Bis[6-[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]hexyl] propanedioate | 1351165-90-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Bis[6-[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]hexyl] propanedioate
• 英文别名: bis[6-[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]hexyl] propanedioate
• CAS: 1351165-90-6
• 化学式: C₃₁H₃₆N₄O₆S₂
• 分子量: 624.782
• InChiKey: VIMVEXBAJWPNHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  43
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  181
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Bis[6-[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]hexyl] propanedioate 、 足球烯 在 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以42%的产率得到
  参考文献：
  名称：

  Synthesis of [60]fullerene derivatives bearing five-membered heterocyclic wings and an investigation of their photophysical kinetic properties

  摘要：

  The preparation, characterization and photophysical properties of six new stable [6,6]-closed fullerene cycloadducts bearing five-membered heterocycles are described. The modified [60]fullerenes are obtained by a simple and rapid synthesis via a Bingel-type reaction with tetrazole and oxadiazole malonate derivatives. The photophysical kinetics of these new fullerene derivatives in toluene solution under ultraviolet illumination (375 nm, UVA) are studied by electron paramagnetic resonance and free-radical spin-trapping using alpha-phenyl-N-tert-butyl nitrone as a spin-trap. The results are compared with pure [60]fullerene and [6,6]-phenyl C-61 butyric acid methyl ester (C-60-PCBM). It is concluded that for all six new compounds as well as pure [60]fullerene and PCBM both superoxide and singlet oxygen are produced in the first stages of UVA illumination following the type I and II mechanisms, respectively. In all cases singlet oxygen is produced as the primary dominant species; however, the type I mechanism always occurs in parallel with type II. In the end, the superoxide is self-dismuted into hydroxyl radicals, thus yielding PBN-OH center dot spin adducts (g = 2.007 and a(hf) (N-14) = 1.54 mT). The kinetic reaction constants and their efficiencies in the production of reactive oxygen species at 375 nm and per mW of absorbed power are determined. The experimental results are consistent with an autocatalytic reaction model in which the system evolutes under UVA illumination, with superoxide catalyzing the conversion of singlet oxygen into more superoxide. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.10.007
• 作为产物：
  描述：

  6-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)hexan-1-ol 、 丙二酰氯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以60%的产率得到Bis[6-[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]hexyl] propanedioate
  参考文献：
  名称：

  Synthesis of [60]fullerene derivatives bearing five-membered heterocyclic wings and an investigation of their photophysical kinetic properties

  摘要：

  The preparation, characterization and photophysical properties of six new stable [6,6]-closed fullerene cycloadducts bearing five-membered heterocycles are described. The modified [60]fullerenes are obtained by a simple and rapid synthesis via a Bingel-type reaction with tetrazole and oxadiazole malonate derivatives. The photophysical kinetics of these new fullerene derivatives in toluene solution under ultraviolet illumination (375 nm, UVA) are studied by electron paramagnetic resonance and free-radical spin-trapping using alpha-phenyl-N-tert-butyl nitrone as a spin-trap. The results are compared with pure [60]fullerene and [6,6]-phenyl C-61 butyric acid methyl ester (C-60-PCBM). It is concluded that for all six new compounds as well as pure [60]fullerene and PCBM both superoxide and singlet oxygen are produced in the first stages of UVA illumination following the type I and II mechanisms, respectively. In all cases singlet oxygen is produced as the primary dominant species; however, the type I mechanism always occurs in parallel with type II. In the end, the superoxide is self-dismuted into hydroxyl radicals, thus yielding PBN-OH center dot spin adducts (g = 2.007 and a(hf) (N-14) = 1.54 mT). The kinetic reaction constants and their efficiencies in the production of reactive oxygen species at 375 nm and per mW of absorbed power are determined. The experimental results are consistent with an autocatalytic reaction model in which the system evolutes under UVA illumination, with superoxide catalyzing the conversion of singlet oxygen into more superoxide. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.10.007

文献信息

• Synthesis of [60]fullerene derivatives bearing five-membered heterocyclic wings and an investigation of their photophysical kinetic properties
  作者：Leandro J. Santos、Ana S.P. Gonçalves、Klaus Krambrock、Maurício V.B. Pinheiro、Marcos N. Eberlin、Boniek G. Vaz、Rossimiriam P. de Freitas、Rosemeire B. Alves

  DOI：10.1016/j.jphotochem.2010.10.007

  日期：2011.1

  The preparation, characterization and photophysical properties of six new stable [6,6]-closed fullerene cycloadducts bearing five-membered heterocycles are described. The modified [60]fullerenes are obtained by a simple and rapid synthesis via a Bingel-type reaction with tetrazole and oxadiazole malonate derivatives. The photophysical kinetics of these new fullerene derivatives in toluene solution under ultraviolet illumination (375 nm, UVA) are studied by electron paramagnetic resonance and free-radical spin-trapping using alpha-phenyl-N-tert-butyl nitrone as a spin-trap. The results are compared with pure [60]fullerene and [6,6]-phenyl C-61 butyric acid methyl ester (C-60-PCBM). It is concluded that for all six new compounds as well as pure [60]fullerene and PCBM both superoxide and singlet oxygen are produced in the first stages of UVA illumination following the type I and II mechanisms, respectively. In all cases singlet oxygen is produced as the primary dominant species; however, the type I mechanism always occurs in parallel with type II. In the end, the superoxide is self-dismuted into hydroxyl radicals, thus yielding PBN-OH center dot spin adducts (g = 2.007 and a(hf) (N-14) = 1.54 mT). The kinetic reaction constants and their efficiencies in the production of reactive oxygen species at 375 nm and per mW of absorbed power are determined. The experimental results are consistent with an autocatalytic reaction model in which the system evolutes under UVA illumination, with superoxide catalyzing the conversion of singlet oxygen into more superoxide. (C) 2010 Elsevier B.V. All rights reserved.