2-[4-[3-[2-[2-(4,5-Dihexyl-1,3-dithiol-2-ylidene)-1,3-dithiol-4-yl]ethynyl]-6-(4-nitrophenyl)-4-[2-(4-nitrophenyl)ethynyl]hex-3-en-1,5-diynyl]-1,3-dithiol-2-ylidene]-4,5-dihexyl-1,3-dithiole | 1092717-94-6

• 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-[3-[2-[2-(4,5-Dihexyl-1,3-dithiol-2-ylidene)-1,3-dithiol-4-yl]ethynyl]-6-(4-nitrophenyl)-4-[2-(4-nitrophenyl)ethynyl]hex-3-en-1,5-diynyl]-1,3-dithiol-2-ylidene]-4,5-dihexyl-1,3-dithiole
• CAS: 1092717-94-6
• 化学式: C₅₈H₆₂N₂O₄S₈
• 分子量: 1107.67
• InChiKey: VHRNSVYSPVHKOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.6
• 重原子数：
  72
• 可旋转键数：
  28
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  294
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-[dibromomethylidene]-1,5-bis[4-nitrophenyl]penta-1,4-diyne 、 4-ethynyl-4',5'-dihexyltetrathiafulvalene 在 copper(l) iodide 、 二(三叔丁基膦)钯 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 以40%的产率得到2-[4-[3-[2-[2-(4,5-Dihexyl-1,3-dithiol-2-ylidene)-1,3-dithiol-4-yl]ethynyl]-6-(4-nitrophenyl)-4-[2-(4-nitrophenyl)ethynyl]hex-3-en-1,5-diynyl]-1,3-dithiol-2-ylidene]-4,5-dihexyl-1,3-dithiole
  参考文献：
  名称：

  Synthesis and Characterization of Tetrathiafulvalene-Substituted Di- and Tetraethynylethenes with p-Nitrophenyl Acceptors

  摘要：

  Novel di- and tetraethynylethene (DEE and TEE) compounds functionalized with tetrathiafulvalene (TTF) donor groups and p-nitrophenyl acceptor groups were synthesized by palladium-catalyzed cross-coupling reactions under various conditions. The molecules are strong chromophores and were investigated for their optical properties. Placement of two TTFs and two p-nitrophenyls about a central TEE core provides a molecule with a high third-order optical nonlinearity. The molecules experience reversible oxidations of the TTF units, and the optical properties of the oxidized species were elucidated by spectroelectrochemistry. The degree of quinoid character of the p-nitrophenyl in the molecules was determined by X-ray crystallography.

  DOI：

  10.1021/jo802190q

文献信息

• Synthesis and Characterization of Tetrathiafulvalene-Substituted Di- and Tetraethynylethenes with <i>p</i>-Nitrophenyl Acceptors
  作者：Asbjørn S. Andersson、Lasse Kerndrup、Anders Ø. Madsen、Kristine Kilså、Mogens Brøndsted Nielsen、Philip R. La Porta、Ivan Biaggio

  DOI：10.1021/jo802190q

  日期：2009.1.2

  Novel di- and tetraethynylethene (DEE and TEE) compounds functionalized with tetrathiafulvalene (TTF) donor groups and p-nitrophenyl acceptor groups were synthesized by palladium-catalyzed cross-coupling reactions under various conditions. The molecules are strong chromophores and were investigated for their optical properties. Placement of two TTFs and two p-nitrophenyls about a central TEE core provides a molecule with a high third-order optical nonlinearity. The molecules experience reversible oxidations of the TTF units, and the optical properties of the oxidized species were elucidated by spectroelectrochemistry. The degree of quinoid character of the p-nitrophenyl in the molecules was determined by X-ray crystallography.