b:6,7-b']- difuran, -dithiophene, and -diselenophene. By comparing their electrochemical and photochemical properties, the electronic structures of acenedichalcogenophenes can be expressed as the outcome of balance between the central acene core and the outermost chalcogenophene rings. Among isomerically pure parent anti-anthradichalcogenophenes, anti-ADT and anti-ADS can afford crystalline thin films by vapor deposition, which acted as active layer in organic field-effect transistors with mobility as high as 0.3 cm(2) V-1 s(-1) for ADT and 0.7 cm(2) V-1 s(-1) for ADS. The mobility of isomerically pure anti-ADT is higher by several times than those reported for isomercally mixed ADT, implying that the isomeric purity could be beneficial for realizing the better FET mobility. We also tested the diphenyl derivatives of anti-ADF, -ADT, and -ADS as the active material for OFET devices, which showed high mobility of up to 1.3 cm(2) V-1 s(-1).

  DOI：

  10.1021/jo301438t

文献信息

• “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
  作者：Chengyuan Wang、Daisuke Hashizume、Masahiro Nakano、Takuya Ogaki、Hiroyuki Takenaka、Kohsuke Kawabata、Kazuo Takimiya

  DOI：10.1039/c9sc05902d

  日期：——

  structures of organic semiconductors in the solid state play critical roles in determining the performances of their optoelectronic devices, such as organic field-effect transistors (OFETs). It is a formidable challenge to rationally design molecular packing in the solid state owing to the difficulty of controlling intermolecular interactions. Here we report a unique materials design strategy based

  固态有机半导体的堆积结构在确定其光电器件（例如有机场效应晶体管（OFET））的性能方面起着至关重要的作用。由于难以控制分子间的相互作用，合理设计固态的分子堆积是一个巨大的挑战。在这里，我们报告了一种独特的材料设计策略，该策略基于a庚二噻吩的β-甲基硫磺化来一般性地和选择性地控制材料的堆积结构，以创造出可与红rival烯竞争的有机半导体，而红rub烯是一种在固体中具有特征性的π堆积结构的基准高迁移率材料州。此外，通过Hirshfeld表面分析以及基于对称自适应扰动理论（SAPT）的理论计算，分析了β-甲基硫磺化对堆积结构的影响。结果清楚地表明，cen苯并噻吩的β-甲硫基化可以通过破坏亲本cen苯并噻吩的有利的边对面方式并同时诱导β-苯并噻吩的面对面和端面相互作用来普遍改变分子间的相互作用。甲基亚硫酰a二噻吩。这种操纵分子间相互作用的“破坏和诱导”策略可以为基于分子结构的合理包装设计打开一扇门