3'''',4'''-dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2''''':5''''',2'''''':5'''''',2'''''''-octifuran | 1549917-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3'''',4'''-dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2''''':5''''',2'''''':5'''''',2'''''''-octifuran
• 英文别名: 5-[5-[5-(Furan-2-yl)furan-2-yl]furan-2-yl]-2-[5-[5-[5-(furan-2-yl)furan-2-yl]furan-2-yl]-3-hexylfuran-2-yl]-3-hexylfuran；5-[5-[5-(furan-2-yl)furan-2-yl]furan-2-yl]-2-[5-[5-[5-(furan-2-yl)furan-2-yl]furan-2-yl]-3-hexylfuran-2-yl]-3-hexylfuran
• CAS: 1549917-92-1
• 化学式: C₄₄H₄₂O₈
• 分子量: 698.813
• InChiKey: OYXOBTOHBAUUCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'''',4'''-dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2''''':5''''',2'''''':5'''''',2'''''''-octifuran 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 苯 为溶剂， 反应 0.33h， 以83%的产率得到5,5'''''''-dibromo-3'''',4'''-dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2''''':5''''',2'''''':5'''''',2'''''''-octifuran
  参考文献：
  名称：

  Highly Coplanar Very Long Oligo(alkylfuran)s: A Conjugated System with Specific Head-To-Head Defect

  摘要：

  Well-defined monodisperse conjugated oligomers, which have planar backbones and are free from the disturbance of substituents, attract broad interest. Herein, we report a series of symmetrical, isomerically pure oligofurans, namely, the 16-mer 16F-6C(6) together with the related nF-2C(6) (n = 4, 6, 8). Through computational studies and detailed spectroscopic and X-ray characterization, for the first time, we show that the planarity of the furan backbone is almost unaffected by the head-to-head defect which is known to cause considerable twists in its oligo- or polythiophene analogues. We present that the properties of these rigid oligo(alkylfuran)s are strongly influenced by the conjugation length. As the longest monodisperse alpha-oligofuran synthesized to date, 16F-6C(6) was observed to be stable and highly fluorescent. Experimental and computational studies of the redox states of these oligo(alkylfuran)s reveal that 16F-6C(6) has singlet biradical (polaron-pair) character in the doubly oxidized ground state; the open-shell singlet (< S-2 > = 0.989) is 3.8 kcal/mol more stable than the closed-shell dication.

  DOI：

  10.1021/ja411842g
• 作为产物：
  描述：

  3,3′-dibromo-2,2′-bifuran 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 、 甲苯 、 苯 为溶剂， 反应 28.33h， 生成 3'''',4'''-dihexyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2''''':5''''',2'''''':5'''''',2'''''''-octifuran
  参考文献：
  名称：

  Highly Coplanar Very Long Oligo(alkylfuran)s: A Conjugated System with Specific Head-To-Head Defect

  摘要：

  Well-defined monodisperse conjugated oligomers, which have planar backbones and are free from the disturbance of substituents, attract broad interest. Herein, we report a series of symmetrical, isomerically pure oligofurans, namely, the 16-mer 16F-6C(6) together with the related nF-2C(6) (n = 4, 6, 8). Through computational studies and detailed spectroscopic and X-ray characterization, for the first time, we show that the planarity of the furan backbone is almost unaffected by the head-to-head defect which is known to cause considerable twists in its oligo- or polythiophene analogues. We present that the properties of these rigid oligo(alkylfuran)s are strongly influenced by the conjugation length. As the longest monodisperse alpha-oligofuran synthesized to date, 16F-6C(6) was observed to be stable and highly fluorescent. Experimental and computational studies of the redox states of these oligo(alkylfuran)s reveal that 16F-6C(6) has singlet biradical (polaron-pair) character in the doubly oxidized ground state; the open-shell singlet (< S-2 > = 0.989) is 3.8 kcal/mol more stable than the closed-shell dication.

  DOI：

  10.1021/ja411842g