thieno[3,4-d][1,3]dithiol-2-one | 87207-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: thieno[3,4-d][1,3]dithiol-2-one
• CAS: 87207-39-4
• 化学式: C₅H₂OS₃
• 分子量: 174.268
• InChiKey: BDWQVCPFZQJQLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  356.5±34.0 °C(Predicted)
• 密度：
  1.684±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  thieno[3,4-d][1,3]dithiol-2-one 在 mercury(II) acetate 、 碘 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 8.5h， 生成 4,6-diiodothieno[3,4-d]-1,3-dithiol-2-one
  参考文献：
  名称：

  Synthesis of thieno[3,4-d]-1,3-dithiol-2-one derivatives

  摘要：

  A series of mono-substituted and bis-substituted derivatives of thieno [3,4-d]-1,3-dithiol-2-one were prepared through halogenation, chloromethylation, and subsequent nucleophilic substitution reactions. Compounds were characterized by NMR, FT-IR, and HRMS. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.225
• 作为产物：
  描述：

  thieno[3,4-d]-1,3-dithiol-2-thione 在 mercury(II) diacetate 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 0.5h， 以62%的产率得到thieno[3,4-d][1,3]dithiol-2-one
  参考文献：
  名称：

  通过Me（3）Al促进的有机锡化合物与酯反应合成不对称四硫富瓦烯衍生物。

  摘要：

  描述了通过Me（3）Al促进的有机锡硫醇盐或亚硒酸盐与酯的Me（3）Al促进的反应，构建各种不对称四硫富瓦烯（TTF）的有效合成方法。硫醇锡（3a-c和10）和硒酸酯（3d，5和7）与酯（11a，b）在Me（3）Al作为路易斯酸存在下反应生成二氢四硫富富烯烯衍生物（12、14、15） ，以及17-20）和1,3-二硫杂环丁烷衍生物（13和16）。此外，二硒二硫富瓦烯衍生物（25-28）的合成可以通过Me（3）Al介导的硫醇锡（2a）或硒酸酯（3d和5）与酯（22a，22d和24）的反应来完成。此外，应用Me（3）Al促进硫醇锡（34）与酯（11a-b，22a-d，

  DOI：

  10.1021/jo952255e

文献信息

• The synthesis, redox properties and X-ray crystal structures of two new tetrathiafulvalene-thiophene donors
  作者：Peter J. Skabara、Klaus Müllen、Martin R. Bryce、Judith A. K. Howard、Andrei S. Batsanov

  DOI：10.1039/a803027h

  日期：——

  The functionalisation of tetrathiafulvalene with thiophene units is reported via the synthesis of two multiredox compounds 4 and 5. The two molecules represent a fused structure (4) and a TTF-thiophene system directly linked by a single bond (5); both compounds are endowed with ' 2,5-positions within the thiophene ring, making them accessible to polymerisation reactions. The solution electrochemistry of 4 and 5 reveals the redox properties of the two components: a three-stage oxidation process is seen in each case. Charge-transfer complexes have been prepared, using TCNQ or TCNQF4 as the electron acceptor, with conductivities in the range of 104 to 0.22Scm1. Compounds 4 and 5 have been studied by X-ray crystallography; the former exhibits kappa-packing whilst the latter shows a high degree of conjugation between the two donor moieties.

  报道了四硫富瓦烯与噻吩单元的功能化，通过合成两个多还原化合物4和5。两个分子分别代表一个融合结构（4）和一个通过单键直接连接的TTF-噻吩系统（5）；这两种化合物在噻吩环的2,5-位点上具有可聚合性。对4和5的溶液电化学研究揭示了这两种成分的还原氧化特性：在每种情况下都观察到了三阶段的氧化过程。使用TCNQ或TCNQF4作为电子受体制备了电荷转移复合物，电导率范围为10^4到0.22 S·cm⁻¹。化合物4和5通过X射线晶体学进行了研究；前者表现出κ堆积，而后者则显示出两个供体部分之间高度的共轭性。
• Synthesis and characterisation of new diindenodithienothiophene (DITT) based materials
  作者：Irina Afonina、Peter J. Skabara、Filipe Vilela、Alexander L. Kanibolotsky、John C. Forgie、Ashu K. Bansal、Graham A. Turnbull、Ifor D. W. Samuel、John G. Labram、Thomas D. Anthopoulos、Simon J. Coles、Michael B. Hursthouse

  DOI：10.1039/b919574b

  日期：——

  Three new diindenodithienothiophene (DITT) based materials were synthesised and their electrochemical properties investigated. The HOMO–LUMO gaps were observed to be 3.33, 3.48 and 2.81 eV, respectively. Cyclic voltammetry results indicate increased stability for the alkylated derivatives. The dioxide exhibits strong photoluminescence, giving a photoluminescence quantum yield of 0.72 in solution and 0.14 in the solid state. Hole mobility measurements were carried out on the non-alkylated derivative and the corresponding values were ∼10−4 cm2 V−1 s−1.

