2-(2-azidoethylthio)-6,7-bis(methylthio)-3-methylthiotetrathiafulvalene | 1190595-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: 2-(2-azidoethylthio)-6,7-bis(methylthio)-3-methylthiotetrathiafulvalene
• 英文别名: 2-(2-azidoethylthio)-3,6,7-tris(methylthio)tetrathiafulvalene；2-[4-(2-Azidoethylsulfanyl)-5-methylsulfanyl-1,3-dithiol-2-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole；2-[4-(2-azidoethylsulfanyl)-5-methylsulfanyl-1,3-dithiol-2-ylidene]-4,5-bis(methylsulfanyl)-1,3-dithiole
• CAS: 1190595-18-6
• 化学式: C₁₁H₁₃N₃S₈
• 分子量: 443.772
• InChiKey: XSXBECOVGLPSIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  217
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2-azidoethylthio)-6,7-bis(methylthio)-3-methylthiotetrathiafulvalene 、 (4-溴苯基乙炔基)三甲基硅烷 在 copper(I) bromide dimethylsulfide complex 、 五甲基二乙烯三胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.0h， 以79%的产率得到1-[2-[[2-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-5-methylsulfanyl-1,3-dithiol-4-yl]sulfanyl]ethyl]-4-(4-bromophenyl)triazole
  参考文献：
  名称：

  用于超分子材料的新型五（四硫富瓦烯基）[60]富勒烯

  摘要：

  合成了带有五个四硫富瓦烯识别单元的新的五（有机）富勒烯供体-受体系统，以促进与嵌套的shuttle相似的自组装，这是由于在富勒烯周围形成了锥形主腔以及π-π和电子互动。

  DOI：

  10.1002/chem.201601038
• 作为产物：
  描述：

  2-(2-hydroxyethylthio)-3,6,7-tris(methylthio)tetrathiafulvalene 在 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到2-(2-azidoethylthio)-6,7-bis(methylthio)-3-methylthiotetrathiafulvalene
  参考文献：
  名称：

  A tetrathiafulvalene–perylene diimide conjugate prepared via click chemistry

  摘要：

  A new tetrathiafulvalene (TTF)-perylene diimide (PDI) conjugate is prepared from an azide-functionalized TTF and an acetylenic PDI employing a Cu(I)-catalyzed Huisgen-Meldal-Sharpless reaction ('click chemistry'). Thus, the TTF donor and PDI acceptor units are linked together by a 1,2,3-triazole unit. The molecules are found to assemble on a mica surface, forming fibrilar structures. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.108

文献信息

• Enhanced Penta(organo)[60]fullerenes by Electroactive Donor Units for Supramolecular Polymers
  作者：Antoine Busseau、Carmen Villegas、Sylvie Dabos-Seignon、Piétrick Hudhomme、Stéphanie Legoupy

  DOI：10.1002/ejoc.201801042

  日期：2018.9.23

  New penta(organo)fullerene donor–acceptor systems bearing five recognition units have been prepared in order to promote their self‐assembly in solution and in the solid state. The host cavity formed due to the perfect organization of electro‐ and/or photoactive substituents around the fullerene, together with π–π and electronic interactions, leads to a supramolecular arrangement similar to shuttlecocks

  已经制备了带有五个识别单元的新型五（有机）富勒烯供体-受体系统，以促进它们在溶液和固态中的自组装。由于富勒烯周围的电和/或光活性取代基的完美组织，加上 π-π 和电子相互作用，形成了类似于相互嵌套的羽毛球的超分子排列。
• Novel clicked tetrathiafulvalene-calix[4]arene assemblies: Synthesis and intermolecular electron transfer toward p-chloranil
  作者：Bang-Tun Zhao、Xiao-Min Zhu、Xiu-Hua Chen、Zhen-Ning Yan、Wei-Min Zhu

