4,5-ethylenedithio-1,3-diseleno-2-one | 88682-23-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5-ethylenedithio-1,3-diseleno-2-one
• 英文别名: 4,5-ethylenedithio-1,3-diselenol-2-one；4,5-(ethylenedithio)-1,3-diselenole-2-one；5,6-Dihydro-[1,3]diselenolo[4,5-b][1,4]dithiin-2-one
• CAS: 88682-23-9
• 化学式: C₅H₄OS₂Se₂
• 分子量: 302.138
• InChiKey: XSINCHAFIBPKFD-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  10
• 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：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-ethylenedithio-1,3-diseleno-2-one 在 亚磷酸三乙酯 作用下， 以50%的产率得到Bis(ethylenedithio)tetraselenafulvalene
  参考文献：
  名称：

  有机无机杂化室温金属性的分子磁体及其制备 方法

  摘要：

  本发明公开了一种有机无机杂化室温金属性的分子磁体及其制备方法。本发明提供的室温金属性的分子磁体的分子式为：BETS3[Cu2(C2O4)3]B2，其中，BETS表示二硫代二乙撑基四硒富瓦烯，B表示醇类化合物；本发明提供的金属性的分子磁体的制备方法，包括如下步骤：以所述醇类化合物为电解质溶液，草酸铜的铵盐和BETS在电化学池中进行电化学反应，在阳极上得到所述室温金属性的分子磁体。本发明提供的室温金属性的分子磁体的制备方法，从有机π电子体系和Jahn-Teller畸变的磁性阴离子出发，在有机溶剂体系制备有机无机杂化室温金属性的分子磁体单晶；本发明提供的有机无机杂化室温金属性的分子磁体的晶体质量好，且产物单一，得率高。

  公开号：

  CN103864820B

文献信息

• Synthesis, structures and electrical properties of the charge-transfer salts of 4,5-ethylenedithio-4′,5′-(2-oxatrimethylenedithio)diselenadithiafulvalene (EOST) with linear anions [I–3, IBr–2, ICl–2, I₂Br^–, AuBr–2, Au(CN)–2]
  作者：Toshio Naito、Akiko Tateno、Takashi Udagawa、Hayao Kobayashi、Reizo Kato、Akiko Kobayashi、Takashi Nogami

  DOI：10.1039/ft9949000763

  日期：——

  An unsymmetrical donor 4,5-ethylenedithio-4′,5′-(2-oxatrimethylenedithio)-diselenadithiafulvalene (EOST)† has been synthesized. Single crystals of some charge-transfer salts of EOST have been prepared electrochemically. The crystal structures of EOST and its charge-transfer salts were analysed by X-ray crystallography. The dc resistivities were measured on the single crystals. Eight of the salts with linear anions [(EOST)2I3, α-(EOST)2IBr2, β-type IBr2 salt, (EOST)2ICl2, (EOST)2I2Br, α- and β-type AuBr2 salts and Au(CN)2 salt] retained their metallic conductivity down to low temperatures (⩽ 35 K) and some were found to be isostructural. The overlap integrals of some salts and the tight-binding band was examined for (EOST)2I3. The result suggested that it has a quasi-one-dimensional electronic structure and that EOST molecules interact most strongly in a side-by-side direction. The crystal and electronic structures of (EOST)2I3 are discussed by comparison with the isostructural compound (EOTT)2IBr2[EOTT: 4,5-ethylenedithio-4′,5′-(2-oxatrimethylenedithio) tetrathiafulvalene].

  合成了非对称给体4,5-乙撑二硫-4',5'-(2-恶二甲撑二硫)-二硒二硫富瓦烯(EOST)。用化学法制备了EOST的部分电荷转移盐单晶。用X射线晶体学方法分析了EOST及其电荷转移盐的晶体结构。在单晶上测定了电阻率。8种具有线型阴离子的盐[(EOST)_2I_3,α-(EOST)_2IBr_2,β-型IBr_2盐,(EOST)_2ICl_2,(EOST)_2I_2Br,α-型和β·型AuBr_2盐和Au(CN)_2盐]在低温(≤35K)下保持了金属导电性,某些盐是同构的。对(EOST)_2I_3考查了某些盐的重叠积分和紧束缚能带,结果表明它具有准一维电子结构。EOST分子之间在肩并肩方向上有最强的相互作用。通过与同构化合物(EOTT)_2IBr_2[EOTT:4,5-乙撑二硫-4',5'-(2-恶二甲撑二硫)四硫富瓦烯]相比较,讨论了(EOST)_2I_3的晶体结构和电子结构。
• Unexpected Formation of <i>ortho</i>-Benzoquinone-fused Tetraselenafulvalene (TSF): Synthesis, Structures, and Properties of a Novel TSF-based Donor–Acceptor Dyad
  作者：Akira Ueda、Hiromichi Kamo、Hatsumi Mori

