Diethyl 2-amino-5-[(3,4-didecyl-5-formylthiophen-2-yl)methylideneamino]thiophene-3,4-dicarboxylate | 1252598-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Diethyl 2-amino-5-[(3,4-didecyl-5-formylthiophen-2-yl)methylideneamino]thiophene-3,4-dicarboxylate
• CAS: 1252598-47-2
• 化学式: C₃₆H₅₆N₂O₅S₂
• 分子量: 660.983
• InChiKey: YBBLMNXNGNHNHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  45
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  十二烷基伯胺 、 Diethyl 2-amino-5-[(3,4-didecyl-5-formylthiophen-2-yl)methylideneamino]thiophene-3,4-dicarboxylate 在 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 氯仿 为溶剂， 反应 19.0h， 以100%的产率得到
  参考文献：
  名称：

  Selective Chain-End Postpolymerization Reactions and Property Tuning of a Highly Conjugated and All-Thiophene Polyazomethine

  摘要：

  A highly conjugated polyazomethine (3) consisting uniquely of thiophenes was investigated for sustaining postpolymerization property tuning This was courtesy of the ever-present and reactive amino and aldehyde chain ends Subjecting the polymer to polymerization conditions in the absence of monomers resulted in a DPn increase from 15 to 70 The aldehyde chain end was selectively reacted with an aliphatic amine by undergoing reductive amination with sodium triacetoxyborohydride (NaBH(OAc)(3)) while the imines along the conjugated polymer framework remained Intact This illustrates the robustness of the azomethine bond Reductive amination of 3 with a monofunctional amine resulted in selective chain end capping and prevented repolymerization 3 was resistant to dynamic component exchange and monomer shuffling as a result of its high degree of conjugation Conversely chain extension was possible both by reductive amination with an alpha-omega diamine and by reheating the polymer Covalent attachment of two separate segments of 3 was possible by reductive amination with a 2 1 polymer/alpha-omega-diamine stoichiometry This resulted in molecular weight doubling and serves to illustrate the possibility of multiblock tethering via the ever active chain ends Meanwhile, a 1 1 polymer/alpha-omega-diamine stoichiometry gave rise to a polymer with an aliphatic and aromatic amine functionalized at either chain end As a result of the noncomplementary of the two chain ends the polymer could not be repolymerized However, it exhibited consistent molecular weight under various repolymerization reaction conditions indicating the robustness of the heteroconjugated bonds and their tolerance toward dynamic component exchange The color of 3 was also changed from its inherent blue color to green via the covalent attachment of a yellow dansyl derivative by reductive amination at the aldehyde chain end The collective property modification including repolymerization, coblock tethering, color modification, and increased degree of polymerization presenting unequivocal evidence that polyazomethines are capable of undergoing postpolymerization property tailoring

  DOI：

  10.1021/ma102245p