6,13-di(2-thienyl)-6,13-pentacenediol | 874438-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 6,13-di(2-thienyl)-6,13-pentacenediol
• 英文别名: 6,13-dihydro-6,13-dithien-2-ylpentacene-6,13-diol；6,13-di(thiophen-2-yl)-6,13-dihydropentacene-6,13-diol；6,13-Dithiophen-2-ylpentacene-6,13-diol
• CAS: 874438-79-6
• 化学式: C₃₀H₂₀O₂S₂
• 分子量: 476.62
• InChiKey: VUMBAATZAJKPFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,13-di(2-thienyl)-6,13-pentacenediol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以44.5%的产率得到13,13-dithien-2-ylpentacene-6-one
  参考文献：
  名称：

  Reduction versus Rearrangement of 6,13-Dihydro-6,13-diarylpentacene-6,13-diols Affording 6,13- and 13,13′-Substituted Pentacene Derivatives

  摘要：

  并五苯具有优异的半导电特性，但在有机薄膜晶体管（OTFT）中的实际应用引发了诸多问题，主要由其对氧气的敏感性和极低的溶解度所致。为了解决使用并五苯所涉及的问题，在6位和13位引入了不同的芳基取代基。对于富电子芳基取代基，并五苯环系的形成可能伴随着起始的二氢并五苯二醇重排为13,13′-二取代的并五苯-6-酮。此外，还制备了6-单取代的并五苯。

  DOI：

  10.1055/s-2004-836055
• 作为产物：
  描述：

  6,13-五并苯醌 、 magnesium,2H-thiophen-2-ide,bromide 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 6,13-di(2-thienyl)-6,13-pentacenediol
  参考文献：
  名称：

  Organization of Acenes with a Cruciform Assembly Motif

  摘要：

  This study explores the assembly in the crystalline state of a class of pentacenes that are substituted along their long edges with aromatic rings forming rigid, cruciform molecules. The crystals were grown from the gas phase, and their structures were compared with DFT-optimized geometries. Both crystallographic and computed structures show that a planar acene core is the exception rather than the rule. In the assembly of these molecules, the phenyl groups block the herringbone motif and further guide the arrangement of the acene core into higher order structures. The packing for the phenyl-substituted derivatives is dictated by close contacts between the C-H's of the pendant aromatic rings and the carbons at the fusions in the acene backbone. Using thiciphene substituents instead of phenyls creates cofacially stacked acenes. In thin films, the thiophene-substituted derivative forms devices with good electrical properties: relatively high mobility, high ON/OFF ratios, and low threshold voltage for device activation. An unusual result is obtained for the decaphenyl pentacene when devices are fabricated on its crystalline surface. Although its acene cores are well isolated from each other, this material still exhibits good electrical properties.

  DOI：

  10.1021/ja0570786

文献信息

• Increased photooxidation stability of pentacene derivatives linked with aromatic groups for OTFTs
  作者：Dong-Su Kim、Ji Eun Jung、Nam Seob Baek、Tae-Dong Kim

  DOI：10.1016/j.orgel.2014.11.025

  日期：2015.2

  Pentacene derivatives linked with aromatic groups at the 6,13-positions have been synthesized and characterized for their photooxidation properties. They exhibit high solubility which provides low-cost solution deposition methods. However, most of them are highly susceptible to photooxidation in solution determined with a few minutes of their half-life time under ambient conditions, practically precluding them from solution fabrication applications. Interestingly, their photooxidation stability can be significantly increased by blocking out light. The thin film transistor device for 3,4,5-trifluorophenyl-substituted pentacene (2c) showed the highest mobility of 1.1 x 10(-2) cm(2) V-1 s(-1) with the threshold voltage of 20 V when it was prepared in the dark condition. (C) 2014 Elsevier B.V. All rights reserved.