4',5'-dimethyl-4,5-(ethylenedithio)-1',3'-diselena-1,3-dithiafulvalene | 101683-17-4

• 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: 4',5'-dimethyl-4,5-(ethylenedithio)-1',3'-diselena-1,3-dithiafulvalene
• 英文别名: dimethyl(ethylenedithio)diselenadithiafulfalene；dimethyl(ethylenedithio)diselenadithiafulvalene；dimethyl{ethylenedithio}diselenadithiafulvalene；DMET；ethylenedithiodimethyldithiadiselenafulvalene；2-(4,5-Dimethyl-1,3-diselenol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiine
• CAS: 101683-17-4
• 化学式: C₁₀H₁₀S₄Se₂
• 分子量: 416.373
• InChiKey: QEBNVGLWXKVRJR-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205 °C
• 沸点：
  416.8±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4',5'-dimethyl-4,5-(ethylenedithio)-1',3'-diselena-1,3-dithiafulvalene 在 tetrabutylammonium tetrafluoroborate 作用下， 以 1,1,2-三氯乙烷 为溶剂， 生成 5,6-dihydro-2-(4,5-dimethyl-1,3-diselenol-2-ylidene)dithiolo<4,5-b><1,4>dithiinium tetrafluoroborate
  参考文献：
  名称：

  Crystal Structure of the Organic Metal (DMET)₂BF₄with Two Columns along Two Crystallographic Axes

  摘要：

  (DMET)2BF4：5,6-二氢-2-(4,5-二甲基-1,3-二硒醇-2-亚基)二硫醇[4,5-b][1,4]二硫鎓四氟硼酸盐（2:1），（C10H10S4Se2）2BF4的水晶结构已确定。晶体数据：Mr=919.49，三斜晶，P\bar1，a=7.032(2)，b=7.812(3)，c=27.502(11) Å，α=90.87(2)，β=90.28(2)，γ=106.22(2)°，V=1450.5(15) Å3，Z=2，Dx=2.11 Mg m−3，λ(Mo Kα)=0.71068 Å，μ=5.60 mm−1，F(000)=890，T=297 K，R=0.077（4600个反射）。两个晶体学上独立的DMET分子分别沿着几乎垂直的方向形成柱状结构，有序的BF4阴离子位于DMET柱之间。

  DOI：

  10.1246/bcsj.64.212
• 作为产物：
  描述：

  4,5-二甲基-2-硒氧代-1,3-二硒醚 在 甲基溴化镁 、 二丁基二氯化锡 、 mercury(II) diacetate 、 三甲基铝 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 0.67h， 生成 4',5'-dimethyl-4,5-(ethylenedithio)-1',3'-diselena-1,3-dithiafulvalene
  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

• Unsymmetrically substituted dithiadiselenafulvalene donors for organic metals. Synthesis and conductivity of the charge-transfer salts
  作者：Koichi Kikuchi、Takahisa Namiki、Lsao Ikemoto、Keiji Kobayashi

  DOI：10.1039/c39860001472

  日期：——

  New unsymmetrical dithiadiselenafulvalene donors and their radical cation salts with inorganic anions have been prepared; among the salts dimethyl(ethylenedithio)dithiadiselenafulvalene salts exhibit the highest electrical conductivity.

  制备了新的不对称二硫代二富硒烯戊烯供体及其与无机阴离子的自由基阳离子盐。在盐中，二甲基（亚乙基二硫代）二硫代二富马烯戊烯盐显示出最高的电导率。
• Electronic and Magnetic Properties of Organic Conductors (DMET)₂MBr₄(M = Fe, Ga)
  作者：Kengo Enomoto、Jun-Ichi Yamaura、Akira Miyazaki、Toshiaki Enoki

  DOI：10.1246/bcsj.76.945

  日期：2003.5

  (DMET)2MBr4 (M = Fe, Ga) are isostructural organic conductors whose crystal structure consists of an alternate stacking of quasi one-dimensional chain-based donor layers and anion square lattices. The resistivity, ESR, magnetic susceptibility, magnetization, and magnetoresistance of these salts were investigated in order to clarify the correlation between the electronic structure and the magnetism. The electronic structures of both salts are metallic down to TMI ∼40 K, below which a Mott insulating state is stabilized, accompanied by an SDW transition at TSDW ∼25 K. The FeBr4 salt with Fe3+ (S = 5/2) localized spins undergoes an antiferromagnetic transition at TN = 3.7 K. In the FeBr4 salt, the magnetization curves, which show field-direction-dependent anomalies in addition to a spin-flop transition, are demonstrated to have a participation of donor π-electron spins in the magnetization processes. The field dependence of the magnetoresistances below TN tracks faithfully that of the magnetization, where the donor π-electrons and Fe3+ d-electrons are responsible for the former and the latter, respectively. This clearly demonstrates the presence of the π–d interaction that plays an important role in the interplay between electron transport and magnetism.

