1,4-bis(3,6-diethylcarbazol-9-yl)butane | 189066-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,4-bis(3,6-diethylcarbazol-9-yl)butane
• 英文别名: 9,9'-(Butane-1,4-diyl)bis(3,6-diethyl-9H-carbazole)；9-[4-(3,6-diethylcarbazol-9-yl)butyl]-3,6-diethylcarbazole
• CAS: 189066-40-8
• 化学式: C₃₆H₄₀N₂
• 分子量: 500.727
• InChiKey: ZVBOGLUHIKMMAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3,6-diacetylcarbazole 在 盐酸 、 mercury dichloride 、 potassium hydroxide 、 锌 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 16.0h， 生成 1,4-bis(3,6-diethylcarbazol-9-yl)butane
  参考文献：
  名称：

  Synthesis and charge-transfer complex formations of 1,n-bis(3,6-diethylcarbazol-9-yl)alkanes with three π-acceptors

  摘要：

  Dimeric 1,n-bis(3,6-diethylcarbazol-9-yl)alkanes (where n = 1-5) were synthesized and their structures were characterized via spectroscopic techniques. Structures of two of the dimers, 1,2-bis(3,6-diethylcarbazol-9-yl)ethane (2b) and 1,4-bis(3,6-diethylcarbazol-9-yl)butane (2d), were investigated by single crystal X-ray crystallographic techniques. The crystal structures of 2b and 2d were solved in the monoclinic space groups C2/c and P2(1)/n, respectively. The methylene chain adopted an anti conformation in 2b and a gauche-anti-gauche conformation in 2d, enabling coplanar orientations of carbazole rings in both structures. The molecular packing in both structures was stabilized by intermolecular pi-pi stacking. Charge transfer complexations of 2a-2e with the pi-acceptors p-chloranil, tetracyanoethylene, and tetracyanoquinodimethane in solution were investigated by determining their stoichiometries, molar absorptivities, equilibrium constants, enthalpies, and entropies. All the dimers formed weakly associated complexes with each of the acceptors having equilibrium constants between 1.32-8.94 M-1 in 1,2-dichloroethane. Complexations were driven by the slightly negative formation enthalpies between -2.00 and -4.24 kcal mol(-1). (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.02.026

文献信息

• Synthesis and charge-transfer complex formations of 1,n-bis(3,6-diethylcarbazol-9-yl)alkanes with three π-acceptors
  作者：Erol Asker、Fahrettin Filiz

  DOI：10.1016/j.molstruc.2013.02.026

  日期：2013.5

  Dimeric 1,n-bis(3,6-diethylcarbazol-9-yl)alkanes (where n = 1-5) were synthesized and their structures were characterized via spectroscopic techniques. Structures of two of the dimers, 1,2-bis(3,6-diethylcarbazol-9-yl)ethane (2b) and 1,4-bis(3,6-diethylcarbazol-9-yl)butane (2d), were investigated by single crystal X-ray crystallographic techniques. The crystal structures of 2b and 2d were solved in the monoclinic space groups C2/c and P2(1)/n, respectively. The methylene chain adopted an anti conformation in 2b and a gauche-anti-gauche conformation in 2d, enabling coplanar orientations of carbazole rings in both structures. The molecular packing in both structures was stabilized by intermolecular pi-pi stacking. Charge transfer complexations of 2a-2e with the pi-acceptors p-chloranil, tetracyanoethylene, and tetracyanoquinodimethane in solution were investigated by determining their stoichiometries, molar absorptivities, equilibrium constants, enthalpies, and entropies. All the dimers formed weakly associated complexes with each of the acceptors having equilibrium constants between 1.32-8.94 M-1 in 1,2-dichloroethane. Complexations were driven by the slightly negative formation enthalpies between -2.00 and -4.24 kcal mol(-1). (C) 2013 Elsevier B.V. All rights reserved.