4,5-diiodo-[1,3]diselenol-2-one | 646037-49-2

• 分子结构分类: 有机化合物
• 英文名称: 4,5-diiodo-[1,3]diselenol-2-one
• 英文别名: 4,5-diiodo-1,3-diselenole-2-one；4,5-Diiodo-1,3-diselenol-2-one
• CAS: 646037-49-2
• 化学式: C₃I₂OSe₂
• 分子量: 463.761
• InChiKey: CMQYUCRKGVWCRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-diiodo-[1,3]diselenol-2-one 在 亚磷酸三乙酯 作用下， 以 甲苯 为溶剂， 以89%的产率得到4,5,4',5'-Tetraiodo-[2,2']bi[[1,3]diselenolylidene]
  参考文献：
  名称：

  [1,3]二硒烯-2-硫酮的无CSe2合成及其在碘化四硒富勒烯（TSeFs）合成中的应用。

  摘要：

  我们开发了一种新的不含CSe2的方案，用于合成[1,3]二硒烯-2-硫酮，并将其转化为四硒富勒烯衍生物，而没有任何硒-硫交换副反应。

  DOI：

  10.1039/b304136k
• 作为产物：
  描述：

  4,5-diiodo[1,3]diselenole-2-thione 在 mercury(II) diacetate 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 以97%的产率得到4,5-diiodo-[1,3]diselenol-2-one
  参考文献：
  名称：

  [1,3]二硒烯-2-硫酮的无CSe2合成及其在碘化四硒富勒烯（TSeFs）合成中的应用。

  摘要：

  我们开发了一种新的不含CSe2的方案，用于合成[1,3]二硒烯-2-硫酮，并将其转化为四硒富勒烯衍生物，而没有任何硒-硫交换副反应。

  DOI：

  10.1039/b304136k

文献信息

• Synthesis of novel selenium-containing donors as selenium analogues of diiodo(ethylenedithio)diselenadithiafulvalene (DIETS)Electronic supplementary information (ESI) available: Experimental details. See http://www.rsc.org/suppdata/ob/b4/b406092j/
  作者：Takashi Shirahata、Tatsuro Imakubo

  DOI：10.1039/b406092j

  日期：——

  Novel selenium analogues of diiodo(ethylenedithio)diselenadithiafulvalene (DIETS) have been successfully derived from 1,3-diselenole-2-thione, which could be synthesized without the use of the highly toxic reagent CSe2.

  新型硒类似物二碘(乙撑二硫)二硒二硫富瓦烯 (DIETS) 已成功从 1,3-二硒醇-2-硫酮衍生而来，无需使用剧毒试剂 CSe2 即可合成。
• Hybrid Organic/Inorganic Supramolecular Conductors D ₂ [Au(CN) ₄ ] [D = Diiodo(ethylenedichalcogeno)tetrachalcogenofulvalene], Including a New Ambient Pressure Superconductor
  作者：Tatsuro Imakubo、Takashi Shirahata、Megumi Kibune、Hiroko Yoshino

  DOI：10.1002/ejic.200700530

  日期：2007.10

  highly toxic reagent CSe2, and their Au(CN)4 salts have been prepared by electrochemical oxidation. Characteristic I···N iodine bonds are constructed in all crystals, and their packing motifs are classified into two groups by the difference in the space group symmetry. The salt of DIEDSS crystallizes in the monoclinic C2/c space group and a novel helical supramolecular architecture is constructed by the

  五种二碘（亚乙基二硫属）四硫属元素富瓦烯，DIEDSS 2-(5,6-dihydro[1,3]diselenolo[4,5-b][1,4]diselenin-2-ylidene)-4,5-diiodo-1， 3-二硫醇}, DIET-STF 2-(4,5-diiodo-1,3-diselenol-2-ylidene)-5,6-dihydro[1,3]dithiolo[4,5-b][1, 4]dithiine}, DIEDS-STF 2-(4,5-diiodo-1,3-diselenol-2-ylidene)-5,6-dihydro[1,4]diselenino[2,3-d][1, 3]dithiole}, DIETSe 2-(4,5-diiodo-1,3-diselenol-2-ylidene)-5,6-dihydro[1,3]diselenolo[4,5-b][1,4] dithiine}
• Supramolecular organic conductors based on diiodo-TTFs and spherical halide ion X⁻(X = Cl, Br)
  作者：Tatsuro Imakubo、Takashi Shirahata、Katel Hervé、Lahcène Ouahab

