4,5-bis(methylseleno)-1,3-dithiole-2-thione | 128346-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4,5-bis(methylseleno)-1,3-dithiole-2-thione
• 英文别名: 4,5-Bis(methylselanyl)-2H-1,3-dithiole-2-thione；4,5-bis(methylselanyl)-1,3-dithiole-2-thione
• CAS: 128346-96-3
• 化学式: C₅H₆S₃Se₂
• 分子量: 320.221
• InChiKey: ARLMUWFHMPUFMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-bis(methylseleno)-1,3-dithiole-2-thione 在 cesium hydroxide 、 三甲氧基磷 、 亚磷酸三乙酯 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 5.0h， 生成 2,5-bis[4,5-bis(methylseleno)-1,3-dithiol-2-ylidene]-1,3,4,6-tetrathiapentalene
  参考文献：
  名称：

  Novel One-Dimensional Organic Conductor Based on Selenium-Containing Bis-Fused Tetrathiafulvalene Derivative, (TSM-TTP)(I₃)_5/3

  摘要：

  一种新型含硒双融合四硫杂戊烯供体 TSM-TTP（2,5-双[4,5-双（甲基硒）-1,3-二硫醇-2-亚基]-1,3,4,6-四硫杂戊烯）形成了 3 : 5 三碘盐 (TSM-TTP)(I3)5/3。这种盐具有均匀的一维供体柱，与硫类似物的相应复合物结构相同。这种化合物具有很高的导电性，室温下为 200 S cm-1，并在 20 K 左右发生金属-绝缘体转变。

  DOI：

  10.1246/bcsj.71.1321
• 作为产物：
  描述：

  三硫代碳酸亚乙烯酯 、 碘甲烷 在 lithium diisopropyl amide 、 selenium 作用下， 生成 4,5-bis(methylseleno)-1,3-dithiole-2-thione
  参考文献：
  名称：

  Novel One-Dimensional Organic Conductor Based on Selenium-Containing Bis-Fused Tetrathiafulvalene Derivative, (TSM-TTP)(I₃)_5/3

  摘要：

  一种新型含硒双融合四硫杂戊烯供体 TSM-TTP（2,5-双[4,5-双（甲基硒）-1,3-二硫醇-2-亚基]-1,3,4,6-四硫杂戊烯）形成了 3 : 5 三碘盐 (TSM-TTP)(I3)5/3。这种盐具有均匀的一维供体柱，与硫类似物的相应复合物结构相同。这种化合物具有很高的导电性，室温下为 200 S cm-1，并在 20 K 左右发生金属-绝缘体转变。

  DOI：

  10.1246/bcsj.71.1321

文献信息

• Conducting Salts Composed of Selenium Analogues of TMET-TTP
  作者：Takehiko Mori、Minoru Ashizawa、Masanobu Aragaki、Kyoji Murata、Yohji Misaki、Kazuyoshi Tanaka

  DOI：10.1246/cl.1998.253

  日期：1998.3

  Selenium analogues of TMET-TTP (2-(4,5-bisthiomethyl-1,3-dithiol-2-ylidene)-5-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene) 1b-d have been synthesized. The iodine salt (1b)4I3 exhibits moderately high conductivity (σrt=13S cm−1) with semiconducting temperature dependence, and the donor arrangement is θ-type. The present θ-type salt as well as TMET-TTP salts is located at the insulating limit in the universal phase diagram of θ-phases.

  TMET-TTP（2-(4,5-双硫甲基-1,3-二硫杂环-2-亚基)-5-(4,5-乙烯基二硫-1,3-二硫杂环-2-亚基)-1,3,4,6-四硫杂五环烯）的硒类似物1b-d已被合成。碘盐（1b）4I3表现出中等高度的导电性（σrt=13S cm−1），具有半导体温度依赖性，且给体排列为θ型。目前的θ型盐以及TMET-TTP盐位于θ相的普遍相图中的绝缘极限处。
• A Novel Organic Conductor with Two-Dimensional Molecular Array by the “Edge-to-Edge” Donor Interaction
  作者：Kazuyuki Takahashi、Takashi Nakayashiki、Masateru Taniguchi、Yohji Misaki、Kazuyoshi Tanaka

  DOI：10.1246/cl.2001.162

  日期：2001.2

  The title donor, where SM-PDT is 2-[4,5-bis(selenomethyl)-1,3-dithiol-2-ylidene]-5-(pyran-4-ylidene)-1,3,4,6-tetrathiapentalene, formed semiconducting 1:1 salts with various anions. The crystal structure analysis of (SM-PDT)PF6(PhCl)x has revealed that an edge-to-edge chalcogen interaction gave two-dimensional sheet-like structure.

  标题供体 SM-PDT 是 2-[4,5-双（硒甲基）-1,3-二硫醇-2-亚基]-5-（吡喃-4-亚基）-1,3,4,6-四硫杂戊烯，与各种阴离子形成 1:1 的半导体盐。(SM-PDT)PF6(PhCl)x 的晶体结构分析表明，边对边的查尔基因相互作用产生了二维片状结构。
• New vinylogous tetrathiafulvalene .pi.-electron donors with peripheral alkylseleno substitution
  作者：Martin R. Bryce、Malcolm A. Coffin、William Clegg

  DOI：10.1021/jo00032a018

  日期：1992.3

  Efficient syntheses are described for five new vinylogous pi-electron donors, viz. 5, 6, and 8-10, which are related to bis(ethylenediseleno)tetrathiafulvalene (3): symmetrical and unsymmetrical systems, containing mixed alkylseleno and alkylthio groups, have been obtained. The solution electrochemical redox properties, studied by cyclic voltammetry, establish that these molecules undergo two, single-electron, oxidations at low potentials. The single-crystal X-ray structure of 4,5-bis(methylseleno)-4',5'-bis(methylthio)-2,2'-ethanediylidene(1,3-dithiole) (6) is reported. Semiconducting complexes of the new donors with tetracyano-p-quinodimethane have been obtained.
• New TTP Donors Containing Chalcogenopyran-4-ylidene: Preparation, Structures, and Electrical Properties
  作者：Kazuyuki Takahashi、Takashi Nakayashi、Yohji Misaki、Kazuyoshi Tanaka

  DOI：10.1080/10587250210766

  日期：2002.1.1

  Several TM-PDT analogous donors, where TM-PDT is 2-[4,5-bis(thiomethyl)-1,3-dithiol-2-ylidene]-5-(pyran-4-ylidene)-1,3,4,6-tetrathiapentalene, have been prepared. Cyclic voltammetry demonstrated that chalcogen atom exchange at chalcogenopyran moiety in donors strongly influenced their redox potentials. Electrical conductivity of all their salts showed a semiconducting behavior with relatively small activation energy. Crystal structure of (SM-PDT)(TCNQ), where TM-PDT is 2-[4,5-bis(selenomethyl)-1,3-dithiol-2-ylidene]-5-(pyran-4-ylidene)-1,3,4,6-tetrathiapentalene, has been revealed to compose of the D-A type mixed stacks.