anthra[2,3-b:6,7-b']difuran | 1193435-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthra[2,3-b:6,7-b']difuran
• 英文别名: Anthra[2,3-b:6,7-b']-difuran；6,16-dioxapentacyclo[11.7.0.03,11.05,9.015,19]icosa-1,3(11),4,7,9,12,14,17,19-nonaene
• CAS: 1193435-28-7
• 化学式: C₁₈H₁₀O₂
• 分子量: 258.276
• InChiKey: SSNNRTUQMYHHFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,6-diacetoxy-3,7-bis(trimethylsilylethynyl)anthracene 在 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 4.0h， 生成 anthra[2,3-b:6,7-b']difuran
  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

• [EN] COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL CONTAINING SAME, ORGANIC SEMICONDUCTOR INK, AND ORGANIC TRANSISTOR<br/>[FR] COMPOSÉ, MATÉRIAU SEMI-CONDUCTEUR ORGANIQUE LE CONTENANT, ENCRE SEMI-CONDUCTRICE ORGANIQUE ET TRANSISTOR ORGANIQUE<br/>[JA] 化合物、並びにそれを含有する有機半導体材料、有機半導体インク及び有機トランジスタ
  申请人：DAINIPPON INK & CHEMICALS

  公开号：WO2015137304A1

  公开（公告）日：2015-09-17

  本発明の課題は、溶剤への溶解性に優れ、複雑なプロセスを経由せずとも容易に、高い移動度の膜を与える、下記一般式（１）で表される化合物、及びそれを用いた有機半導体材料を提供すること、更には、実用的な構成の有機トランジスタを簡便に作製できる有機半導体インクを提供することである。特定の置換基を有するメソゲン骨格からなる化合物は、溶剤溶解性に優れる故に有機半導体インクとしての適性を有し、煩雑な熱処理を必要とせず、簡便な湿式法であっても、上記課題を解決する。上記一般式（１）中のＲ１，Ｒ２，ｐ，ＭＳＧは、請求項１に記載のとおりである。
• Isomerically Pure Anthra[2,3-<i>b</i>:6,7-<i>b</i>′]-difuran (<i>anti</i>-ADF), -dithiophene (<i>anti</i>-ADT), and -diselenophene (<i>anti</i>-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors
  作者：Masahiro Nakano、Kazuki Niimi、Eigo Miyazaki、Itaru Osaka、Kazuo Takimiya

  DOI：10.1021/jo301438t

  日期：2012.9.21

  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).