  DOI：10.1039/b512036e

  日期：——

  Novel organic conductors based on four diiodotetrathiafulvalene derivatives, DIET (2-(4,5-diiodo-[1,3]dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiine), DIETSe (2-(4,5-diiodo-[1,3]diselenol-2-ylidene)-5,6-dihydro-[1,3]diselenolo[4,5-b][1,4]dithiine), DIEDO (2-(4,5-diiodo-[1,3]dithiol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxine) and DIEDO-STF (2-(4,5-diiodo-[1,3]diselenol-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dioxine) have been prepared using spherical halide ion X− (X = Cl, Br) as the counter anion. Crystal structure analyses have revealed that all halide salts contain supramolecular structures tailored by the strong I⋯X iodine bond and their molecular arrangement depends on the combination of the group 16 elements included in the donor molecule. The temperature dependence of the electrical resistivity of (DIET)2X(H2O)2 is metallic down to 4.2 K, and they have ideally two-dimensional Fermi surfaces within the donor layer. (DIETSe)2X(CH2Cl2) salts show small temperature dependence of the resistivity down to low temperatures and their “double column” structure is dominated by the Y-shaped architecture composed of the halide ion and the crystalline solvent. On the other hand, (DIEDO)2X and (DIEDO-STF)2X are semiconducting from room temperature. They have another type of “double column” structure, i.e. the adjacent donor molecules along the side-by-side direction are solid-crossing and two types of column are included in the donor layer. The packing motifs of the halide salts based on the oxygen-substituted donor molecules are the same but their electronic states are sensitive to changes in the chalcogen atoms on the inner TTF skeleton.

  X(H2O)2盐的电阻率在4.2 K以下呈金属性，在供体层内具有理想的二维费米表面。(DIETSe)2X(CH2Cl2)盐的电阻率在低温下呈现较小的温度依赖性，其“双柱”结构主要由卤化物离子和结晶溶剂组成的Y形结构主导。另一方面，(DIEDO)2X( )2盐的电阻率在4.2 K以下呈金属性，在供体层内具有理想的二维费米表面。(DIETSe)2X( )盐的电阻率在低温下呈现较小的温度依赖性，其“双柱”结构主要由卤化物离子和结晶溶剂组成的Y形结构主导。
• Hexagonal supramolecular organic conductors based on diiodo(pyrazino)tetraselenafulvalene: high yield recovery of the neutral π-donor by a simple chemical reaction
  作者：Tatsuro Imakubo、Megumi Kibune、Hiroko Yoshino、Takashi Shirahata、Kenji Yoza

  DOI：10.1039/b611010j

  日期：——

  Conducting cation radical salts based on a pyrazine-fused iodine-bonded π-donor diiodo(pyrazino)tetraselenafulvalene (DIPSe) and octahedral anions AF6 (A = P, As, Sb) have been prepared by electrochemical oxidation. X-Ray structure analysis revealed that these three salts are isostructural and crystallize in the hexagonal P63/mcm space group. There is a strong and directional I⋯N iodine bond among the donor molecules, which is 18–19% shorter than the sum of the van der Waals radii. The hexagonal lattice is filled with the equilateral triangles of the donor molecules tailored by the I⋯N iodine bond and there are also two types of supramolecular channels including the counter anion and the crystalline solvent. The room temperature resistivities of these three salts are in the order of 10−2 Ω cm with metallic behaviour and they show a gentle upturn at around 250 K. In addition to the high-symmetrical crystal structure and the metallic conductivity, high yield recovery of the neutral π-donor from the cation radical salts has been accomplished by a simple chemical reaction. In situ1H-NMR monitoring of the reaction process indicates that the DIPSe cation radical was reduced by water and the characteristic supramolecular channels, which allow water molecules to access the cation radicals deep in the crystal, are essential for smooth progress of the recovery process.

  基于吡嗪-融合碘键的Β-供体二碘（吡嗪）四硒烯富瓦烯（DIPSe）和八面体阴离子AF6（A = P、As、Sb）的阳离子自由基盐通过电化学氧化制备而成。X射线结构分析显示，这三种盐具有相同的结构，并以六方P63/mcm空间群结晶。供体分子之间存在强定向I➔N碘键，其长度比范德华半径之和短18-19%。六方晶格中充满了由I➔N碘键形成的供体分子的等边三角形，还有两种超分子通道，包括反离子和结晶溶剂。这三种盐的室温电阻率约为10⁻² Å·cm，具有金属特性，并在250 K左右出现温和上升。除了高对称晶体结构和金属导电性外，通过简单的化学反应，还可以从阳离子自由基盐中回收大量中性Β-供体。反应过程的原位1H-NMR监测表明，DIPSe阳离子自由基被水还原，而允许水分子进入晶体深处的阳离子自由基的典型超分子通道对于回收过程的顺利进行至关重要。