  研究人员合成了三种基于二茚二噻吩（DITT）的新材料，并对其电化学特性进行了研究。观察到的 HOMO-LUMO 间隙分别为 3.33、3.48 和 2.81 eV。循环伏安法结果表明，烷基化衍生物的稳定性增强。二氧化物具有很强的光致发光性能，在溶液中的光致发光量子产率为 0.72，在固态中为 0.14。对非烷基化衍生物进行了空穴迁移率测量，其相应值为 ∼10-4 cm2 V-1 s-1。
• Improved Synthesis of the High-Mobility Organic Semiconductor Dithio­phene-Tetrathiafulvalene
  作者：Concepció Rovira、Núria Crivillers、Neil Oxtoby、Marta Mas-Torrent、Jaume Veciana

  DOI：10.1055/s-2007-966053

  日期：2007.6

  Dithiophene-tetrathiafulvalene (DT-TTF) has been shown to be a promising organic semiconductor for organic transistors, since it combines high mobility with processability. A novel synthesis to prepare this material is described here. It involves the coupling of a 1,3-dithiol-2-one. The yield of this route is higher than previously reported yields.

  二噻吩-四硫杂戊烯（DT-TTF）已被证明是一种很有前途的有机半导体，可用于有机晶体管，因为它兼具高迁移率和可加工性。本文介绍了制备这种材料的新型合成方法。它涉及 1,3-二硫醇-2-酮的偶联。该方法的产率高于之前报道的产率。
• Incorporation of fused tetrathiafulvalene units in a DPP–terthiophene copolymer for air stable solution processable organic field effect transistors
  作者：Diego Cortizo-Lacalle、Sasikumar Arumugam、Saadeldin E. T. Elmasly、Alexander L. Kanibolotsky、Neil J. Findlay、Anto Regis Inigo、Peter J. Skabara

  DOI：10.1039/c2jm31502e

  日期：——

  A new terthiophene–diketopyrrolopyrrole (DPP) copolymer has been synthesised in which the central thiophene ring within the terthiophene repeat unit is attached to a fused tetrathiafulvalene (TTF). The electrochemical and absorption data of the polymer, p(DPP-TTF), are presented, and the multi-redox states are investigated by UV-vis spectroelectrochemistry. Bottom gate/bottom contact field effect transistors were fabricated from films of p(DPP-TTF) annealed at 200 °C. The material, which under these conditions forms a fibrous structure, exhibited hole mobilities of 4 ± 2 × 10−2 cm2 V−1 s−1 with an on/off ratio of 1 × 104. The transistors showed little sign of degradation over 15 days of exposure under ambient conditions, demonstrating excellent air-stability. This characteristic is attributed to the incorporation of the TTF unit into the polymer.

  我们合成了一种新的噻吩-二酮吡咯-吡咯（DPP）共聚物，在这种共聚物中，噻吩重复单元中的中心噻吩环连接到融合的四硫杂戊烯（TTF）上。本文介绍了该聚合物 p(DPP-TTF) 的电化学和吸收数据，并通过紫外可见光谱电化学研究了其多重氧化还原状态。在 200 °C 下退火的 p(DPP-TTF) 薄膜制成了底栅/底接触场效应晶体管。这种材料在这些条件下形成了纤维状结构，其空穴迁移率为 4 ± 2 à 10â2 cm2 Vâ1 sâ1，导通/关断比为 1 à 104。在环境条件下暴露 15 天后，晶体管几乎没有降解迹象，显示出极佳的空气稳定性。这一特性归功于聚合物中的 TTF 单元。
• Experimental and theoretical studies into the structural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxaline derivatives
  作者：Peter J. Skabara、Rory Berridge、Karen Prescott、Leonid M. Goldenberg、Enrique Ortí、Rafael Viruela、Rosendo Pou-Amérigo、Andrei S. Batsanov、Judith A. K. Howard、Simon J. Coles、Michael B. Hursthouse

  DOI：10.1039/b003910l

  日期：——

  The syntheses and electrochemistry of thieno[3′,4′∶5,6][1,4]dithiino[2,3-b]quinoxaline (9), 2,3-bis(methylsulfanyl)[1,4]dithiino[2,3-b]quinoxaline (16) and 2,3-ethylenedisulfanyl[1,4]dithiino[2,3-b]quinoxaline (17) are reported, together with the X-ray crystal structures of 9, 16 and the charge-transfer complex 9·TCNQ. In the thieno derivative 9, the molecular structure undergoes a significant change from a boat conformer to a planar system, upon oxidation with TCNQ. Theoretical calculations show that oxidation leads to planarisation of the molecular structure due to the aromatisation of the dithiine moiety. The study of the oxidised/reduced species helps to rationalise the electrochemical behaviour observed experimentally.

  报告了噻吩[3′,4′∶5,6][1,4]二噻嗪[2,3-b]喹喔啉（9）、2,3-双（甲硫基）[1,4]二噻嗪[2,3-b]喹喔啉（16）和2,3-乙撑二硫基[1,4]二噻嗪[2,3-b]喹喔啉（17）的合成和电化学性质，以及9、16的X射线晶体结构和电荷转移复合物9·TCNQ。在噻吩衍生物9中，分子结构在TCNQ氧化后发生了重大变化，从船形构象转变为平面体系。理论计算表明，氧化导致分子结构平面化，这是由于二噻嗪部分的芳香化。对氧化/还原物种的研究有助于解释实验中观察到的电化学行为。