dimethyl 2-{5-(1,3-dithiol-2-ylidene)-[1,3]dithiolo[4,5-d]-[1,3]dithiol-2-ylidene}-1,3-dithiole-4,5-dicarboxylate | 152588-54-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 2-{5-(1,3-dithiol-2-ylidene)-[1,3]dithiolo[4,5-d]-[1,3]dithiol-2-ylidene}-1,3-dithiole-4,5-dicarboxylate
• 英文别名: Dimethyl 2-[2-(1,3-dithiol-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-5-ylidene]-1,3-dithiole-4,5-dicarboxylate
• CAS: 152588-54-0
• 化学式: C₁₄H₈O₄S₈
• 分子量: 496.743
• InChiKey: PSHXGTDJKNSDRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  255
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  dimethyl 2-{5-(1,3-dithiol-2-ylidene)-[1,3]dithiolo[4,5-d]-[1,3]dithiol-2-ylidene}-1,3-dithiole-4,5-dicarboxylate 在 lithium bromide monohydrate 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 2.0h， 以84%的产率得到[1,3]二噻唑并[4,5-d]-1,3-二噻唑,2,5-二(1,3-二硫醇-2-亚基)-
  参考文献：
  名称：

  一元和二元羧酸双稠合四硫富瓦烯的合成

  摘要：

  具有单和二羧酸，2- {5-（1,3-二硫醇-2-亚烷基）- [1,3]二硫代[4,5- d ] [1,3]二硫醇-2-的双融合四硫富瓦烯亚基} -1,3-二硫代-4-羧酸（1）和2- {5-（1,3-二硫代-2-亚烷基）-[1,3]二硫代[4,5- d ] [1，合成了3]二硫醇-2-亚烷基} -1，3-二硫醇-4，5-二羧酸（2）。从其1和2的电子吸收光谱和使用密度泛函计算来检查其电子结构。

  DOI：

  10.1016/j.tetlet.2012.04.064
• 作为产物：
  描述：

  4,5-bis(2-cyanoethylsulfanyl)tetrathiafulvalene 在 sodium methylate 、 三甲氧基磷 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 35.5h， 生成 dimethyl 2-{5-(1,3-dithiol-2-ylidene)-[1,3]dithiolo[4,5-d]-[1,3]dithiol-2-ylidene}-1,3-dithiole-4,5-dicarboxylate
  参考文献：
  名称：

  Two-Dimensional Brickblock Arrangement in Bis-Fused Tetrathiafulvalene Semiconductors

  摘要：

  Molecular packing arrangement is a very important factor in the charge carrier mobility of organic semiconductors, but its rational design has not been established as yet. Two-dimensional (2D) lamellar packing is an advantageous arrangement for high charge mobility, but few examples have been reported thus far. Herein we show crystal structures and the electronic properties of newly designed bis-fused tetrathiafulvalene (TTF) semiconductors with hetero substituent groups with distinct electronic effects. Unprecedented 2D lamellar alignment is achieved in a single crystal, where the bis-fused TTF rings interact three dimensionally with face-to-face and side-by-side intermolecular S center dot center dot center dot S contacts up to a total of 20 sites per pi molecule and form graphitelike "brickblock" structure. The charge mobility of a single crystal is as high as 0.78 cm(2) V-1 s(-1). Systematic investigations of the semiconductors reveal a key role of intramolecular S center dot center dot center dot O interaction between a bis-fused TTF ring and a methoxycarbonyl group in controlling efficient arrangement, leading to high mobility.

  DOI：

  10.1021/cg401883g

文献信息

• 2,5-Bis(1′,3′-dithiol-2′-ylidene)-1,3,4,6-tetrathiapentalene and Its Related Unsymmetrical Donors
  作者：Yohji Misaki、Toshitaka Matsui、Kazuya Kawakami、Hiroyuki Nishikawa、Tokio Yamabe、Motoo Shiro

  DOI：10.1246/cl.1993.1337

  日期：1993.8

  The title compound (1a) and its related unsymmetrical derivatives were prepared as new donors for organic conductors, and electrochemical properties and crystal structure of 1a were investigated. Several charge-transfer complexes and cation radical salts using them showed metallic temperature dependence of conductivity down to ca. 100 K.

  制备了标题化合物(1a)及其相关的不对称衍生物作为有机导体的新供体，并研究了1a的电化学性质和晶体结构。使用它们的几种电荷转移复合物和阳离子自由基盐显示出金属温度依赖性的电导率低至约 。100K。