2-[4,5-bis(3,5-di-tert-butylbenzylthio)-1,3-dithiol-2-ylidene]-5H,10H-1,3-dithiolo[4,5-c][2,5]benzodithiocine | 1204138-64-6

• 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-[4,5-bis(3,5-di-tert-butylbenzylthio)-1,3-dithiol-2-ylidene]-5H,10H-1,3-dithiolo[4,5-c][2,5]benzodithiocine
• 英文别名: 2-[4,5-Bis[(3,5-ditert-butylphenyl)methylsulfanyl]-1,3-dithiol-2-ylidene]-5,10-dihydro-[1,3]dithiolo[4,5-c][2,5]benzodithiocine；2-[4,5-bis[(3,5-ditert-butylphenyl)methylsulfanyl]-1,3-dithiol-2-ylidene]-5,10-dihydro-[1,3]dithiolo[4,5-c][2,5]benzodithiocine
• CAS: 1204138-64-6
• 化学式: C₄₄H₅₄S₈
• 分子量: 839.441
• InChiKey: PUJCPXONWYXOEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  52
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  202
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3-bis(2-cyanoethylthio)-6,7-bis(3,5-di-tert-butylbenzylthio)-1,4,5,8-tetrathiafulvalene 、 1,2-二(溴甲基)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76%的产率得到2-[4,5-bis(3,5-di-tert-butylbenzylthio)-1,3-dithiol-2-ylidene]-5H,10H-1,3-dithiolo[4,5-c][2,5]benzodithiocine
  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

• 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.