2,8-diphenylanthra[2,3-b:6,7-b']difuran | 1397972-53-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2,8-diphenylanthra[2,3-b:6,7-b']difuran
• 英文别名: 2,8-diphenylanthra[2,3-b:6,7-bʹ′]difuran；7,17-Diphenyl-6,16-dioxapentacyclo[11.7.0.03,11.05,9.015,19]icosa-1,3,5(9),7,10,12,14,17,19-nonaene；7,17-diphenyl-6,16-dioxapentacyclo[11.7.0.03,11.05,9.015,19]icosa-1,3,5(9),7,10,12,14,17,19-nonaene
• CAS: 1397972-53-0
• 化学式: C₃₀H₁₈O₂
• 分子量: 410.472
• InChiKey: PFIAAKJPDIRHQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  7.0
• 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-dibromo-3,7-dimethoxyanthracene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三溴化硼 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成 2,8-diphenylanthra[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

• Anthradifuran, a Furan Analogue of Pentacene, and Its Isomers, Exhibiting Solid-state Photoluminescence
  作者：Hayato Tsuji、Kazutaka Shoyama、Eiichi Nakamura

  DOI：10.1246/cl.2012.957

  日期：2012.9.5

  We have synthesized diphenyl-substituted anthra[2,3-b:6,7-b′]difuran, a furan analogue of pentacene, together with its isomers, anthra[2,1-b:6,5-b′]difuran and anthra[1,2-b:5,6-b′]difuran. These compounds are stable in the solid state with high decomposition temperatures. They are luminescent in the solid state with a quantum yield of 0.093–0.23.

  我们合成了二苯基取代的蒽[2,3-b:6,7-b′]二呋喃（一种五碳烯的呋喃类似物）及其异构体蒽[2,1-b:6,5-b′]二呋喃和蒽[1,2-b:5,6-b′]二呋喃。这些化合物固态稳定，分解温度高。它们在固态下发光，量子产率为 0.093-0.23。
• [EN] METHOD FOR SYNTHESIZING ANTI-ANTHRADICHALCOGENOPHENE<br/>[FR] PROCÉDÉ POUR SYNTHÉTISER UN ANTI-ANTHRADICHALCOGÉNOPHÈNE
  申请人：UNIV HIROSHIMA NAT UNIV CORP

  公开号：WO2014024769A1

  公开（公告）日：2014-02-13

  　ａｎｔｉ－アントラジカルコゲノフェンの合成方法は、式１で表される化合物とハロゲン化剤とを反応させて、式２で表される化合物を得る工程と、式２で表される化合物と脱アルキル化剤とを反応させて、式３で表される化合物を得る工程と、式３で表される化合物とアセチル化剤とを反応させて、式４で表される化合物を得る工程と、式４で表される化合物と末端アセチレン化合物とを反応させて、式５で表される化合物を得る工程と、式５で表される化合物に塩基を作用させて環化させ、式６で表される化合物を得る工程と、を含む。式中、Ｒ１はアルキル基を表し、Ｘはハロゲンを表し、Ａｃはアセチル基を表し、Ｒ２はトリメチルシリル基、フェニル基又はアルキル基、Ｒ３は水素、フェニル基又はアルキル基を表す。
• 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).