tetraceno[2,3-b]thiophene-5,12-dione | 914922-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: tetraceno[2,3-b]thiophene-5,12-dione
• 英文别名: 6-Thiapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-1(21),3(11),4,7,9,13,15,17,19-nonaene-2,12-dione
• CAS: 914922-86-4
• 化学式: C₂₀H₁₀O₂S
• 分子量: 314.364
• InChiKey: WMDJEMWYLFYWME-UHFFFAOYSA-N

物化性质

• 沸点：
  562.9±19.0 °C(Predicted)
• 密度：
  1.450±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 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：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tetraceno[2,3-b]thiophene-5,12-dione 在 sodium tetrahydroborate 作用下， 生成
  参考文献：
  名称：

  Low-Voltage Organic Transistors Based on Tetraceno[2,3-b]thiophene: Contact Resistance and Air Stability

  摘要：

  The small-molecule organic semiconductor tetraceno[2,3-b]thiophene has been synthesized through an environmentally friendly synthetic route, utilizing NaBH4, rather than Al/HgCl2, for the reduction of the quinone. Low-voltage organic thin-film transistors (TFTs) have been fabricated using tetraceno[2,3-b]thiophene and, for comparison, pentacene and anthradithiophene as the semiconductor. The tetraceno[2,3-b]thiophene TFTs have an effective field-effect mobility as large as 0.55 cm(2) V-1 s(-1) and a subthreshold swing of 0.13 V/decade. In addition, it has been found that the contact resistance of the tetraceno[2,3-b]thiophene TFTs is substantially smaller than that of the anthradithiophene TFTs and similar to that of the pentacene TFTs. The long-term air stability of TFTs based on all three semiconductors has been monitored over a period of 12 months. The initial charge-carrier mobility of the tetraceno[2,3-b]thiophene TFTs is similar to 50% smaller than that of the pentacene TFTs, but as a result of the greater ionization potential and better air stability induced by the terminal thiophene ring condensed at the thiophene-b-bond, the tetraceno[2,3-b]thiophene TFTs outperform the pentacene TFTs after continuous exposure to ambient air for just 3 months.

  DOI：

  10.1021/cm5043183
• 作为产物：
  描述：

  噻吩-2,3-二甲醛 、 1,4-dihydroxyanthracene 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 tetraceno[2,3-b]thiophene-5,12-dione
  参考文献：
  名称：

  Organic Semiconductors and Their Manufacture

  摘要：

  本发明涉及一种半导体器件，包括式I和式XXI的化合物，其中符号的含义在规范中定义，以及式I和XXI的新化合物以及将此类化合物用作有机半导体以制备电子器件，以及规范中给出的其他化合物和器件等其他实施例。

  公开号：

  US20090299070A1

文献信息

• Controlling Single Molecule Conductance by a Locally Induced Chemical Reaction on Individual Thiophene Units
  作者：Tomasz Michnowicz、Bogdana Borca、Rémi Pétuya、Verena Schendel、Marcel Pristl、Ivan Pentegov、Ulrike Kraft、Hagen Klauk、Peter Wahl、Pingo Mutombo、Pavel Jelínek、Andrés Arnau、Uta Schlickum、Klaus Kern

  DOI：10.1002/anie.201915200

  日期：2020.4.6

  understanding of the electronic properties at the individual molecular level and the development of methods to tune the charge transport through molecular junctions. Scanning tunneling microscopy (STM) is an ideal tool not only for the characterization, but also for the manipulation of single atoms and molecules on surfaces. The conductance through a single molecule can be measured by contacting the molecule

  进步基于单分子电子设备的先决条件是更好地理解单个分子水平上的电子性质以及调节通过分子结的电荷传输的方法的发展。扫描隧道显微镜（STM）不仅是表征的理想工具，而且还是处理表面上单个原子和分子的理想工具。通过使单个分子以原子精度接触并在金属STM尖端电极和金属表面电极之间形成分子桥，可以测量通过单个分子的电导。影响电导的参数主要与它们的电子结构以及与金属电极的耦合有关。这里，实验和理论分析着重于单四噻吩噻吩分子，并证明了噻吩部分的原位诱导直接脱硫反应通过在分子碳和铜表面原子之间形成共价键而大大改善了分子锚定。与初始状态相比，该键形成导致电导增加约50％。
• <i>In Situ</i> Reduction and Functionalization of Polycyclic Quinones
  作者：Karl J. Thorley、Yang Song、Sean R. Parkin、John E. Anthony

