2,3-bis(2-cyanoethylthio)-6,7-bis(3,5-di-tert-butylbenzylthio)-1,4,5,8-tetrathiafulvalene | 1204138-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-bis(2-cyanoethylthio)-6,7-bis(3,5-di-tert-butylbenzylthio)-1,4,5,8-tetrathiafulvalene
• 英文别名: 3-[[2-[4,5-Bis[(3,5-ditert-butylphenyl)methylsulfanyl]-1,3-dithiol-2-ylidene]-5-(2-cyanoethylsulfanyl)-1,3-dithiol-4-yl]sulfanyl]propanenitrile；3-[[2-[4,5-bis[(3,5-ditert-butylphenyl)methylsulfanyl]-1,3-dithiol-2-ylidene]-5-(2-cyanoethylsulfanyl)-1,3-dithiol-4-yl]sulfanyl]propanenitrile
• CAS: 1204138-61-3
• 化学式: C₄₂H₅₄N₂S₈
• 分子量: 843.432
• InChiKey: GLACMXUEXGHPKL-UHFFFAOYSA-N

物化性质

• 沸点：
  764.3±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  250
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3-bis(2-cyanoethylthio)-6,7-bis(3,5-di-tert-butylbenzylthio)-1,4,5,8-tetrathiafulvalene 、 四溴甲苯 在 cesium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 以67%的产率得到2,10-bis[4,5-bis(3,5-di-tert-butylbenzylthio)-1,3-dithiol-2-ylidene]-5H,7H,13H,15H-bis[1,3]dithiolo[4,5-b:4',5'-b']benzo[1,2-f:4,5-f']bis[1,4]dithiocine
  参考文献：
  名称：

  Redox responsive molecular tweezers with tetrathiafulvalene units: synthesis, electrochemistry, and binding properties

  摘要：

  Several new molecular tweezers with tetrathiafulvalene (TTF) arms as well as mono-TTF derivatives bearing 3,5-di-tert-butylbenzylthio groups to provide enhanced solubility were prepared starting from a bis-cyanoethyl-protected tetrathiafulvalene derivative. The X-ray crystallographic analysis of 3 and 7a showed highly distorted TTF groups and absence of close TTF-TTF contacts in the crystalline state. Comparative cyclic voltammetry (CV) measurements demonstrated that through space distance-dependent TTF-TTF interactions take place in the TTF-containing molecular tweezers, leading to electronic pairing with formation of mixed valence [TTF](2)(+center dot) species and splitting of the first oxidation wave. TTF-containing molecular tweezers were successfully tested as receptors for several electron-deficient substances. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.052
• 作为产物：
  描述：

  4,5-bis(3,5-di-tert-butylbenzylthio)-1,3-dithiole-2-thione 、 4,5-双(2-氰乙基硫代)-1,2-二硫醇-2-酮 在 亚磷酸三乙酯 作用下， 反应 2.0h， 以46%的产率得到2,3-bis(2-cyanoethylthio)-6,7-bis(3,5-di-tert-butylbenzylthio)-1,4,5,8-tetrathiafulvalene
  参考文献：
  名称：

  Redox responsive molecular tweezers with tetrathiafulvalene units: synthesis, electrochemistry, and binding properties

  摘要：

  Several new molecular tweezers with tetrathiafulvalene (TTF) arms as well as mono-TTF derivatives bearing 3,5-di-tert-butylbenzylthio groups to provide enhanced solubility were prepared starting from a bis-cyanoethyl-protected tetrathiafulvalene derivative. The X-ray crystallographic analysis of 3 and 7a showed highly distorted TTF groups and absence of close TTF-TTF contacts in the crystalline state. Comparative cyclic voltammetry (CV) measurements demonstrated that through space distance-dependent TTF-TTF interactions take place in the TTF-containing molecular tweezers, leading to electronic pairing with formation of mixed valence [TTF](2)(+center dot) species and splitting of the first oxidation wave. TTF-containing molecular tweezers were successfully tested as receptors for several electron-deficient substances. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.052

文献信息

• Calix[4]arenes with 1,2- and 1,3-upper rim tetrathiafulvalene bridges
  作者：Matthias H. Düker、Felix Kutter、Thomas Dülcks、Vladimir A. Azov

  DOI：10.1080/10610278.2013.872245

  日期：2014.8.3

  Herein we report the synthesis of several calix[4]arene derivatives with tetrathiafulvalene bridges at the upper rim. Calix[4]arene-tetrathiafulvalene (TTF) conjugates 4a–d, fixed in cone conformation and comprising two smaller 1,2-bridges, were prepared by cyclisation of tetrakis-chloromethylated calix[4]arene 1 with 2,3-dithiolates of TTFs. Larger calix[4]arene-TTF macrocycles 14 and 15, also in

  在这里，我们报告了几种杯[4]芳烃衍生物的合成，在上缘具有四硫富瓦烯桥。杯[4] 芳烃-四硫富瓦烯 (TTF) 共轭物 4a-d，固定为锥形构象并包含两个较小的 1,2-桥，通过四氯甲基化杯 [4] 芳烃 1 与 2,3-二硫醇盐的环化制备TTF。较大的杯 [4] 芳烃-TTF 大环 14 和 15，同样为锥形构象，包含 1,3-桥，通过用双溴甲基化杯 [4] 环化 TTF 的 2,6- 和 2,7-二硫醇盐合成芳烃 7. 使用循环伏安法表征新杯[4]芳烃-TTF缀合物的氧化还原特性。
• Upper rim tetrathiafulvalene-bridged calix[4]arenes
  作者：Matthias H. Düker、Rafael Gómez、Christophe M.L. Vande Velde、Vladimir A. Azov

  DOI：10.1016/j.tetlet.2011.03.140

  日期：2011.6

  The synthesis of novel upper rim calix[4]arene-tetrathiafulvalene conjugates 1a-d has been performed by bridging the tetrachloromethylated calix[4]arene derivative 4 with the corresponding tetrathiafulvalene-dithiolates. The cyclic voltammetry of 1a-d shows a two-step oxidation behavior, whereas NMR binding titrations showed their binding affinity to pyridinium salts. X-ray structure of 4 features calixarene fixed in the pinched cone conformation; its crystal packing is defined by the network of C-H center dot center dot center dot Cl weak hydrogen bonds. (C) 2011 Elsevier Ltd. All rights reserved.
• Redox responsive molecular tweezers with tetrathiafulvalene units: synthesis, electrochemistry, and binding properties
  作者：Maciej Skibiński、Rafael Gómez、Enno Lork、Vladimir A. Azov

  DOI：10.1016/j.tet.2009.10.052

  日期：2009.12

  Several new molecular tweezers with tetrathiafulvalene (TTF) arms as well as mono-TTF derivatives bearing 3,5-di-tert-butylbenzylthio groups to provide enhanced solubility were prepared starting from a bis-cyanoethyl-protected tetrathiafulvalene derivative. The X-ray crystallographic analysis of 3 and 7a showed highly distorted TTF groups and absence of close TTF-TTF contacts in the crystalline state. Comparative cyclic voltammetry (CV) measurements demonstrated that through space distance-dependent TTF-TTF interactions take place in the TTF-containing molecular tweezers, leading to electronic pairing with formation of mixed valence [TTF](2)(+center dot) species and splitting of the first oxidation wave. TTF-containing molecular tweezers were successfully tested as receptors for several electron-deficient substances. (C) 2009 Elsevier Ltd. All rights reserved.