2,3,6,7,10,11-hexa(methylthio)triphenylene | 206876-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,3,6,7,10,11-hexa(methylthio)triphenylene
• 英文别名: 2,3,6,7,10,11-Hexakis(methylthio)triphenylene；2,3,6,7,10,11-hexakis(methylsulfanyl)triphenylene
• CAS: 206876-04-2
• 化学式: C₂₄H₂₄S₆
• 分子量: 504.851
• InChiKey: YHVUINDSSICLLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,6,7,10,11-hexa(methylthio)triphenylene 在 lithium 作用下， 以 氨 为溶剂， 反应 3.5h， 以91%的产率得到六巯基三亚苯
  参考文献：
  名称：

  π-Conjugated Trinuclear Group-9 Metalladithiolenes with a Triphenylene Backbone

  摘要：

  Previously, we synthesized pi-conjugated trinuclear metalladithiolene complexes based on benzenehexathiol (j. Chem. Soc., Dalton Trans. 1998, 2641; Dalton Trans. 2009, 1939; Inorg. Chem. 2011, 50, 6856). Here we report trinuclear complexes with a triphenylene backbone. A reaction with triphenylenehexathiol and group 9 metal precursors in the presence of triethylamine gives rise to trinuclear complexes 9-11. The planar structure of 11 is determined using single crystal X-ray diffraction analysis. The ligand-to-metal charge transfer bands of 9-11 move to longer wavelengths compared with those of mononuclear 12-14. Electrochemical measurements disclose that the one-electron and two-electron reduced mixed-valent states are stabilized thermodynamically. Uv-vis-NIR spectroscopy for the reduced species of 9 identifies intervalence charge transfer bands for 9(-) and 9(2-), substantiating the existence of electronic communication among the three metal nuclei. These observations prove that the triphenylene backbone transmits pi-conjugation among the three metalladithiolene units.

  DOI：

  10.1021/ic400110z
• 作为产物：
  描述：

  1,2-苯二甲硫醇 在 iron(III) chloride 、 硼酸三钠 作用下， 反应 6.0h， 以38%的产率得到2,3,6,7,10,11-hexa(methylthio)triphenylene
  参考文献：
  名称：

  JP5731346

  摘要：

  公开号：

文献信息

• An electroactive porous network from covalent metal–dithiolene links
  作者：Jieshun Cui、Zhengtao Xu

  DOI：10.1039/c4cc00408f

  日期：——

  Direct reaction between a hexathiol and PtCl₂ leads to the formation of a covalent metal–organic framework (CMOF) featuring substantial porosity, redox activity and ion exchange capability.

  六硫醇和PtCl2之间的直接反应导致了共价金属-有机框架（CMOF）的形成，具有相当的孔隙度、氧化还原活性和离子交换能力。
• US4631143A
  申请人：——

  公开号：US4631143A

  公开（公告）日：1986-12-23
• JP5731346
  申请人：——

  公开号：——

  公开（公告）日：——
• π-Conjugated Trinuclear Group-9 Metalladithiolenes with a Triphenylene Backbone
  作者：Ryota Sakamoto、Tetsuya Kambe、Satoru Tsukada、Kenji Takada、Ken Hoshiko、Yasutaka Kitagawa、Mitsutaka Okumura、Hiroshi Nishihara

  DOI：10.1021/ic400110z

  日期：2013.7.1

  Previously, we synthesized pi-conjugated trinuclear metalladithiolene complexes based on benzenehexathiol (j. Chem. Soc., Dalton Trans. 1998, 2641; Dalton Trans. 2009, 1939; Inorg. Chem. 2011, 50, 6856). Here we report trinuclear complexes with a triphenylene backbone. A reaction with triphenylenehexathiol and group 9 metal precursors in the presence of triethylamine gives rise to trinuclear complexes 9-11. The planar structure of 11 is determined using single crystal X-ray diffraction analysis. The ligand-to-metal charge transfer bands of 9-11 move to longer wavelengths compared with those of mononuclear 12-14. Electrochemical measurements disclose that the one-electron and two-electron reduced mixed-valent states are stabilized thermodynamically. Uv-vis-NIR spectroscopy for the reduced species of 9 identifies intervalence charge transfer bands for 9(-) and 9(2-), substantiating the existence of electronic communication among the three metal nuclei. These observations prove that the triphenylene backbone transmits pi-conjugation among the three metalladithiolene units.