3,3'''''-(1,19-dithia-4,7,10,13,15-pentaoxa-1,19-nonadecanediyl)-2,2':5',2'':5'':2''':5''',2'''':5'''',2'''''-sexithiophene | 499793-42-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,3'''''-(1,19-dithia-4,7,10,13,15-pentaoxa-1,19-nonadecanediyl)-2,2':5',2'':5'':2''':5''',2'''':5'''',2'''''-sexithiophene
• 英文别名: 22,25,28,31,34-Pentaoxa-15,19,37,41,46,47,48,49-octathiaheptacyclo[41.2.1.12,5.16,9.110,13.014,18.038,42]nonatetraconta-1(45),2,4,6,8,10,12,14(18),16,38(42),39,43-dodecaene；22,25,28,31,34-pentaoxa-15,19,37,41,46,47,48,49-octathiaheptacyclo[41.2.1.12,5.16,9.110,13.014,18.038,42]nonatetraconta-1(45),2,4,6,8,10,12,14(18),16,38(42),39,43-dodecaene
• CAS: 499793-42-9
• 化学式: C₃₆H₃₆O₅S₈
• 分子量: 805.207
• InChiKey: BCMGQMRTQWURGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  49
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  266
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  lead(II) perchlorate 、 3,3'''''-(1,19-dithia-4,7,10,13,15-pentaoxa-1,19-nonadecanediyl)-2,2':5',2'':5'':2''':5''',2'''':5'''',2'''''-sexithiophene 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Crown-Annelated Oligothiophenes as Model Compounds for Molecular Actuation

  摘要：

  Crown-annelated quater- (4T) and sexithiophenes (6T) with oligooxyethylene chains of various lengths attached at the 3-positions of the terminal thiophene rings have been synthesized. Analysis of the cation-binding properties of the macrocycles by H-1 NMR and UV-vis spectroscopy reveals the formation of a 1:1 complex with Ba2+, Sr2+, or Pb2+ and shows that cation complexation results in a conformational transition in the pi-conjugated system. Theoretical analysis of this process by density functional methods predicts that this conformational transition results in a narrowing of the highest occupied-lowest unoccupied molecular orbital gap of the conjugated system with a decrease of the redox potentials (E-1(0) and E-2(0)) associated with the formation of the 4T cation radical and dication. Cyclic voltarmmetry shows that, depending on the binding constant, the presence of metal cation produces a negative or a positive shift of E-1(0) while E-2(0) always shifts negatively. This unusual behavior is discussed in terms of interplay between electrostatic interactions and conformational changes associated with cation binding.

  DOI：

  10.1021/ja026819p
• 作为产物：
  描述：

  1,17-diiodo-3,6,9,12,15-pentaoxaheptadecane 、 5,5′-双(三丁基甲锡烷基)-2,2′-二噻吩 、 2-bromo-3-(2-cyanoethylsulfanyl)thiophene 在 cesium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 以26%的产率得到3,3'''-(1,19-dithia-4,7,10,13,15-pentaoxa-1,19-nonadecanediyl)-2,2':5',2'':5'':2'''-quaterthiophene
  参考文献：
  名称：

  Crown-Annelated Oligothiophenes as Model Compounds for Molecular Actuation

  摘要：

  Crown-annelated quater- (4T) and sexithiophenes (6T) with oligooxyethylene chains of various lengths attached at the 3-positions of the terminal thiophene rings have been synthesized. Analysis of the cation-binding properties of the macrocycles by H-1 NMR and UV-vis spectroscopy reveals the formation of a 1:1 complex with Ba2+, Sr2+, or Pb2+ and shows that cation complexation results in a conformational transition in the pi-conjugated system. Theoretical analysis of this process by density functional methods predicts that this conformational transition results in a narrowing of the highest occupied-lowest unoccupied molecular orbital gap of the conjugated system with a decrease of the redox potentials (E-1(0) and E-2(0)) associated with the formation of the 4T cation radical and dication. Cyclic voltarmmetry shows that, depending on the binding constant, the presence of metal cation produces a negative or a positive shift of E-1(0) while E-2(0) always shifts negatively. This unusual behavior is discussed in terms of interplay between electrostatic interactions and conformational changes associated with cation binding.

  DOI：

  10.1021/ja026819p