| 856898-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• CAS: 856898-81-2
• 化学式: C₇₈H₉₂S₈
• 分子量: 1286.12
• InChiKey: IAHGPGGVTNQOGH-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C(Solvent: Hexane)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  25.93
• 重原子数：
  86.0
• 可旋转键数：
  28.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 sodium sulfide 、 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 22.0h， 以17%的产率得到[3.3]quinquethiophenophane
  参考文献：
  名称：

  Syntheses, Structures, Spectroscopic Properties, and π-Dimeric Interactions of [n.n]Quinquethiophenophanes

  摘要：

  A cyclophane-type of dimeric quinquethiophenes (4a-e) with the bridge chains consecutively varying from two to six methylenes has been synthesized and studied as ideal pi-dimer models. The double-decker structures of these compounds are verified by upfield shifts for the proton NMR signals of the inside thiophenes, as compared to those of monomeric dimethylquinquethiophene (3). The electronic absorption and emission spectra of 4a-e are perturbed by through-space g-electronic interactions involving exciton-exciton coupling between the two overlapped quinquethiophenes, which become marked with shortening of the bridged alkylene chains. One-electron oxidation of 4a-e with FeCl3 in dichloromethane results in the appearance of specific polaronic bands in the near-infrared region of the electronic absorption spectra, due to the generation of a radical cation species (polaron) on one of the quinquethiophenes, which electronically interacts with the remaining neutral species. Two-electron oxidation of 4a-e introduces spectral changes, revealing that the resulting two quinquethiophene radical cations readily form an intramolecular,pi-dimer, thanks to their close stacking, in contrast to the difficult formation of an intermolecular pi-dimer from 3. The pi-dimeric spectra of 4b-e are comprised of two strong absorption bands, similar to that of 3, the low-energy band of which is considerably red-shifted by an effective pi-dimeric interaction depending on the lengths of the bridged alkylene chains. Quite different is the spectrum of 4a with three absorption bands inherent in pi-dimer, presumably because the two short bridging chains of 4a force the pi-dimer to take a constrained, strongly interactive structure.

  DOI：

  10.1021/ja050783u
• 作为产物：
  描述：

  1,2-bis(3'-octyl-2,2'-bithien-5-yl)propane 在 吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 copper diacetate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 51.0h， 生成
  参考文献：
  名称：

  Syntheses, Structures, Spectroscopic Properties, and π-Dimeric Interactions of [n.n]Quinquethiophenophanes

  摘要：

  A cyclophane-type of dimeric quinquethiophenes (4a-e) with the bridge chains consecutively varying from two to six methylenes has been synthesized and studied as ideal pi-dimer models. The double-decker structures of these compounds are verified by upfield shifts for the proton NMR signals of the inside thiophenes, as compared to those of monomeric dimethylquinquethiophene (3). The electronic absorption and emission spectra of 4a-e are perturbed by through-space g-electronic interactions involving exciton-exciton coupling between the two overlapped quinquethiophenes, which become marked with shortening of the bridged alkylene chains. One-electron oxidation of 4a-e with FeCl3 in dichloromethane results in the appearance of specific polaronic bands in the near-infrared region of the electronic absorption spectra, due to the generation of a radical cation species (polaron) on one of the quinquethiophenes, which electronically interacts with the remaining neutral species. Two-electron oxidation of 4a-e introduces spectral changes, revealing that the resulting two quinquethiophene radical cations readily form an intramolecular,pi-dimer, thanks to their close stacking, in contrast to the difficult formation of an intermolecular pi-dimer from 3. The pi-dimeric spectra of 4b-e are comprised of two strong absorption bands, similar to that of 3, the low-energy band of which is considerably red-shifted by an effective pi-dimeric interaction depending on the lengths of the bridged alkylene chains. Quite different is the spectrum of 4a with three absorption bands inherent in pi-dimer, presumably because the two short bridging chains of 4a force the pi-dimer to take a constrained, strongly interactive structure.

  DOI：

  10.1021/ja050783u