5,6-diamino-2-(4,5-bis(hexylthio)-1,3-dithio-2-ylidene)benzo[d]-1,3-dithiole | 1169775-83-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,6-diamino-2-(4,5-bis(hexylthio)-1,3-dithio-2-ylidene)benzo[d]-1,3-dithiole
• 英文别名: 5,6-diamino-2-(4,5-bis(hexylthio)-1,3-dithiol-2-ylidene)benzo[d]-1,3-dithiole；2-[4,5-Bis(hexylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-benzodithiole-5,6-diamine
• CAS: 1169775-83-0
• 化学式: C₂₂H₃₂N₂S₆
• 分子量: 516.905
• InChiKey: LUVOASYWVYLEFP-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C(Solvent: Dichloromethane; Hexane)
• 沸点：
  586.4±50.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  204
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2,5,6,9,10-coronene-hexaone 、 5,6-diamino-2-(4,5-bis(hexylthio)-1,3-dithio-2-ylidene)benzo[d]-1,3-dithiole 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以25%的产率得到8,25,42-Tris[4,5-bis(hexylsulfanyl)-1,3-dithiol-2-ylidene]-7,9,24,26,41,43-hexathia-3,13,20,30,37,47-hexazahexadecacyclo[47.6.2.02,14.04,12.06,10.015,54.018,53.019,31.021,29.023,27.032,52.035,51.036,48.038,46.040,44.050,55]heptapentaconta-1(55),2,4,6(10),11,13,15(54),16,18(53),19,21,23(27),28,30,32(52),33,35(51),36,38,40(44),45,47,49,56-tetracosaene
  参考文献：
  名称：

  Star-Shaped Tetrathiafulvalene-Fused Coronene with Large π-Extended Conjugation

  摘要：

  A tristar shaped, planar TTF-fused coronene I was synthesized, its electronic properties have been studied experimentally by the combination of electrochemistry and UV-vis-NIR spectroscopy. Thereby, a nanosized graphite fragment is largely extended in its size, supplemented with a multielectron donor functionality, and shaped to a strongly chromophoric species absorbing intensely in the visible part of the optical spectrum.

  DOI：

  10.1021/jo901054b
• 作为产物：
  描述：

  5,6-diaminobenzene-1,3-dithiole-2-thione 、 4,5-bis(hexylthio)-1,3-dithiol-2-one 在 亚磷酸三乙酯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 5,6-diamino-2-(4,5-bis(hexylthio)-1,3-dithio-2-ylidene)benzo[d]-1,3-dithiole
  参考文献：
  名称：

  液体/固体界面上的环状氧化还原活性分子的扫描探针显微镜研究：烷基链范式的推论

  摘要：

  否决了！自组装的新型基稠合的供体-受体分子（的1包括六氮杂苯并菲和四硫富瓦分支机构）在液/固体界面，研究了STM。发现了具有C 3对称性的二维组装手性多孔网络，这是由熔融单元的扩展π共轭核与HOPG底物的强相互作用强于烷基链的定向力所决定的。

  DOI：

  10.1002/chem.201000017

文献信息

• Tetrathiafulvalene‐Fused Heterabuckybowl: Protonation‐Induced Electron Transfer and Self‐Sensitized Photooxidation
  作者：Lei Liu、Chaoxian Yan、Yecheng Li、Zhe Liu、Chengshan Yuan、Hao‐Li Zhang、Xiangfeng Shao

  DOI：10.1002/chem.201905732

  日期：2020.6.2

  The electron donor tetrathiafulvalene (D1) was fused onto the electron‐rich heterabuckybowl trichalcogenasumanene (D2) through an electron‐deficient pyrazine unit (A) to give 1 c , 1 d , 2 c , and 2 d , featuring the D1–A–D2 structure. Both D1 and D2 play a pivotal role in intramolecular charge‐transfer (ICT) transitions, consequently 1 c , 2 d , 2 c , and 2 d show a broad ICT band at 450–720 nm in

  将电子给体四硫富瓦烯（D 1）通过缺电子的吡嗪单元（A）融合到富电子的杂巴三氯三亚苏曼烯（D 2）上，得到1 c，1 d，2 c和2 d，其特征为D 1 –A–D 2结构。D 1和D 2都在分子内电荷转移（ICT）跃迁中起关键作用，因此1 c，2 d，2 c和2 d在稳定状态下在450-720 nm处显示宽的ICT带。它们表现出两个电荷分离的瞬态CS1和CS 2依次出现。CS 1具有短的寿命（542个FS），以及d 1上CS部分1是在其最大吸收（自由基阳离子状态λ最大）在889纳米。CS 1然后转换成CS 2（λ最大，1105纳米）通过d之间的ICT 1 。+和d 2，得到d 1 （1- δ）。+和d 2 δ。+。化合物1 c，1 d，2 c和2 d显示质子化诱导的分子内电子转移，导致在λ = 700–1300 nm处吸收。由于D 1部分上存在富电子的C = C键，并且吡嗪融合的D 2部分原位生成1
• Near-Infrared Absorbing Compounds Based on π-Extended Tetrathiafulvalene Open-Cage Fullerenes
  作者：Yuming Yu、Liang Xu、Xincheng Huang、Liangbing Gan

  DOI：10.1021/jo5000048

  日期：2014.3.7

  Tetrathiafulvalene (TTF) is attached to open-cage fullerenes through a quinoxaline junction. The resulting linear pi-conjugation system shows intense absorption in the near-infrared region. A unique o-diaminobenzene-induced furan ring formation process from a conjugated 1,4-dione moiety was observed on the rim of a 18-membered orifice.
• Star-Shaped Tetrathiafulvalene-Fused Coronene with Large π-Extended Conjugation
  作者：Hong-Peng Jia、Shi-Xia Liu、Lionel Sanguinet、Eric Levillain、Silvio Decurtins

  DOI：10.1021/jo901054b

  日期：2009.8.7

  A tristar shaped, planar TTF-fused coronene I was synthesized, its electronic properties have been studied experimentally by the combination of electrochemistry and UV-vis-NIR spectroscopy. Thereby, a nanosized graphite fragment is largely extended in its size, supplemented with a multielectron donor functionality, and shaped to a strongly chromophoric species absorbing intensely in the visible part of the optical spectrum.
• A Scanning Probe Microscopy Study of Annulated Redox-Active Molecules at a Liquid/Solid Interface: The Overruling of the Alkyl Chain Paradigm
  作者：Bo Liu、Ying-Fen Ran、Zhihai Li、Shi-Xia Liu、Chunyang Jia、Silvio Decurtins、Thomas Wandlowski

  DOI：10.1002/chem.201000017

  日期：——

  Overruled! The self‐assembly of a novel group of fused donor–acceptor molecules (1) comprising hexaazatriphenylene and tetrathiafulvalene branches was studied by STM at the liquid/solid interface. A 2D assembled chiral porous network with C3 symmetry was found, which is dictated by strong interactions of the extended π‐conjugated cores of the fused units with the HOPG substrate overruling the directional

  否决了！自组装的新型基稠合的供体-受体分子（的1包括六氮杂苯并菲和四硫富瓦分支机构）在液/固体界面，研究了STM。发现了具有C 3对称性的二维组装手性多孔网络，这是由熔融单元的扩展π共轭核与HOPG底物的强相互作用强于烷基链的定向力所决定的。