3,3'-dihexyl-2,2'-bifuran | 1549916-31-5

• 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: 3,3'-dihexyl-2,2'-bifuran
• CAS: 1549916-31-5
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: RVMREPQMCNQZPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  26.28
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,3'-dihexyl-2,2'-bifuran 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 苯 为溶剂， 反应 22.66h， 生成 2-(tributylstannyl)-3'',4'-dihexyl-2,2':5',2'':5'',2'''-quaterfuran
  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 、 己基溴化镁 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 为溶剂， 反应 10.0h， 以77%的产率得到3,3'-dihexyl-2,2'-bifuran
  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