Spiro[acenaphthene-1,2'-(1',3'-benzodithiole)]

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Spiro[acenaphthene-1,2'-(1',3'-benzodithiole)]
• 英文别名: spiro[1,3-benzodithiole-2,2'-1H-acenaphthylene]
• 化学式: C₁₈H₁₂S₂
• 分子量: 292.425
• InChiKey: LRQSCCPNIUWSJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Spiro[acenaphthene-1,2'-(1',3'-benzodithiole)] 在 四氯化碲 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Acenaphthyleno[1,2-b][1,4]benzodithiine
  参考文献：
  名称：

  New π-electron donor systems based on acenaphtho[1,2-b][1,4]dithiine

  摘要：

  Syntheses of the acenaphtho[1,2-b] [1,4] dithiine derivatives 12, 25 and 29 are reported. Cyclic voltammetric studies reveal that these compounds undergo reversible single-electron oxidations at < 1.0 V, vs. Ag/AgCl. Lithiation of compound 12 with BuLi (2 equiv.) followed by addition of either methyl iodide or ethyl chloroformate yielded the unstable ring-opened acetylene derivatives 22a and 22b, respectively. A new synthesis of 1,2-diselenine derivative 33 is reported. Compound 25 formed 1:1 charge-transfer complexes with 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) and with 2,5-dibromo-TCNQ, both of which were electrical insulators. The X-ray crystal structures of compound 25, a charge-transfer complex 25:Br,TCNQ (1:1 stoichiometry) and compound 33 are reported. In the structure of 25:Br,TCNQ, molecules of 25 and Br,TCNQ form mixed stacks. The folding of the donor along the S ... S vector in the complex is 17 degrees (ef. 48 degrees in pure 25) and the conformation of 25 is discussed in the light of previous studies on 1,4-dithiine derivatives. An interesting feature of the crystal structure of 33 is the formation of pseudo-dimers with two short intermolecular Se Se contacts.

  DOI：

  10.1039/p19960002451
• 作为产物：
  描述：

  1-羟基二氢苊 在 铬酸 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 48.08h， 生成 Spiro[acenaphthene-1,2'-(1',3'-benzodithiole)]
  参考文献：
  名称：

  New π-electron donor systems based on acenaphtho[1,2-b][1,4]dithiine

  摘要：

  Syntheses of the acenaphtho[1,2-b] [1,4] dithiine derivatives 12, 25 and 29 are reported. Cyclic voltammetric studies reveal that these compounds undergo reversible single-electron oxidations at < 1.0 V, vs. Ag/AgCl. Lithiation of compound 12 with BuLi (2 equiv.) followed by addition of either methyl iodide or ethyl chloroformate yielded the unstable ring-opened acetylene derivatives 22a and 22b, respectively. A new synthesis of 1,2-diselenine derivative 33 is reported. Compound 25 formed 1:1 charge-transfer complexes with 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) and with 2,5-dibromo-TCNQ, both of which were electrical insulators. The X-ray crystal structures of compound 25, a charge-transfer complex 25:Br,TCNQ (1:1 stoichiometry) and compound 33 are reported. In the structure of 25:Br,TCNQ, molecules of 25 and Br,TCNQ form mixed stacks. The folding of the donor along the S ... S vector in the complex is 17 degrees (ef. 48 degrees in pure 25) and the conformation of 25 is discussed in the light of previous studies on 1,4-dithiine derivatives. An interesting feature of the crystal structure of 33 is the formation of pseudo-dimers with two short intermolecular Se Se contacts.

  DOI：

  10.1039/p19960002451