5-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one | 64407-82-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one
• 英文别名: 2-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-[1,3]dithiolo[4,5-d][1,3]dithiol-5-one
• CAS: 64407-82-5
• 化学式: C₉H₆OS₈
• 分子量: 386.674
• InChiKey: IZGOFNBRKFMRNB-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C (decomp)
• 沸点：
  451.6±55.0 °C(predicted)
• 密度：
  1.84±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  220
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one 在 亚磷酸三乙酯 作用下， 以45%的产率得到5,5'-Bis-(4,5-bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-[2,2']bi[[1,3]dithiolo[4,5-d][1,3]dithiolylidene]
  参考文献：
  名称：

  Synthesis and Properties of Alkylthio-Substituted Tris-Fused Tetrathiafulvalenes

  摘要：

  已合成了几个标题捐赠者的衍生物（1a-c）。四（己基硫）衍生物1c的循环伏安图显示了三对双电子转移波。1a-c的碘络合物在室温下显示出相对较高的电导率，为10-1-101 S cm-1。

  DOI：

  10.1246/cl.1996.43
• 作为产物：
  描述：

  [4-[[5-[(4-Acetyloxyphenyl)methylsulfanyl]-2-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-dithiol-4-yl]sulfanylmethyl]phenyl] acetate 在 三光气 、 四丁基溴化铵 、 sodium methylate 、 zinc(II) chloride 作用下， 生成 5-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one
  参考文献：
  名称：

  Methylthio Substituted 2,5-Bis(1′,3′-dithiol-2′-ylidene)-1,3,4,6-tetrathiapentalene. A Bis-Fused Tetrathiafulvalene

  摘要：

  介绍了标题化合物 (1) 的合成、X 射线晶体分析法确定的分子结构以及循环伏安法研究的电化学特性。通过电化学氧化法制备了 1 的几种阳离子基盐，并介绍了它们的电学性质。

  DOI：

  10.1246/cl.1992.2321

文献信息

• Cyclohexylenedithio Annelated Bis-Fused TTF Donors and Their Conducting Salts
  作者：Minoru Ashizawa、Masanobu Aragaki、Takehiko Mori、Yohji Misaki、Tokio Yamabe

  DOI：10.1246/cl.1997.649

  日期：1997.7

  Bis-fused TTF(tetrathiafulvalene) derivatives with a cyclohexane ring 1a-c have been synthesized. One of their radical-cation salts (1b)2Au(CN)2 exhibits high conductivity σrt=160 Scm−1 and is metallic down to 120 K. Its structure consists of weakly dimerized columns with relatively small intercolumnar interactions.

  具有环己烷环的双联四硫富瓦烯 (TTF) 衍生物 1a-c 已被合成。它们其中一种自由基阳离子盐 (1b)2Au(CN)2 表现出高导电性 σrt=160 Scm−1，并且在 120 K 以下仍保持金属性。其结构由弱二聚化的柱组成，柱间相互作用相对较小。
• Bis(methylthio) Substituted Unsymmetrical 2,5-Bis(1′,3′-dithiol-2′-ylidene)-1,3,4,6-tetrathiapentalenes
  作者：Yohji Misaki、Hiroyuki Nishikawa、Tokio Yamabe、Takehiko Mori、Hiroo Inokuchi、Hatsumi Mori、Shoji Tanaka

  DOI：10.1246/cl.1993.729

  日期：1993.4

  The title compounds (2) were synthesized as the donor components for organic conductors, and preparation and electrical properties of their cation radical salts were investigated. Among various cation radical salts obtained so far, AsF6 salt of ethylenedithio-2 and SbF6 salt of ethylenedioxy-2 showed metallic temperature dependence of conductivities down to 0.6 K.

  我们合成了标题化合物 (2) 作为有机导体的供体成分，并研究了其阳离子自由基盐的制备和电学特性。在目前获得的各种阳离子自由基盐中，亚乙二硫基-2 的 AsF6 盐和亚乙二氧基-2 的 SbF6 盐的电导率在 0.6 K 以下显示出金属温度依赖性。
• Fused Tetrathiafulvalene and Benzoquinone Triads: Organic Positive‐Electrode Materials Based on a Dual Redox System
  作者：Yohji Misaki、Shigenobu Noda、Minami Kato、Tomokazu Yamauchi、Toko Oshima、Aya Yoshimura、Takashi Shirahata、Masaru Yao

  DOI：10.1002/cssc.202000178

  日期：2020.5.8

  Fused donor-acceptor triads composed of two tetrathiafulvalenes (TTFs) and benzoquinone (BQ; 1) or naphthoquinone (NQ; 2) were successfully synthesized. X-ray structure analysis of the bis(n-butylthio) derivative revealed that the molecules are stacked in a head-to-tail manner. The bis(n-hexylthio)-1 exhibited six-pairs of one-electron transfer waves in the cyclic voltammogram, corresponding to the

  成功合成了由两个四硫富瓦烯（TTF）和苯醌（BQ; 1）或萘醌（NQ; 2）组成的熔融供体-受体三联体。对双（正丁硫基）衍生物的X射线结构分析表明，分子以头对尾的方式堆叠。双（正己硫基）-1在循环伏安图中显示六对单电子转移波，对应于从-2到+4的还原态和氧化态的形成。1和2的未取代和双（甲硫基）衍生物是可再充电电池正极中的活性材料，其中一些具有超过800 mWh g-1的能量密度。双（甲硫基）-2还用作可充电钠离子电池的正极材料。
• New π -Donor Molecules with a Pyrazino Group and their Conducting Salts
  作者：G. C. Papavassiliou、Yohji Misaki、Kazuko Takahashi、Jun-ichi Yamada、G. A. Mousdis、Takashi Sharahata、Toshihiro Ise

  DOI：10.1515/znb-2001-0313

  日期：2001.3.1

  The preparation and characterization of some π-donors with a pyrazine-edge-group as well as with tetrathiapentalene-, thiophene-, and dihydrobenzoselenophene-spacer-groups are de­ scribed. Some of these donors give conducting charge transfer complexes with TCNQ and/or cation radical salts with I₃ ^-, BF₄ ^-and PF₆ ^-as counter anions.

  摘要：本文描述了一些具有吡嗪边基团、四硫代戊二烯、噻吩和二氢苯并硒的空穴传输分子的制备和表征。其中一些给出与TCNQ形成导电的电荷转移复合物，或与I₃ ^-、BF₄ ^-和PF₆ ^-等阳离子盐形成的阳离子基盐。
• Two-Dimensional Brickblock Arrangement in Bis-Fused Tetrathiafulvalene Semiconductors
  作者：Takeshi Terauchi、Satoshi Sumi、Yuka Kobayashi、Yoshitaka Matsushita、Akira Sato

  DOI：10.1021/cg401883g

  日期：2014.3.5

  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.