  DOI：10.1016/j.cclet.2013.04.026

  日期：2013.7

  Two tetrathiafulvalene-calix[4]arene assemblies (TTF-calix-1 and TTF-calix-2) have been synthesized by the click reaction. Both their cyclic voltammograms show, as expected, two one-electron quasi-reversible redox behavior. The UV-vis absorption spectra studies show that these two assemblies undergo progressive oxidation at the TTF moiety in presence of increasing amounts of Cu2+ or Hg2+. Moreover, the absorption studies show intermolecular electron transfer between compounds TTF-calix-1 or TTF-calix-2 and p-chloranil may be promoted by specific metal ions such as Pb2+, Sc3+ etc. (c) 2013 Bang-Tun Zhao and Wei-Min Zhu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Metal-Promoted Intermolecular Electron Transfer in Tetrathiafulvalene–Thiacalix[4]arene Conjugates and Tetrachlorobenzoquinone
  作者：Bang-Tun Zhao、Qi-Ming Peng、Xiao-Min Zhu、Zhen-Ning Yan、Wei-Min Zhu

  DOI：10.1021/jo502390z

  日期：2015.1.16

  In this work, two series of tetrathiafulvalene (TTF) and thiacalix[4]arene (TCA) conjugates (TTFTCA) were designed by CuAAC click reactions. The results obtained from NMR and H-1 NMR NOE indicated that their conformations of thiacalix[4]arene framework may prefer to 1,3-alternate. The cyclic voltammograms of four TTFTCA compounds containing electroactive TTF units were provided. Meanwhile, their intermolecular electron-transfer (ET) behaviors with tetrachlorobenzoquinone (Q) mediated by different metal ions, Sc3+, Pb2+, Ag+, Cd2+, and Zn2+, in CH3CNCH2Cl2 (V/V = 1:1) solution were studied and analyzed via UVvis spectroscopy. It was determined that intermolecular ET between each TTFTCA and Q ensemble was not observed without introduction of the metal ions mentioned above. The added specified metal ions most likely induced the intermolecular ET between TTFTCA and Q ensemble, and the effects of Sc3+ functions were the most imperative. The intermolecular ET also proved to be reliant on the structure of TTFTCA, where TTFTCA 7a and 7b were more effective than TTFTCA 6a and 6b. The difference may be credited to TTFTCA 7a or 7b possessing two independent TTF pendants and providing a more synergic coordination among the TTF radical cation and Q radical anion with a metal ion.
• New Penta(tetrathiafulvalenyl)[60]fullerenes for Supramolecular Materials
  作者：Antoine Busseau、Carmen Villegas、Sylvie Dabos-Seignon、Clément Cabanetos、Piétrick Hudhomme、Stéphanie Legoupy

  DOI：10.1002/chem.201601038

  日期：2016.6.13

  New penta(organo)fullerenes donor–acceptor systems bearing five tetrathiafulvalene recognition units have been synthesized to promote self‐assemblies similar in appearance to shuttlecocks nested into each other thanks to the conical host cavity created around the fullerene together with the π–π and electronic interactions.

  合成了带有五个四硫富瓦烯识别单元的新的五（有机）富勒烯供体-受体系统，以促进与嵌套的shuttle相似的自组装，这是由于在富勒烯周围形成了锥形主腔以及π-π和电子互动。
• A tetrathiafulvalene–perylene diimide conjugate prepared via click chemistry
  作者：Katrine Qvortrup、Michael Åxman Petersen、Tue Hassenkam、Mogens Brøndsted Nielsen

  DOI：10.1016/j.tetlet.2009.07.108

  日期：2009.10

  A new tetrathiafulvalene (TTF)-perylene diimide (PDI) conjugate is prepared from an azide-functionalized TTF and an acetylenic PDI employing a Cu(I)-catalyzed Huisgen-Meldal-Sharpless reaction ('click chemistry'). Thus, the TTF donor and PDI acceptor units are linked together by a 1,2,3-triazole unit. The molecules are found to assemble on a mica surface, forming fibrilar structures. (C) 2009 Elsevier Ltd. All rights reserved.