thieno(2,3-d)-1,3-dithiol-2-thione | 67188-88-9

• 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(2,3-d)-1,3-dithiol-2-thione
• 英文别名: Thieno[2,3-d][1,3]dithiole-2-thione
• CAS: 67188-88-9
• 化学式: C₅H₂S₄
• mdl: MFCD01556892
• 分子量: 190.335
• InChiKey: JSQDAIJLARMFIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  111
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  thieno(2,3-d)-1,3-dithiol-2-thione 在 三甲氧基磷 作用下， 以22%的产率得到α-dithiophenetetrathiafulvalene
  参考文献：
  名称：

  Novel Selenocycle-Fused TTF-Type of Electron Donors Forming Conducting Molecular Complexes:  Bis(ethyleneseleno)tetrathiafulvalene (BES-TTF), Diselenolotetrathiafulvalene (DS-TTF), and Bis(ethyleneseleno)tetraselenafulvalene (BES-TSF)

  摘要：

  The title selenocycle-fused tetrathiafulvalene derivatives (BES-TTF and DS-TTF) and tetraselenafulvalene derivative (BES-TSF) have been synthesized as novel electron donors, and their conducting molecular complexes have been studied. Although DS-TTF formed only semiconducting complexes, BES-TTF and BES-TSF gave metallic complexes with various electron accepters, such as TCNQ, ClO4-, PF6-, and AsF6-. Among them, the TCNQ complex of BES-TSF showed an extraordinarily high room-temperature conductivity of 2700 +/- 500 S cm(-1), which is of the highest class for a molecular complex. The complexes of BES-TTF underwent a typical metal-to-insulator transition at low temperature, characteristic of one-dimensional organic metals. On the other hand, complexes of BES-TSF were less temperature-dependent and remained highly conducting, even down to cryogenic temperature. The different behaviors of the three donors are discussed on the basis of the crystal structures of their representative complexes as elucidated by X-ray crystallographic analyses.

  DOI：

  10.1021/jo981024f
• 作为产物：
  描述：

  4,5-Dihydrothieno[2,3-d]-1,3-dithiol-2-thion 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以60%的产率得到thieno(2,3-d)-1,3-dithiol-2-thione
  参考文献：
  名称：

  Novel Selenocycle-Fused TTF-Type of Electron Donors Forming Conducting Molecular Complexes:  Bis(ethyleneseleno)tetrathiafulvalene (BES-TTF), Diselenolotetrathiafulvalene (DS-TTF), and Bis(ethyleneseleno)tetraselenafulvalene (BES-TSF)

  摘要：

  The title selenocycle-fused tetrathiafulvalene derivatives (BES-TTF and DS-TTF) and tetraselenafulvalene derivative (BES-TSF) have been synthesized as novel electron donors, and their conducting molecular complexes have been studied. Although DS-TTF formed only semiconducting complexes, BES-TTF and BES-TSF gave metallic complexes with various electron accepters, such as TCNQ, ClO4-, PF6-, and AsF6-. Among them, the TCNQ complex of BES-TSF showed an extraordinarily high room-temperature conductivity of 2700 +/- 500 S cm(-1), which is of the highest class for a molecular complex. The complexes of BES-TTF underwent a typical metal-to-insulator transition at low temperature, characteristic of one-dimensional organic metals. On the other hand, complexes of BES-TSF were less temperature-dependent and remained highly conducting, even down to cryogenic temperature. The different behaviors of the three donors are discussed on the basis of the crystal structures of their representative complexes as elucidated by X-ray crystallographic analyses.

  DOI：

  10.1021/jo981024f

文献信息

• Synthesis of Thieno[2,3-d]-1,3-dithiol-2-thiones from Thieno[2,3-d]-1,2,3-thiadiazoles: Matryoshka-type autoclave for high-temperature, high-pressure thermolysis microscale reactions
  作者：Ulrich Jordis、Kaberi Bhattacharya、Philip Boamah、Ving Lee

  DOI：10.3390/70200145

  日期：——

  Thieno[2,3-d]-1,2,3-thiadiazoles (1) react with carbon disulfide in a "Matryoshka-type" double compartment autoclave [1] to yield thieno[2,3-d]-1,3-dithiol-2-thiones (2). With BH3/Me2S the cyclic trithiocarbonate (2d) is cleaved and the product characterized after methylation as 4b. Compounds 7a and 7b are prepared via the thieno[2,3-d]-1,3-dithiolium salts (6) followed by NaBH4-reduction.