  DOI：10.1246/cl.150701

  日期：2015.11.5

  Electrochemical oxidation of a catechol-fused tetraselenafulvalene (TSF) derivative unexpectedly gave its ortho-benzoquinone analogue, in contrast to the tetrathiafulvalene (TTF) system that afforded a hydrogen-bonded organic conductor. The obtained donor–acceptor dyad showed amphoteric redox character, a small HOMO–LUMO gap, effective intermolecular interactions, and NIR absorption.

  一种儿茶酚融合的四硒富瓦烯（TSF）衍生物的电化学氧化反应出乎意料地得到了其邻苯醌类似物，这与四硫富瓦烯（TTF）体系形成氢键有机导电体的反应不同。获得的供体-受体二聚体显示出两性氧化还原特性、较小的最高占据分子轨道与最低未占据分子轨道间能隙、有效的分子间相互作用以及近红外吸收特性。
• Stable molecular metals based on a novel unsymmetrical diselenadithiafulvalene
  作者：Shuji Aonuma、Yoshinori Okano、Hiroshi Sawa、Reizo Kato、Hayao Kobayashi

  DOI：10.1039/c39920001193

  日期：——

  Novel unsymmetrical π-electron donors have been synthesized and electrical conductivities of their radical cation salts have been studied: among them 4,5-ethylenedithio-4′,5′-(isopropylidenemethylenedithio)diselenadithiafulvalene salts are all metallic down to 4.2 K, and exhibit two-dimensional nature in the anisotropy of the conductivity.

  新型不对称π电子供体已被合成，并研究了其自由基阳离子盐的电导率：其中，4,5-乙烯二硫-4′,5′-(异丙基亚甲基二硫)二硒二硫富瓦烯盐在4.2 K下均呈现金属特性，并在电导率的各向异性中展现出二维特性。
• Efficient synthesis of brominated tetrathiafulvalene (TTF) derivatives: solid-state structure and electrochemical behaviour
  作者：Antonio Alberola、Rebecca J. Collis、Felipe García、Ruth E. Howard

  DOI：10.1016/j.tet.2006.06.006

  日期：2006.8

  An efficient synthesis is reported for 4,5-dibromo-[1,3]dithiole-2-thione (1) and 4-bromo-1,3-dithiole-2-thione (7) by bromination of lithiated vinylene trithiocarbonate. Compound 1 acts as a convenient precursor to a number of asymmetric electron donors. This is exemplified by the formation of 4,5-dibromo-4′,5′-bis(2′-cyanoethylsulfanyl)TTF (3) by cross-coupling methodology and subsequent conversion

  据报道，通过溴化锂化的亚乙烯基三硫代碳酸酯可以有效合成4,5-二溴-[1,3]二硫代-2-硫酮（1）和4-溴-1,3-二硫代-2-硫酮（7）。化合物1充当许多不对称电子供体的便利前体。这通过交叉偶联方法形成4,5-二溴-4'，5'-双（2'-氰基乙基硫基）TTF（3）并随后转化为4,5-二溴-4'，5'来举例说明-乙烯二硫代TTF（4）通过与氢氧化铯和1，2-二溴乙烷反应。新的供体4,5-二溴4'，5'-亚乙基二硫代二硒二氮富瓦烯（5）是通过将1和4,5-亚乙基二硫-1,3-二硒酚-2-一（6）。报告了3和5的X射线结构。
• Synthesis and properties of hetero-halogenated TTFsElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/ob/b3/b310822h/
  作者：Rie Suizu、Tatsuro Imakubo

  DOI：10.1039/b310822h

  日期：——

  Novel hetero-halogenated TTFs containing both chlorine and iodine atoms were prepared and their unique characters based on the halogen atoms were examined.

  制备了新型含有氯和碘原子的异卤化TTFs，并对其基于卤素原子的独特特性进行了研究。