  (DMET)2MBr4（M = Fe、Ga）是等结构有机导体，其晶体结构由准一维链基供体层和阴离子方格交替堆叠组成。为了明确电子结构与磁性之间的相关性，我们对这些盐的电阻率、ESR、磁感应强度、磁化率和磁阻进行了研究。这两种盐的电子结构在 TMI ∼40 K 时都是金属性的，在此温度以下则稳定为莫特绝缘态，并在 TSDW ∼25 K 时发生 SDW 转变。在 FeBr4 盐中，除了自旋翻转转变外，磁化曲线还显示出随场方向变化的异常现象，这表明在磁化过程中有供体 π 电子自旋的参与。TN以下磁阻的磁场依赖性忠实地跟踪了磁化的磁场依赖性，供体π电子和Fe3+ d电子分别对前者和后者负责。这清楚地表明了π-d相互作用的存在，它在电子传输和磁性之间的相互作用中发挥了重要作用。
• New Charge-transfer Salts Based on Unsymmetrical Donor DMET and Metal Complex Anions: (DMET)₃[Cr(isoq)₂(NCS)₄] and (DMET)₃[Cr(phen)(NCS)₄]·CH₃CN
  作者：Masamichi Umemiya、Makoto Goto、Norihito Kobayashi、Shinya Takaishi、Takashi Kajiwara、Masahiro Yamashita、Hitoshi Miyasaka、Ken-ichi Sugiura、Harutaka Watanabe、Daichi Suzuki、Hiroshi Ito、Shin-ichi Kuroda

  DOI：10.1246/cl.2006.368

  日期：2006.4

  Two charge-transfer salts (DMET)3[Cr(isoq)2(NCS)4] (1) and (DMET)3[Cr(phen)(NCS)4]·CH3CN (2) have been prepared and characterized. The single-crystal X-ray crystallography revealed that the structures of both salts consist of segregated columns of DMET and metal complex anions. The magnetic and transport properties have shown that these salts are paramagnetic semiconductors.

  两种电荷转移盐（DMET）3[Cr（isoq）2（NCS）4]（1）和（DMET）3[Cr（苯）（NCS）4]·CH3CN（2）已经制备并表征。单晶X射线晶体学显示，两种盐的结构均由DMET和金属络合阴离子的分离柱组成。磁性和传输特性表明，这些盐是顺磁性半导体。
• Tetramerized Structure of (DMET)₂ReO₄and Its Apparent Metallic Behavior in Resistivity
  作者：Kazuya Saito、Yoshimitsu Ishikawa、Masayoshi Ishibashi、Koichi Kikuchi、Keiji Kobayashi、Isao Ikemoto

  DOI：10.1246/bcsj.63.1865

  日期：1990.7

  The crystal structure of (DMET)2ReO4 (DMET: 5,6-dihydro-2-(4,5-dimethyl-1,3-diselenol-2-ylidene)dithiolo[4,5-b][1,4]dithiin) was determined, and its resisitivity and thermoelectric power were measured. Crystal data; (C10H10S4Se2)2·ReO4, Mr=1082.88, triclinic, P\bar1, a=6.715(1) Å, b=14.486(2) Å, c=15.867(2) Å, α=101.95(4)°, β=90.05(1)°, γ=78.43(1)°, V=1478.2(3) Å3, Z=2, Dx=2.43 Mg m−3, μ(Mo Kα)=9.62 mm−1, F(000)=1022, T=297 K, R=0.074 for 4391 reflections. The crystal has columnar structure. In the column, a large degree of tetramerization is observed. The resistivity under the normal pressure has metallic temperature dependence above ca. 295 K. The thermoelectric power is essentially constant above 200 K and no anomaly was detected around 295 K. The apparent metallic behavior was attributed to the small activation energy (band-gap) and the temperature dependence of the carrier mobility.

  已测定（DMET）2ReO4（DMET：5,6-二氢-2-(4,5-二甲基-1,3-二硒醇-2-亚基)二硫醇[4,5-b][1,4]二硫杂环戊烯）的水晶结构，并测量了其电阻率和热电功率。晶体数据；（C10H10S4Se2）2·ReO4，Mr=1082.88，三斜晶，P\bar1，a=6.715(1) Å，b=14.486(2) Å，c=15.867(2) Å，α=101.95(4)°，β=90.05(1)°，γ=78.43(1)°，V=1478.2(3) Å3，Z=2，Dx=2.43 Mg m−3，μ(Mo Kα)=9.62 mm−1，F(000)=1022，T=297 K，R=0.074，4391个反射。该晶体具有柱状结构。在柱状结构中，观察到大量四聚现象。在常压下，电阻率在约295 K
• Noncoupling Synthesis of Unsymmetrical Tetrathiafulvalene Derivatives. Dihydrotetrathiafulvalenes as New Electron Donors
  作者：Jun-ichi Yamada、Yoshiki Amano、Satoshi Takasaki、Rie Nakanishi、Kaoru Matsumoto、Shyuji Satoki、Hiroyuki Anzai

  DOI：10.1021/ja00108a040

  日期：1995.1