tetraceno[2,3-b]thiophene

• 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
• 英文别名: 6-thiapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-1(21),2,4,7,9,11,13,15,17,19-decaene
• 化学式: C₂₀H₁₂S
• 分子量: 284.381
• InChiKey: ZTXYTSSMUSJOIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 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：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  蒽醌 在 四溴化碳 、 四丁基氟化铵 、 氢化铝 、 mercury dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 环己醇 为溶剂， 反应 18.0h， 生成 tetraceno[2,3-b]thiophene
  参考文献：
  名称：

  High-Performance Organic Semiconductors:  Asymmetric Linear Acenes Containing Sulphur

  摘要：

  Two new linear acenes with fused thiophene units have been synthesized. These acenes have conjugation lengths between anthracene and pentacene. Thin films of these linear molecules were characterized by ultraviolet spectroscopy, X-ray diffraction, atomic force microscopy (AFM), and field-effect transistor measurements. Submonolayer AFM studies show growth that greatly resembles pentacene, while thin-film growth is dendritic. Mobilites as high as 0.47 cm2 V-1 s-1 have been found for the tetraceno[2,3-b]thiophene and are as high as 0.15 cm2 V-1 s-1 for anthra[2,3-b]thiophene.

  DOI：

  10.1021/ja066824j

文献信息

• Solution-processed organic micro crystal transistor based on tetraceno[2,3-b]thiophene from a monoketone precursor
  作者：Motonori Watanabe、Ting-Han Chao、Shun-Wei Liu、Ching-Ting Chien、Yuan Jay Chang、Chih-Hsien Yuan、Kuan-Chun Huang、Shu-Hua Chien、Teruo Shinmyozu、Tahsin J. Chow

  DOI：10.1039/c1jm11834j

  日期：——

  The synthesis, thermal and photophysical properties, and solution-processed organic field effect transistors fabricated from a soluble tetraceno[2,3-b]thiophene precursor 1. Compound 1 was synthesised in 9.8% through 6 steps. The TGA profiles showed that a 9.1% weight loss occurred at ca. 130 °C, corresponding to an expulsion of a carbonyl group. The photogeneration of tetraceno[2,3-b]thiophene from 1 in the solution state could be fitted into a first-order rate law with a rate constant (k) of 2.05 × 10−2s−1 in a yield of 55.6% (±0.9%) under a 1.25 mW cm−2 UV lamp. The platelet micro crystals of 1, formed either by heat or by light, were confirmed by XRD to be identical to a simulated one from reported X-ray crystallographic data. The field effect mobility across a single crystal was measured to be 4.75 × 10−1 cm2 V−1s−1 with on/off ratio 105. The high purity of single crystals formed both by heat and by light are supported by an EPR analysis. This is the first report of a solution-processed single-crystal OFET of linear acenes without bulky substituent groups. In another experiment, the devices made directly from an amorphous thin film of 1, prepared by spin-coating, exhibited a charge mobility 3.0 × 10−4 cm2 V−1s−1 with on/off ratio 103.

  合成、热和光物理性质，以及由可溶性四萘[2,3-b]噻吩前体1制成的溶液加工有机场效应晶体管的研究。化合物1通过6个步骤合成，得率为9.8%。热重分析（TGA）表明，在约130°C时发生了9.1%的重量损失，这与羰基的排出相对应。从1中在溶液状态下光生成四萘[2,3-b]噻吩的过程符合一阶速率定律，速率常数（k）为2.05 × 10−2 s−1，产率为55.6%（±0.9%），在1.25 mW cm−2的紫外灯照射下实现。通过X射线衍射（XRD）确认，由热或光形成的1的板状微晶与报告的X射线晶体学数据模拟结果相同。单晶的场效应迁移率测量为4.75 × 10−1 cm2 V−1s−1，开关比为105。通过电子顺磁共振（EPR）分析支持了热和光形成的单晶高纯度。这是首次报告的无大取代基的线性烯烃溶液处理单晶场效应晶体管。在另一项实验中，直接从通过旋涂法制备的无定型薄膜1制成的器件，表现出3.0 × 10−4 cm2 V−1s−1的载流子迁移率，开关比为103。
• 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％。
• TETRACENOTHIOPHENE DERIVATIVES WITH ALKOXY-C-ALKYNE SOLUBILISING UNITS AND THEIR APPLICATIONS AS ORGANIC SEMICONDUCTORS
  申请人：CAMBRIDGE DISPLAY TECHNOLOGY LIMITED

