diethyl 2-((1-methyl-1H-pyrrol-2-yl)methyleneamino)-5-((thiophen-2-yl)methyleneamino)thiophene-3,4-dicarboxylate | 1151680-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 2-((1-methyl-1H-pyrrol-2-yl)methyleneamino)-5-((thiophen-2-yl)methyleneamino)thiophene-3,4-dicarboxylate
• 英文别名: Diethyl 2-[(1-methyl-1H-pyrrol-2-yl)methyleneamino]-5-(2-thienylmethyleneamino)thiophene-3,4-dicarboxylate；diethyl 2-[(E)-(1-methylpyrrol-2-yl)methylideneamino]-5-[(E)-thiophen-2-ylmethylideneamino]thiophene-3,4-dicarboxylate
• CAS: 1151680-47-5
• 化学式: C₂₁H₂₁N₃O₄S₂
• 分子量: 443.547
• InChiKey: ZDHQEIHSCBVUSG-FWSOMWAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-amino-5-[(thiophen-2-ylmethylene)amino]thiophene-3,4-dicarboxylic acid diethyl ester 、 N-甲基-2-吡咯甲醛 在 三乙烯二胺 、 四氯化钛 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以50%的产率得到diethyl 2-((1-methyl-1H-pyrrol-2-yl)methyleneamino)-5-((thiophen-2-yl)methyleneamino)thiophene-3,4-dicarboxylate
  参考文献：
  名称：

  Unsymmetric Pyrrole, Thiophene, and Furan-Conjugated Comonomers Prepared Using Azomethine Connections: Potential New Monomers for Alternating Homocoupled Products

  摘要：

  Unsymmetric comonomers consisting of thiophene, pyrrole, and furan heterocycles were prepared using azomethine bonds. Photophysical investigation of the novel pi-donor-donor-donor segmented compounds revealed that their singlet excited state is only partially deactivated by internal conversion unlike their all-thiophene azomethine analogues. Temperature-dependent steady-state and time-resolved emission studies demonstrated that the unsymmetric compounds deactivated efficiently their singlet excited state by intersystem crossing to populate the triplet manifold. This lower energy state is rapidly deactivated by nonradiative self-quenching. The comonomers and their anodically prepared conjugated homocoupled products are both electrochemically active, resulting in new compounds that can be mutually oxidized and reduced. Meanwhile, the oxidation potentials of the coupled products are shifted by up to 400 mV to more cathodic potentials relative to their corresponding comonomers, confirming their increased degree of conjugation.

  DOI：

  10.1021/jo8002503