4,6-dihydrothieno[3,4-d]-1,3-dithiol-2-thione | 127501-72-8

• 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: 4,6-dihydrothieno[3,4-d]-1,3-dithiol-2-thione
• 英文别名: 4,6-dihydro-[3,4-d]-thieno-1,3-dithiole-2-thione；4,6-dihydrothieno[3,4-d][1,3]dithiole-2-thione
• CAS: 127501-72-8
• 化学式: C₅H₄S₄
• 分子量: 192.351
• InChiKey: LVIAWDMRDBWWEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dihydrothieno[3,4-d]-1,3-dithiol-2-thione 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 1.5h， 以96%的产率得到thieno[3,4-d]-1,3-dithiol-2-thione
  参考文献：
  名称：

  The synthesis, redox properties and X-ray crystal structures of two new tetrathiafulvalene-thiophene donors

  摘要：

  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。

  DOI：

  10.1039/a803027h
• 作为产物：
  描述：

  4,5-Bis(hydroxymethyl)-1,3-dithiole-2-thione 在 sodium sulfide 、 四溴化碳 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 4,6-dihydrothieno[3,4-d]-1,3-dithiol-2-thione
  参考文献：
  名称：

  The synthesis, redox properties and X-ray crystal structures of two new tetrathiafulvalene-thiophene donors

  摘要：

  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。

  DOI：

  10.1039/a803027h

文献信息

• Bis(thiodimethylene)-tetrahiafulvalene (BTDM-TTF). A new π-electron donor with relevant oxidation properties
  作者：C. Rovira、N. Santalō、J. Veciana

  DOI：10.1016/s0040-4039(01)93950-4

  日期：1989.1

  The synthesis and some physical properties of a new thioalkyl substituted tetrathiafulvalene, bis(thiodimethylene)tetrathiafulvalene, are reported. Oxidation potentials of BTDM-TTF indicate a low intramolecular Coulomb repulsion energy.

  报道了新的硫代烷基取代的四硫富瓦烯双（硫代二亚甲基）四硫富瓦烯的合成和一些物理性质。BTDM-TTF的氧化电位表明分子内库仑排斥能低。
• 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.
• Skabara, Peter J.; Serebryakov, Igor M.; Perepichka, Igor F., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 3, p. 505 - 513
  作者：Skabara, Peter J.、Serebryakov, Igor M.、Perepichka, Igor F.

  DOI：——

  日期：——
• Correlation between Crystal Structure and Mobility in Organic Field-Effect Transistors Based on Single Crystals of Tetrathiafulvalene Derivatives
  作者：Marta Mas-Torrent、Peter Hadley、Stefan T. Bromley、Xavi Ribas、Judit Tarrés、Montserrat Mas、Elies Molins、Jaume Veciana、Concepció Rovira

  DOI：10.1021/ja048342i

  日期：2004.7.14

  Recently, it was reported that crystals of the organic material dithiophene-tetrathiafulvalene (DT-TTF) have a high field-effect charge carrier mobility of 1.4 cm(2)/(V(.)s). These crystals were formed by a simple drop-casting method, making this material interesting to investigate for possible applications in low-cost electronics. Here, organic single-crystal field-effect transistors based on materials related to DT-TTF are presented and a clear correlation between the crystal structure and the electrical characteristics is observed. The observed relationship between the mobilities in the different crystal structures is strongly corroborated by calculations of both the molecular reorganization energies and the maximum intermolecular transfer integrals. The most suitable materials described here exhibit mobilities that are among the highest reported for organic field-effect transistors and that are the highest reported for solution-processed materials.
• ROVIRA, C.;SANTALO, N.;VECIANA, J., TETRAHEDRON LETT., 30,(1989) N1, C. 7249-7252
  作者：ROVIRA, C.、SANTALO, N.、VECIANA, J.

  DOI：——

  日期：——