2-<4,5-bis(2-cyanoethylsulfanyl)-1,3-dithiol-2-ylidene>-4,5-bis(butylsulfanyl)-1,3-dithiole | 176384-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: 2-<4,5-bis(2-cyanoethylsulfanyl)-1,3-dithiol-2-ylidene>-4,5-bis(butylsulfanyl)-1,3-dithiole
• 英文别名: 2,3-bis(butylthio)-6,7-bis(2-cyanoethylthio)tetrathiofulvalene；2-[4,5-bis(2-cyanoethylsulfanyl)-1,3-dithiol-2-ylidene]-4,5-bis(butylsulfanyl)-1,3-dithiole；3,3'-[[2-[4,5-bis(butylthio)-1,3-dithiol-2-ylidene]-1,3-dithiole-4,5-diyl]bis(thio)]bis(propanenitrile)；3-[[2-[4,5-bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5-(2-cyanoethylsulfanyl)-1,3-dithiol-4-yl]sulfanyl]propanenitrile
• CAS: 176384-05-7
• 化学式: C₂₀H₂₆N₂S₈
• 分子量: 550.968
• InChiKey: JMDPXVZOMOJUOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  250
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-<4,5-bis(2-cyanoethylsulfanyl)-1,3-dithiol-2-ylidene>-4,5-bis(butylsulfanyl)-1,3-dithiole 在 I₂ 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, structure and properties of nickel complexes of 4,5-tetrathiafulvalene dithiolates: high conductivity in neutral dithiolate complexes

  摘要：

  取代的 TTF 二硫醇盐配体的双阴离子和中性镍络合物已被制备，中性络合物的室温电导率高达 10–1 S cm–1；报道了中性络合物[Ni(C10H10S8)2]的晶体结构。

  DOI：

  10.1039/cc9960001363
• 作为产物：
  描述：

  4,5-双(2-氰乙基硫代)-1,3-二硫醇-2-硫酮 在 mercury(II) diacetate 、 亚磷酸三乙酯 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 2-<4,5-bis(2-cyanoethylsulfanyl)-1,3-dithiol-2-ylidene>-4,5-bis(butylsulfanyl)-1,3-dithiole
  参考文献：
  名称：

  Narvor, Nathalie Le; Robertson, Neil; Wallace, Emma, Journal of the Chemical Society, Dalton Transactions, 1996, # 6, p. 823 - 828

  摘要：

  DOI：

文献信息

• (Trialkoxysilyl)tetrathiafulvalenes: Precursors of Organized Organic-Inorganic Hybrid Materials by Sol-Gel Chemistry
  作者：Nathalie Bellec、Fr�d�ric Lerouge、Beno�t Pichon、Genevi�ve Cerveau、Robert�J.�P. Corriu、Dominique Lorcy

  DOI：10.1002/ejoc.200400485

  日期：2005.1

  The synthesis, characterization and electrochemical behaviour of novel monomers for use in sol-gel processes are described. These new compounds include a rigid tetrathiafulvalene (TTF) core substituted by one or two spacers, to which a triethoxysilyl group is covalently bonded. The synthesis is based on the preparation of various cyanoethyl-protected TTF thiolates, deprotection and alkylation of thiolate

  描述了用于溶胶-凝胶过程的新型单体的合成、表征和电化学行为。这些新化合物包括被一个或两个间隔基取代的刚性四硫富瓦烯 (TTF) 核，三乙氧基甲硅烷基与该核共价键合。该合成基于各种氰乙基保护的 TTF 硫醇盐的制备，硫醇盐与 2-溴乙醇的脱保护和烷基化，以及醇官能团与 3-(三乙氧基甲硅烷基)丙基异氰酸酯的后续缩合。已通过电化学研究研究了标题化合物的供体能力。这些新前体的水解缩聚反应是在 THF 溶液中在亲核试剂（四丁基氟化铵，TBAF）或酸（HCl）催化剂存在下进行的。所得混合固体高度缩聚，并在纳米（X 射线衍射）和微米（双折射）尺度上呈现组织。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• A Novel Tetra(tetrathiafulvalene-Thiacrown Ether)-Substituted Porphyrazine: Synthesis, Electrochemical, and Control Aggregation in Solution by Complexation of Transition-Metal Ions
  作者：Bingzhu Yin、Cuiping Jiang