  DOI：10.1021/acs.orglett.0c02529

  日期：2020.9.18

  Attempts to functionalize polycyclic quinones using lithium diisopropylamide as a base led to the unexpected formation of acenes. This reaction proceeds by electron transfer from the base to the electron deficient quinone, whose radical anion can react with a variety of electrophiles. Siloxy derivatives synthesized by this method could be easily isolated but showed poor photostability. In situ reduced

  尝试使用二异丙基氨基化锂作为碱将多环醌官能化会导致意外的乙炔形成。该反应通过电子从碱转移到缺电子的醌而进行，后者的自由基阴离子可与多种亲电子试剂反应。用这种方法合成的甲硅烷氧基衍生物很容易分离，但光稳定性差。原位减少的中间产物是氧化不稳定的氢醌功能化的简便方法。
• Spectroscopy and Reactivity of Dialkoxy Acenes
  作者：Valentina Brega、Sare Nur Kanari、Connor T. Doherty、Dante Che、Seth A. Sharber、Samuel W. Thomas

  DOI：10.1002/chem.201901258

  日期：2019.8.6

  describes the synthesis, spectroscopic properties, and reactivity with singlet oxygen (1O2) of a series of dialkoxyacenes that vary in the number and types of fused rings in the (hetero)acene cores. Reductive alkylation of quinone precursors yielded target dialkoxyacenes with fused backbones ranging from benzodithiophene to tetracenothiophene. Trends of their experimental spectroscopic characteristics were

  取决于应用，并苯的光化学氧化可以提高或阻碍其功能。尽管在反应位点上带有烷氧基取代基的并苯对于诸如药物输送和有机光电之类的应用很重要，但化学结构对其光化学氧化的影响仍然未知。因此，本文描述了单线态氧（1 O 2）一系列的二烷氧基乙炔，它们在（杂）并苯核心中稠合环的数量和类型各不相同。醌前体的还原烷基化产生目标二烷氧基乙炔，其稠合主链的范围从苯并二噻吩到四噻吩噻吩。其实验光谱特性的趋势与时变密度泛函理论（TD-DFT）的计算结果一致。NMR研究表明，光化学生成1 O 2在有机溶剂中将除这些芳烃中的一种以外的所有芳烃氧化为相应的内过氧化物。这些氧化的速率与稠合的芳烃的数量和类型相关，较长的二烷氧基并烷通常比较短的衍生物快氧化。最后，在酸性氧化环境中照射这些并苯会裂解醚键。这项工作影响了从事有机光电子学的人们，以及对利用功能材料中的光生活性氧种类感兴趣的人们。
• Polyacene and Semiconductor Formulation
  申请人：Anemian Remi Manouk

  公开号：US20080191199A1

  公开（公告）日：2008-08-14

  The invention relates to novel polyacene compounds, organic semiconducting formulations and layers comprising them, a process for preparing the formulation and layer and electronic devices, including organic field effect transistors (OFETs), comprising the same.

  本发明涉及新型聚芴化合物、含有它们的有机半导体配方和层、制备配方和层的过程以及包括它们的电子设备，包括有机场效应晶体管（OFETs）。
• Polyacene and semiconductor Formulation
  申请人：Merck Patent GmbH

  公开号：EP1986247A1

  公开（公告）日：2008-10-29

  The invention relates to novel polyacene compounds, organic semiconducting formulations and layers comprising them, a process for preparing the formulation and layer and electronic devices, including organic field effect transistors (OFETs), comprising the same.

  本发明涉及新型多烯化合物、包含它们的有机半导体配方和层、制备配方和层的工艺以及包含它们的电子器件，包括有机场效应晶体管（OFET）。