N-{2-[(4-氯-3-氰基-5-甲酰基-2-噻吩基)偶氮]-5-(二乙基氨基)苯基}乙酰胺 | 104366-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-{2-[(4-氯-3-氰基-5-甲酰基-2-噻吩基)偶氮]-5-(二乙基氨基)苯基}乙酰胺
• 中文别名: 2'-(4-氯-3-氰基-5-甲酰基-2-噻嗯基)偶氮-5'-二乙胺基乙酰苯胺
• 英文名称: N,N-diethyl-3-acetamido-4-[(5-formyl-4-chloro-3-cyano-2-thienyl)azo]benzeneamine
• 英文别名: 2'-(4-Chloro-3-cyano-5-formyl-2-thienyl)azo-5'-diethylaminoacetanilide；N-[2-[(4-chloro-3-cyano-5-formylthiophen-2-yl)diazenyl]-5-(diethylamino)phenyl]acetamide
• CAS: 104366-25-8
• 化学式: C₁₈H₁₈ClN₅O₂S
• 分子量: 403.892
• InChiKey: LEIMRDFPISBEPH-UHFFFAOYSA-N

物化性质

• 沸点：
  679.5±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24,S37
• 危险类别码：
  R43

反应信息

• 作为反应物：
  描述：

  N-{2-[(4-氯-3-氰基-5-甲酰基-2-噻吩基)偶氮]-5-(二乙基氨基)苯基}乙酰胺 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以63%的产率得到N,N-diethyl-3-acetamido-4-[(5-hydroxymethyl-4-chloro-3-cyano-2-thienyl)azo]benzeneamine
  参考文献：
  名称：

  Synthesis and photoelectrochemical properties of a fullerene–azothiophene dyad

  摘要：

  In this paper we describe the synthesis, electrochemistry and photophysical behavior of a fullerene-based donor–acceptor dyad (2) in which the donor unit is an azothiophene dye. Dyad 2, prepared in one step starting from C60, commercially available N-methylglycine and thienylazobenzeneamine 1, can be selectively excited in the visible region where the dye has an absorption maximum at 567 nm. Implementation of electrochemical and photophysical data reveals that both intramolecular energy- and electron-transfer are thermodynamically feasible processes. Steady-state luminescence of dyad 2 in CH2Cl2 shows a quenching of the dye singlet excited state (1dye*) and evidence of the fullerene singlet excited state (1C60*) emission. Flash-photolytic experiments, on the other hand, exhibit characteristic differential absorption changes attributed to the C60·––dye·+ charge-separated state. Interestingly, it has been estimated that the energy difference between 1C60* and the charge separated state is very small, leading to the hypothesis that a rapid exchange between the two states occurs. Sensitization of TiO2 with dyad 2 and model compound 3 is also reported and discussed.

  DOI：

  10.1039/a905287i

文献信息

• Synthesis and photoelectrochemical properties of a fullerene–azothiophene dyad
  作者：Sandro Cattarin、Paola Ceroni、Dirk M. Guldi、Michele Maggini、Enzo Menna、Francesco Paolucci、Sergio Roffia、Gianfranco Scorrano

  DOI：10.1039/a905287i

  日期：——

  In this paper we describe the synthesis, electrochemistry and photophysical behavior of a fullerene-based donor–acceptor dyad (2) in which the donor unit is an azothiophene dye. Dyad 2, prepared in one step starting from C60, commercially available N-methylglycine and thienylazobenzeneamine 1, can be selectively excited in the visible region where the dye has an absorption maximum at 567 nm. Implementation of electrochemical and photophysical data reveals that both intramolecular energy- and electron-transfer are thermodynamically feasible processes. Steady-state luminescence of dyad 2 in CH2Cl2 shows a quenching of the dye singlet excited state (1dye*) and evidence of the fullerene singlet excited state (1C60*) emission. Flash-photolytic experiments, on the other hand, exhibit characteristic differential absorption changes attributed to the C60·––dye·+ charge-separated state. Interestingly, it has been estimated that the energy difference between 1C60* and the charge separated state is very small, leading to the hypothesis that a rapid exchange between the two states occurs. Sensitization of TiO2 with dyad 2 and model compound 3 is also reported and discussed.