2-[9,10-Bis(1,3-dithiol-2-ylidene)anthracen-2-yl]-1,3-dioxane | 194299-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-[9,10-Bis(1,3-dithiol-2-ylidene)anthracen-2-yl]-1,3-dioxane
• CAS: 194299-35-9
• 化学式: C₂₄H₁₈O₂S₄
• 分子量: 466.67
• InChiKey: FQMMKZPCGKZHDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[9,10-Bis(1,3-dithiol-2-ylidene)anthracen-2-yl]-1,3-dioxane 在 盐酸 作用下， 以 丙酮 为溶剂， 以98%的产率得到2-formyl-9,10-bis(1,3-dithiol-2-ylidene)dihydroanthracene
  参考文献：
  名称：

  Synthesis and Properties of the First Highly Conjugated Tetrathiafulvalene Analogues Covalently Attached to [60]Fullerene

  摘要：

  The synthesis of the first C-60-based donor-acceptor (D-A) systems (12a-c) in which the C-60 core is covalently linked to strong, highly conjugated pi-electron donors derived of tetrathiafulvalene (TTF) with p-quinodimethane structure has been carried out by cyclization with azomethine ylides following Prate's procedure. The synthetic strategy requires the preparation of the novel formyl-substituted pi-extended donors which, in turn, are prepared in a multistep synthetic procedure by reaction of 2-formyl-9,10-anthraquinone (6) with the appropriately substituted phosphonate esters (8). Semiempirical PM3 calculations predict a geometry highly distorted from planarity for the donor fragment and a most stable conformation in which both 1,3-dithiole rings are far away from the [60]fullerene surface. The redox properties were determined by cyclic voltammetry in solution and reveal the presence of four cathodically shifted reduction waves, relative to C-60 and corresponding to the C-60 core, and a two-electron single oxidation wave to form stable dication species of the pi-extended donor units. Magnetic susceptibility measurements clearly indicate a paramagnetic behavior in the solid state, and a remarkable conductivity is observed for these single component organic compounds.

  DOI：

  10.1021/jo970320+
• 作为产物：
  描述：

  2-羟甲基蒽醌 在 正丁基锂 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 61.0h， 生成 2-[9,10-Bis(1,3-dithiol-2-ylidene)anthracen-2-yl]-1,3-dioxane
  参考文献：
  名称：

  Synthesis and Properties of the First Highly Conjugated Tetrathiafulvalene Analogues Covalently Attached to [60]Fullerene

  摘要：

  The synthesis of the first C-60-based donor-acceptor (D-A) systems (12a-c) in which the C-60 core is covalently linked to strong, highly conjugated pi-electron donors derived of tetrathiafulvalene (TTF) with p-quinodimethane structure has been carried out by cyclization with azomethine ylides following Prate's procedure. The synthetic strategy requires the preparation of the novel formyl-substituted pi-extended donors which, in turn, are prepared in a multistep synthetic procedure by reaction of 2-formyl-9,10-anthraquinone (6) with the appropriately substituted phosphonate esters (8). Semiempirical PM3 calculations predict a geometry highly distorted from planarity for the donor fragment and a most stable conformation in which both 1,3-dithiole rings are far away from the [60]fullerene surface. The redox properties were determined by cyclic voltammetry in solution and reveal the presence of four cathodically shifted reduction waves, relative to C-60 and corresponding to the C-60 core, and a two-electron single oxidation wave to form stable dication species of the pi-extended donor units. Magnetic susceptibility measurements clearly indicate a paramagnetic behavior in the solid state, and a remarkable conductivity is observed for these single component organic compounds.

  DOI：

  10.1021/jo970320+

文献信息

• Synthesis and Properties of the First Highly Conjugated Tetrathiafulvalene Analogues Covalently Attached to [60]Fullerene
  作者：Nazario Martín、Ignacio Pérez、Luis Sánchez、Carlos Seoane

  DOI：10.1021/jo970320+

  日期：1997.8.1

  The synthesis of the first C-60-based donor-acceptor (D-A) systems (12a-c) in which the C-60 core is covalently linked to strong, highly conjugated pi-electron donors derived of tetrathiafulvalene (TTF) with p-quinodimethane structure has been carried out by cyclization with azomethine ylides following Prate's procedure. The synthetic strategy requires the preparation of the novel formyl-substituted pi-extended donors which, in turn, are prepared in a multistep synthetic procedure by reaction of 2-formyl-9,10-anthraquinone (6) with the appropriately substituted phosphonate esters (8). Semiempirical PM3 calculations predict a geometry highly distorted from planarity for the donor fragment and a most stable conformation in which both 1,3-dithiole rings are far away from the [60]fullerene surface. The redox properties were determined by cyclic voltammetry in solution and reveal the presence of four cathodically shifted reduction waves, relative to C-60 and corresponding to the C-60 core, and a two-electron single oxidation wave to form stable dication species of the pi-extended donor units. Magnetic susceptibility measurements clearly indicate a paramagnetic behavior in the solid state, and a remarkable conductivity is observed for these single component organic compounds.