  公开号：US20170133605A1

  公开（公告）日：2017-05-11

  Tetracenothiophene derivatives are disclosed, which comprise alkoxy-C-alkyne solubilising groups at transversal positions of the tetracenothiophene unit. These compounds enable preferential molecular stacking and a high field effect mobility and at the same time show improved solubility as compared to known benzothiophene- and pentacene-based materials. In addition, organic thin films comprising these derivatives, their use in electronic devices and components, such as organic thin film transistors, and methods of manufacturing the same are disclosed.

  本发明揭示了一种四氢萘并噻吩衍生物，其在四氢萘并噻吩单元的横向位置包含烷氧基-C-炔基溶解基团。与已知的基于苯并噻吩和五环芴的材料相比，这些化合物能够实现优先的分子堆积和高场效应迁移率，并且同时显示出改善的溶解性。此外，本发明还揭示了包括这些衍生物的有机薄膜、它们在电子器件和元件中的使用，如有机薄膜晶体管，以及制造它们的方法。
• COMPOSITION FOR FORMING ORGANIC SEMICONDUCTOR FILM, ORGANIC SEMICONDUCTOR FILM AND METHOD FOR MANUFACTURING SAME, AND ORGANIC SEMICONDUCTOR COMPOUND
  申请人：Fujifilm Corporation

  公开号：EP3193383A1

  公开（公告）日：2017-07-19

  Objects of the present invention are to provide a composition for forming an organic semiconductor film that has excellent preservation stability and makes the obtained organic semiconductor element exhibit excellent driving stability in the atmosphere, to provide an organic semiconductor film using the composition for forming an organic semiconductor film, a method for manufacturing the organic semiconductor film, an organic semiconductor element, a method for manufacturing the organic semiconductor element, and to provide a novel organic semiconductor compound. A composition for forming an organic semiconductor film of the present invention contains a specific organic semiconductor having an alkoxyalkyl group as a component A and a solvent as a component B, in which a content of a non-halogen-based solvent is equal to or greater than 50% by mass with respect to a total content of the component B, and a content of the component A is equal to or greater than 0.7% by mass and less than 15% by mass.

  本发明的目的是提供一种用于形成有机半导体薄膜的组合物，该组合物具有优异的保存稳定性，并使获得的有机半导体元件在大气中表现出优异的驱动稳定性；提供一种使用该用于形成有机半导体薄膜的组合物的有机半导体薄膜、一种制造该有机半导体薄膜的方法、一种有机半导体元件、一种制造该有机半导体元件的方法，以及提供一种新型有机半导体化合物。 本发明的一种用于形成有机半导体薄膜的组合物含有一种特定的有机半导体，该半导体具有作为组分 A 的烷氧基烷基和作为组分 B 的溶剂，其中非卤基溶剂的含量相对于组分 B 的总含量等于或大于 50%（按质量计），而组分 A 的含量等于或大于 0.7%（按质量计）且小于 15%（按质量计）。
• Tetracenothiophene derivatives with alkoxy-c-alkyne solubilising units and their applications as organic semiconductors
  申请人：Cambridge Display Technology Limited

  公开号：US10096785B2

  公开（公告）日：2018-10-09

  Tetracenothiophene derivatives are disclosed, which comprise alkoxy-C-alkyne solubilizing groups at transversal positions of the tetracenothiophene unit. These compounds enable preferential molecular stacking and a high field effect mobility and at the same time show improved solubility as compared to known benzothiophene- and pentacene-based materials. In addition, organic thin films comprising these derivatives, their use in electronic devices and components, such as organic thin film transistors, and methods of manufacturing the same are disclosed.

  本发明公开了四烯噻吩衍生物，这些衍生物在四烯噻吩单元的横向位置包含烷氧基-C-炔增溶基团。与已知的以苯并噻吩和并五苯为基础的材料相比，这些化合物能够实现优先分子堆叠和高场效应迁移率，同时显示出更好的溶解性。此外，还公开了包含这些衍生物的有机薄膜、它们在电子设备和元件（如有机薄膜晶体管）中的用途以及制造方法。