  Thieno [2,3-d] -1,2,3-噻二唑 (1) 在“Matryoshka 型”双室高压釜 [1] 中与二硫化碳反应生成噻吩 [2,3-d] -1.3-二硫醇-2-硫酮 (2)。用 BH3/Me2S 裂解环状三硫代碳酸酯 (2d)，甲基化后产物表征为 4b。化合物7a和7b通过噻吩并[2,3-d]-1,3-二硫鎓盐(6)随后NaBH4还原制备。
• A Soluble α-Dithienotetrathiafulvalene Derivative for Organic Field-effect Transistors
  作者：Iori Doi、Kiyotaka Goshome、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1246/cl.2012.435

  日期：2012.4.5

  Bis(octylthio) derivative of α-dithienotetrathiafulvalene (α-DT-TTF) was synthesized, characterized, and examined as a semiconductor for organic field-effect transistors (OFETs). In contrast to no field-effect responses of devices based on evaporated thin-film of the parent α-DT-TTF, the octylthio derivative afforded solution-processed OFETs showing apparent normally-on behaviors with field-effect mobility of up to 0.6 cm2 V−1 s−1. Characterization of the thin-film revealed that the octylthio groups had significant impact on self-assembly, affording high quality thin films with well-oriented molecular array.

  合成了α-二噁烷四硫杂环（α-DT-TTF）的双（辛基硫）衍生物，并对其进行了表征，作为有机场效应晶体管（OFETs）的半导体进行了研究。与基于蒸发薄膜的母体α-DT-TTF的器件没有场效应响应相比，辛基硫衍生物则提供了显示出明显正常导通特性的溶液处理OFETs，其场效应迁移率高达0.6 cm² V⁻¹ s⁻¹。薄膜的表征表明，辛基硫基团对自组装有显著影响，使薄膜具有高质量的良好取向分子阵列。
• Synthesis of Several Isomeric Tetrathiafulvalene .pi.-Electron Donors with Peripheral Sulfur Atoms. A Study of Their Radical Cations
  作者：Concepcio Rovira、Jaume Veciana、Nuria Santalo、Judit Tarres、Joan Cirujeda、Elies Molins、Jordi Llorca、Enrique Espinosa

  DOI：10.1021/jo00091a017

  日期：1994.6

  An efficient synthesis of one new (10) and three previously reported (9, 11, and 12) pi-electron donors, which have one sulfur atom in each of the outer five-membered rings attached to the TTF system, is presented. The radical cations derived from 9-11 have been studied by ESR spectroscopy and the spin density distribution of these radical cations, as well as those of other related radical cations, have been determined by MO calculations and correlated with the ESR spectral data. The single-crystal X-ray structures of pi-donors 9 and 12 are reported. The most remarkable fact of these structures is the transverse intermolecular contacts between interstacked molecules. The external sulfur atoms of 9 play a central role in its transverse structural pattern. Complexes of donors 9 and 10 with tetracyano-p-quinodimethane (TCNQ) and tetrafluorotetracyano-p-quinodimethane (TC-NQF(4)) have been obtained and characterized.
• Synthesis and mass spectrometric study of condensed thiones: Precursors of thiophene heterofulvalenes
  作者：V. P. Litvinov、I. A. Dzhumaev、B. M. Zolotarev

  DOI：10.1007/bf00954669

  日期：1983.9
• Condensed heteroaromatic 1,3-dithiol-2-thiones and their selenium analogs
  作者：V. P. Litvinov、I. A. Dzhumaev

  DOI：10.1007/bf00949809

  日期：1982.3