3',5'-bis-pentafluorosulfanyl-biphenyl-2,3-dicarbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3',5'-bis-pentafluorosulfanyl-biphenyl-2,3-dicarbonitrile
• 英文别名: 3',5'-bis-pentafluorosulfanylbiphenyl-2,3-dicarbonitrile；3-[3,5-Bis(pentafluoro-lambda6-sulfanyl)phenyl]benzene-1,2-dicarbonitrile；3-[3,5-bis(pentafluoro-λ6-sulfanyl)phenyl]benzene-1,2-dicarbonitrile
• 化学式: C₁₄H₆F₁₀N₂S₂
• 分子量: 456.331
• InChiKey: PIHKOCPVEQPCHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3',5'-bis-pentafluorosulfanyl-biphenyl-2,3-dicarbonitrile 、 三氯化硼 以 对二甲苯 为溶剂， 反应 6.0h， 以15%的产率得到chloro-[1,8,15-tris(3',5'-bis-pentafluorosulfanylphenyl)-subphthalocyaninato]boron (III)
  参考文献：
  名称：

  Pentafluorosulfanyl (SF5) in dyes: C3-Regioselective synthesis of α-mono-substituted subphthalocyanine with SF5-phenyl group

  摘要：

  Pentafluorosulfanyl (SF5) is a unique fluorinated functional group. It has high lipophilicity and electronegativity, and is chemically and thermally stable. In addition, the steric hindrance of SF5 is larger than that of the trifluoromethyl (CF3) group. Therefore the introduction of SF5 group into functional dyes such as phthalocyanines and subphthalocyanines should be an attractive strategy to improve their robustness and alter their optical property. We attempted the C-3-regioselective cyclotrimerization of aryl-substituted phthalonitriles 3 to provide subphthalocyanines (SubPcs) 1. alpha-Mono-substituted SubPc la was C-3-regioselectively synthesized by introducing a bis(SF5)Ph group on the alpha-peripheral position providing 1a as a single isomer. The effect of the SF5 group on the synthesis and optical property of SubPcs were investigated by comparing with the H and CF3 analogues, 1b and 1c. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.08.016
• 作为产物：
  描述：

  1,3-二(五氟硫基)-5-溴苯 在 potassium phosphate 、 异丙基溴化镁 、 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.5h， 生成 3',5'-bis-pentafluorosulfanyl-biphenyl-2,3-dicarbonitrile
  参考文献：
  名称：

  Synthesis and property of novel phthalocyanine having a 3,5-bis-pentafluorosulfanylphenyl group on the α-peripheral position

  摘要：

  The pentafluorosulfanyl (SF5) group is bulky, highly lipophilic, highly electronegative, and highly stable. Despite the potential use of SF5-containing phthalocyanines, no example exists. We herein report the synthesis of 3,5-bis-pentafluorosulfanylphenyl ((SF5)(2)Ph)-Substituted phthalocyanine onto the alpha-peripheral position for the first time. Regioselective synthesis was possible by the effect of the SF5 moiety via macrocyclization. The synthesis of phthalocyanines with CF3 and H instead of SF5 was also carried out in order to investigate the effect of SF5. Phthalocyanines were compared using UV/Vis spectra. Phthalocyanine with SF5 exists free from aggregation and protonation in dichloromethane solution. The two planes of 3,5-(SF5)(2)Ph and parent Pc ring in space are nearly perpendicular at which they meet is a right angle, while the two planes of CF3 analogue in space are not. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.09.012