5,6-diamino-2-[4,5-bis(decylthio)-1,3-dithio-2-ylidene]-benzo[d]-1,3-dithiole | 1233730-95-4

• 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(decylthio)-1,3-dithio-2-ylidene]-benzo[d]-1,3-dithiole
• 英文别名: 5,6-diamino-2-(4,5-bis(decylthio)-1,3-dithio-2-ylidene)benzo[d]-1,3-dithiole；2-[4,5-Bis(decylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-benzodithiole-5,6-diamine；2-[4,5-bis(decylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-benzodithiole-5,6-diamine
• CAS: 1233730-95-4
• 化学式: C₃₀H₄₈N₂S₆
• 分子量: 629.121
• InChiKey: JPOKGEIIHUKCHB-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C
• 沸点：
  667.0±55.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  38
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  5-nitro-acenaphthylene-1,2-dione 、 5,6-diamino-2-[4,5-bis(decylthio)-1,3-dithio-2-ylidene]-benzo[d]-1,3-dithiole 在 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.0h， 以87%的产率得到8-[4,5-Bis(decylsulfanyl)-1,3-dithiol-2-ylidene]-18-nitro-7,9-dithia-3,13-diazahexacyclo[13.7.1.02,14.04,12.06,10.019,23]tricosa-1(22),2,4,6(10),11,13,15(23),16,18,20-decaene
  参考文献：
  名称：

  Structure-property relationships in conjugated donor–acceptor systems functionalized with tetrathiafulvalene

  摘要：

  通过溶液状态研究（电化学、吸收、自组装）和理论计算（DFT、TD-DFT），研究了四硫富戊烯-苊并[1,2-b]喹喔啉（1）和四硫富戊烯-3-硝基-苊并[1,2-b]喹喔啉（2）这两种供体-受体化合物的性质。电化学研究表明，硝基取代对其氧化还原特性的影响可以忽略不计。这两种化合物在溶液的紫外-可见光范围内都显示出有效的分子内电荷转移（ICT）转变。与化合物 1 相比，化合物 2 的吸收光谱发生了浴色偏移，δ "maxâICT 从 20â800 cmâ1 扩展到 19â700 cmâ1 （480 纳米到 507 纳米）。此外，当使用硝基时，这两种化合物的自组装特性发生了很大变化，从带状纳米结构变成了根状纳米结构。密度泛函理论（DFT）计算深入揭示了这两种化合物的分子几何结构、电子结构和物理化学性质。

  DOI：

  10.1039/c1nj20384c
• 作为产物：
  描述：

  5,6-diaminobenzene-1,3-dithiole-2-thione 、 4,5-bis(decylthio)-1,3-dithiole-2-oxone 在 亚磷酸三乙酯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以45%的产率得到5,6-diamino-2-[4,5-bis(decylthio)-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

• 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。
• Synthesis, physical properties and self-assembly of conjugated donor–acceptor system based on tetrathiafulvalene and functionalized with binding sites
  作者：Chunyang Jia、Jiaqiang Zhang、Jingying Bai、Ligong Zhang、Zhongquan Wan、Xiaojun Yao

  DOI：10.1016/j.dyepig.2012.02.008

  日期：2012.9

  A novel π-conjugated donor–acceptor compound (1) based on tetrathiafulvalene (TTF), which is functionalized with dipyridine, has been designed and synthesized. Spectroscopic and electrochemical behaviors of compound 1 demonstrate that the donor (TTF) unit strongly interacts with the electron-accepting group through the heteroaromatic bridge. The interaction of compound 1 with metallic ions can cause

  设计并合成了一种基于四硫富瓦烯（TTF）的新型π共轭供体-受体化合物（1），该化合物已被二吡啶官能化。化合物1的光谱和电化学行为表明，供体（TTF）单元通过杂芳族桥与电子接受基团发生强烈相互作用。化合物1与金属离子的相互作用会导致吸收光谱和荧光光谱发生显着变化。DFT计算表明，吡嗪环与TTF平面几乎共面，这有利于供体和受体的电子通讯。此外，化合物1 可以自组装成具有光滑表面，宽度为百纳米，长度为十微米的纳米结构。
• Highly conjugated donor–acceptor dyad based on tetrathiafulvalene covalently attached to porphyrin unit
  作者：Zhongquan Wan、Chunyang Jia、Jiaqiang Zhang、Xiaojun Yao、Yu Shi

