2,2,6,6-Tetrabutyl-4,8-bis[2-(2,5-dimethoxyphenyl)ethynyl]-[1,3]dithiolo[4,5-f][1,3]benzodithiole | 1225230-45-4

• 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: 2,2,6,6-Tetrabutyl-4,8-bis[2-(2,5-dimethoxyphenyl)ethynyl]-[1,3]dithiolo[4,5-f][1,3]benzodithiole
• 英文别名: 2,2,6,6-tetrabutyl-4,8-bis[2-(2,5-dimethoxyphenyl)ethynyl]-[1,3]dithiolo[4,5-f][1,3]benzodithiole
• CAS: 1225230-45-4
• 化学式: C₄₄H₅₄O₄S₄
• 分子量: 775.174
• InChiKey: XZWOONJVSSVCHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2,6,6-Tetrabutyl-4,8-bis[2-(2,5-dimethoxyphenyl)ethynyl]-[1,3]dithiolo[4,5-f][1,3]benzodithiole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以60%的产率得到
  参考文献：
  名称：

  Conjugated Polymers That Respond to Oxidation with Increased Emission

  摘要：

  Thioether-containing poly(para-phenylene-ethynylene) (PPE) copolymers show a strong fluorescence turn-on response when exposed to oxidants in solution as a result of the selective conversion of thioether substituents into sulfoxides and sulfones. We propose that the increase in fluorescence quantum yield (Phi(F)) upon oxidation is the result of both an increase in the rate of fluorescence (k(F)), as a result of greater spatial overlap of the frontier molecular orbitals in the oxidized materials, and an increase in the fluorescence lifetime (tau(F)), due to a decrease in the rate of nonradiative decay. Contrary to established literature, the reported sulfoxides do not always act as fluorescence quenchers. The oxidation is accompanied by spectral changes in the absorption and emission of the polymers, which are dramatic when oxidation causes the copolymer to acquire a donor-acceptor interaction. The oxidized polymers have high fluorescence quantum yields in the solid state, with some having increased photostability. A turn-on fluorescence response to hydrogen peroxide in organic solvents in the presence of an oxidation catalyst indicates the potential of thioether-containing materials for oxidant sensing. The reported polymers show promise as new materials in applications where photostability is important, where tunability of emission across the visible spectrum is desired, and where efficient emission is an advantage.

  DOI：

  10.1021/ja1019063
• 作为产物：
  描述：

  2,2,6,6-tetra-n-butyl-4,8-diiodobenzo[1,2-d;4,5-d']bis[1,3]dithiole 、 2-ethynyl-1,4-dimethoxybenzene 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 甲苯 为溶剂， 以67%的产率得到2,2,6,6-Tetrabutyl-4,8-bis[2-(2,5-dimethoxyphenyl)ethynyl]-[1,3]dithiolo[4,5-f][1,3]benzodithiole
  参考文献：
  名称：

  Conjugated Polymers That Respond to Oxidation with Increased Emission

  摘要：

  Thioether-containing poly(para-phenylene-ethynylene) (PPE) copolymers show a strong fluorescence turn-on response when exposed to oxidants in solution as a result of the selective conversion of thioether substituents into sulfoxides and sulfones. We propose that the increase in fluorescence quantum yield (Phi(F)) upon oxidation is the result of both an increase in the rate of fluorescence (k(F)), as a result of greater spatial overlap of the frontier molecular orbitals in the oxidized materials, and an increase in the fluorescence lifetime (tau(F)), due to a decrease in the rate of nonradiative decay. Contrary to established literature, the reported sulfoxides do not always act as fluorescence quenchers. The oxidation is accompanied by spectral changes in the absorption and emission of the polymers, which are dramatic when oxidation causes the copolymer to acquire a donor-acceptor interaction. The oxidized polymers have high fluorescence quantum yields in the solid state, with some having increased photostability. A turn-on fluorescence response to hydrogen peroxide in organic solvents in the presence of an oxidation catalyst indicates the potential of thioether-containing materials for oxidant sensing. The reported polymers show promise as new materials in applications where photostability is important, where tunability of emission across the visible spectrum is desired, and where efficient emission is an advantage.

  DOI：

  10.1021/ja1019063