  DOI：10.3987/com-09-11876

  日期：——

  Synthesis of a novel magnesium porphyrazine 6, peripherally substituted with S 4 crown ether-TTF macrocycles was described. Molecular structure has been fully characterized by 1 H-NMR, IR, MS, and elemental analysis. Crystal structure of the precursor was determined by X-ray crystallography. Their solution electrochemical data showed two reductive and three oxidative processes within a -1.3 V to -1

  描述了一种新型镁卟啉 6 的合成，外围被 S 4 冠醚-TTF 大环取代。分子结构已通过 1 H-NMR、IR、MS 和元素分析充分表征。前体的晶体结构通过 X 射线晶体学确定。他们的溶液电化学数据显示在 -1.3 V 至 -1.5 V 电位窗口内有两个还原过程和三个氧化过程。紫外/可见光谱和电子顺磁共振 (EPR) 测量揭示了四氮杂卟啉 6 与 F 4 TCNQ 之间形成电荷转移复合物。紫外/可见光谱表明过渡金属离子的添加​​导致四氮杂卟啉配合物的二聚化。
• Tetrakis(tetrathiafulvalene-tetrathiacrown ether)porphyrazine Triads: Synthesis, Photophysical, and Electrochemical Properties
  作者：Ruibin Hou、Bao Li、Keli Zhong、Hongda Li、Long-Yi Jin、Bingzhu Yin

  DOI：10.1002/ejoc.201101484

  日期：2012.2

  ane (F4TCNQ) to form a charge-transfer complex, which exhibits absorption bands at around 760 and 860 nm. Selected triads 4a and 5a bind silver(I) and mercury(II) ions. In the case of triad 4a, the addition of silver(I) ions led to dimerization of the triad, which fragmented to form monomeric 4:1 host–guest complexes when more than 2 equiv. of the metal ions were added. X-ray scattering at room temperature

  合成并表征了一系列在外围具有长而柔韧的脂肪族侧链的四（四硫富瓦烯-四硫冠醚）四氮杂卟啉三联体。电化学研究显示两个可逆的四电子氧化波、一个可逆的单电子氧化波和两个不可逆的单电子还原波，表明这些三元组是良好的 π 电子供体。选定的三元组 4a 与 2,3,5,6-四氟-7,7,8,8-四氰基醌二甲烷 (F4TCNQ) 反应形成电荷转移复合物，其在 760 和 860 nm 附近表现出吸收带。选定的三元组 4a 和 5a 结合银 (I) 和汞 (II) 离子。在三元组 4a 的情况下，银 (I) 离子的添加​​导致三元组的二聚化，当超过 2 当量时，三元组分裂成单体 4:1 的主客体复合物。添加金属离子。室温下的 X 射线散射表明，三元组 5c 在块体状态下是一种高度有序的斜柱状结构。前体3b、c的晶体结构也通过X射线衍射分析确定。
• New tetrathiafulvalene fused-naphthalene diimides for solution-processible and air-stable p-type and ambipolar organic semiconductors
  作者：Luxi Tan、Yunlong Guo、Yang Yang、Guanxin Zhang、Deqing Zhang、Gui Yu、Wei Xu、Yunqi Liu

