3,9-diiodo-2,8-bis(trimethylsilyl)anthra[2,3-b:6,7-b']-dithiophene | 1397972-26-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3,9-diiodo-2,8-bis(trimethylsilyl)anthra[2,3-b:6,7-b']-dithiophene
• 英文别名: Adt-tmsi；(8,18-diiodo-17-trimethylsilyl-6,16-dithiapentacyclo[11.7.0.03,11.05,9.015,19]icosa-1(20),2,4,7,9,11,13,15(19),17-nonaen-7-yl)-trimethylsilane
• CAS: 1397972-26-7
• 化学式: C₂₄H₂₄I₂S₂Si₂
• 分子量: 686.567
• InChiKey: APZVQRIZIMPEKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.72
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3,9-diiodo-2,8-bis(trimethylsilyl)anthra[2,3-b:6,7-b']-dithiophene 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 蒽[2,3-b：6,7-b']二噻吩
  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：

  2,6-bis(methylthio)-3,7-bis(trimethylsilylethynyl)anthracene 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,9-diiodo-2,8-bis(trimethylsilyl)anthra[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