  DOI：10.1016/j.dyepig.2011.10.011

  日期：2012.4

  A novel and highly conjugated donor-acceptor dyad consisting of tetrathiafulvalene unit covalently attached to a porphyrin unit has been synthesized and characterized. As compared to tetraphenylporphyrin, the fluorescence intensity and lifetime of the dyad was decreased owing to photoinduced electron transfer between the tetrathiafulvalene and porphyrin units in the excited state. The fluorescence intensity of the dyad was recovered dramatically upon the addition of Fe(ClO4)(3)center dot 6H(2)O to a solution of the dyad, and the fluorescence intensity grows with an increasing amount of Fe(ClO4)(3)center dot 6H(2)O. More importantly, the fluorescence intensity of the dyad can be reversibly modulated by the sequential electrochemical oxidation and reduction of the tetrathiafulvalene unit, thus a new redox fluorescence switch based on this dyad has been constructed. (C) 2011 Elsevier Ltd. All rights reserved.
• Structure-property relationships in conjugated donor–acceptor systems functionalized with tetrathiafulvalene
  作者：Chunyang Jia、Jiaqiang Zhang、Ligong Zhang、Xiaojun Yao

  DOI：10.1039/c1nj20384c

  日期：——

  The properties of two donor–acceptor compounds tetrathiafulvalene-acenaphtho[1,2-b] quinoxaline (1) and tetrathiafulvalene-3-nitro-acenaphtho[1,2-b]quinoxaline (2) have been investigated by solution-state studies (electrochemistry, absorption, self-assembly) and theoretical calculations (DFT, TD-DFT). The electrochemical studies indicate the nitro-substituted effect on their redox properties is negligible. Both compounds show effective intramolecular charge transfer (ICT) transitions in the UV-Visible range in solution. Compared with compound 1, compound 2 has a bathochromic shift in the absorption spectra, the λmax−ICT has been extended from 20 800 cm−1 to 19 700 cm−1 (480 nm to 507 nm). In addition, when the nitro group is employed, the self-assembly characteristics of the two compounds are substantially changed from ribbon-like nanostructures to root-like nanostructures. Density functional theory (DFT) calculations provide insights into their molecular geometries, electronic structures, and physico-chemical properties.

  通过溶液状态研究（电化学、吸收、自组装）和理论计算（DFT、TD-DFT），研究了四硫富戊烯-苊并[1,2-b]喹喔啉（1）和四硫富戊烯-3-硝基-苊并[1,2-b]喹喔啉（2）这两种供体-受体化合物的性质。电化学研究表明，硝基取代对其氧化还原特性的影响可以忽略不计。这两种化合物在溶液的紫外-可见光范围内都显示出有效的分子内电荷转移（ICT）转变。与化合物 1 相比，化合物 2 的吸收光谱发生了浴色偏移，δ "maxâICT 从 20â800 cmâ1 扩展到 19â700 cmâ1 （480 纳米到 507 纳米）。此外，当使用硝基时，这两种化合物的自组装特性发生了很大变化，从带状纳米结构变成了根状纳米结构。密度泛函理论（DFT）计算深入揭示了这两种化合物的分子几何结构、电子结构和物理化学性质。
• A Novel Conjugated Donor-Acceptor System Based on Tetrathiafulvalene Merging Pyrene Unit: Synthesis, Physical Properties and Theoretical Calculations
  作者：Chunyang Jia、Jiaqiang Zhang、Ligong Zhang、Xiaojun Yao

  DOI：10.3987/com-11-12177

  日期：——

  A novel conjugated donor-acceptor compound (1) based on tetrathiafulvalene has been synthesized and fully characterized. Intramolecular charge transfer (ICT) in compound 1, arising from HOMO-LUMO singlet transitions, has been experimentally evidenced through absorption/fluorescence spectra and theoretical calculations.