  DOI：10.1039/c2sc20303k

  日期：——

  New conjugated electron donor–acceptor molecules with tetrathiafulvalene (TTF) fused-naphthalene diimide frameworks (1–6) are synthesized and investigated. The NDI cores are flanked by TTF and 2-(1,3-dithiol-2-ylidene)malonitrile moieties within 1–3, whereas compounds 4–6 contain two TTF moieties. Based on cyclic voltammetric and absorption spectral studies, the LUMO and HOMO energies of 1–3 are estimated to be ca. −4.3 eV and ca. −5.1 eV, and those of 4–6 are ca. −4.1 eV and ca. −5.0 eV, respectively. These values are consistent with theoretical calculations. Thin films of 1–6 are easily prepared with the spin-coating technique and the resulting OFETs are successfully fabricated with conventional procedures. The OFETs results reveal that compounds 1–3 behave as ambipolar semiconductors and 4–6 as p-type semiconductors. Among 1–3, compound 3 exhibits relatively high hole and electron mobilities in air, reaching 0.03 and 0.003 cm2 V−1 s−1, respectively, after annealing at 160 °C. The OFET based on a thin film of 5 shows the best performance with μh = 0.31 cm2 V−1 s−1, Ion/off = 104 among compounds 4–6 after annealing at 160 °C. The thin films of 1–6 are investigated with XRD and AFM, and the data can well interpret the variation of carrier mobilities of 1–6 after annealing. Moreover, the influences of alkyl chains in 1–6 on the intermolecular arrangements and carrier mobilities are also discussed.

  合成并研究了具有四噻富戊二烯（TTF）融合萘二亚胺框架（1-6）的新型共轭电子供体-受体分子。在 1-3 号化合物中，NDI 核心的两侧分别是 TTF 和 2-(1,3- 二硫醇-2-亚基)丙二腈分子，而 4-6 号化合物则含有两个 TTF 分子。根据循环伏安法和吸收光谱研究，估计 1-3 的 LUMO 和 HOMO 能量分别约为 -4.3 eV 和 -4.3 eV。4.3 eV 和 -5.1 eV。5.1 eV，4-6 的能量分别约为 -4.1 eV 和 -5.1 eV。-4.1eV和-5.0 eV。这些数值与理论计算结果一致。利用旋涂技术可以轻松制备 1-6 薄膜，并通过传统方法成功制造出 OFET。OFET 的结果表明，化合物 1-3 表现为双极性半导体，化合物 4-6 表现为 p 型半导体。在 1-3 种化合物中，化合物 3 在空气中表现出相对较高的空穴和电子迁移率，在 160 °C 退火后分别达到 0.03 和 0.003 cm2 V-1 s-1。基于 5 薄膜的 OFET 在 160 °C 退火后，在 4-6 化合物中显示出最佳性能，μh = 0.31 cm2 V-1 s-1，离子/关 = 104。利用 XRD 和原子力显微镜对 1-6 薄膜进行了研究，这些数据可以很好地解释 1-6 在退火后载流子迁移率的变化。此外，还讨论了 1-6 中烷基链对分子间排列和载流子迁移率的影响。
• Metal complexes of a tetrathiafulvalene 4,5-dithiolate. Synthesis, characterisation and properties of dianionic and neutral mercury complexes
  作者：Nathalie Le Narvor、Neil Robertson、Emma Wallace、Jeremy D. Kilburn、Allan E. Underhill、Philip N. Bartlett、Michael Webster

  DOI：10.1039/dt9960000823

  日期：——

  Dianionic mercury bis(tetrathiafulvalene dithiolate) complexes [NMe4]2[Hg(R2C6S8)2](R = Et or Bu) and the corresponding oxidised neutral complex [Hg(R2C6S8)2](R = Et) have been prepared. The crystal structure of [NMe4]2[Hg(R2C6S8)2](R = Et) has been determined and shows that the tetrathiafulvalene dithiolate units are tetrahedrally co-ordinated around the central Hg atom. Cyclic voltammetry and ESR studies indicated that there is very little interaction between the two ligands. A compressed pellet of the powdered neutral complex exhibited an electrical conductivity of 10–5 S cm–1 at room temperature.

  制备了滇离子双（四硫富戊烯二硫酸盐）汞络合物 [NMe4]2[Hg(R2C6S8)2](R = Et 或 Bu) 以及相应的氧化中性络合物 [Hg(R2C6S8)2](R = Et)。[NMe4]2[Hg(R2C6S8)2](R = Et)的晶体结构已经确定，并显示出四硫富戊二烯二硫酸盐单元围绕中心汞原子呈四面体配位。循环伏安法和 ESR 研究表明，这两种配体之间的相互作用非常小。粉末状中性复合物的压缩颗粒在室温下的电导率为 10-5 S cm-1。