2-[4-(pyrrolidin-1-yl)phenyl]-5-formyl thiophene | 1228958-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-[4-(pyrrolidin-1-yl)phenyl]-5-formyl thiophene
• 英文别名: 2-formyl-5-(4-(pyrrolidin-1-yl)phenyl)thiophene
• CAS: 1228958-79-9
• 化学式: C₁₅H₁₅NOS
• 分子量: 257.356
• InChiKey: ZJHGXZFBVZJAST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[4-(pyrrolidin-1-yl)phenyl]-5-formyl thiophene 、 丙二腈 在 哌啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以42%的产率得到2-((5-(4-(pyrrolidin-1-yl)phenyl)thiophen-2-yl)methylene)malononitrile
  参考文献：
  名称：

  Synthesis and characterization of novel, thermally stable 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5′-dicyanovinyl-2,2′-bithiophenes as potentially promising non-linear optical materials

  摘要：

  Two series of dicyanovinyl-substituted compounds namely 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5'-dicyanovinyl-2,2'-bithiophenes were synthesized through Knoevenagel condensation of the corresponding 2-aryl-5-formyl-thiophenes and 5-aryl-5'-formyl-2,2'-bithiophene precursors. In contrast, the 2-aryl-5-formyl-thiophenes precursor were prepared through the Vilsmeier Haack Arnold reaction starting from inexpensive and easily available precursors such as acetophenones; this method produced the title compounds in higher yield than that recently reported which involved the Suzuki coupling of functionalized aryl boronic acids with 5-bromo-2-formyl-thiophene. Electrochemical studies and characterization of both the linear and non-linear optical properties and thermal properties indicated that good non-linearity was complemented by exceptional thermal stability for some chromophores, making them potential candidates for several optoelectronic applications such as solvatochromic probes and non-linear optical materials. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.01.006
• 作为产物：
  描述：

  氯乙醛 、 β-chloro-β-(4-pyrrolidinophenyl)propenal 在 sodiumsulfide nonahydrate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 5.17h， 以81%的产率得到2-[4-(pyrrolidin-1-yl)phenyl]-5-formyl thiophene
  参考文献：
  名称：

  Synthesis and characterization of novel, thermally stable 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5′-dicyanovinyl-2,2′-bithiophenes as potentially promising non-linear optical materials

  摘要：

  Two series of dicyanovinyl-substituted compounds namely 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5'-dicyanovinyl-2,2'-bithiophenes were synthesized through Knoevenagel condensation of the corresponding 2-aryl-5-formyl-thiophenes and 5-aryl-5'-formyl-2,2'-bithiophene precursors. In contrast, the 2-aryl-5-formyl-thiophenes precursor were prepared through the Vilsmeier Haack Arnold reaction starting from inexpensive and easily available precursors such as acetophenones; this method produced the title compounds in higher yield than that recently reported which involved the Suzuki coupling of functionalized aryl boronic acids with 5-bromo-2-formyl-thiophene. Electrochemical studies and characterization of both the linear and non-linear optical properties and thermal properties indicated that good non-linearity was complemented by exceptional thermal stability for some chromophores, making them potential candidates for several optoelectronic applications such as solvatochromic probes and non-linear optical materials. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.01.006

文献信息

• Synthesis of multi-donor dyes and influence of molecular design on dye-sensitized solar cells
  作者：Ashok Keerthi、Ming Hui Chua、Thuang Yuan Timothy Chan、Yeru Liu、Qing Wang、Suresh Valiyaveettil

  DOI：10.1039/c6ra08530j

  日期：——

  Multi-donor incorporated organic dyes were designed and synthesized and their structure–property relationship was investigated in dye-sensitized solar cells (DSCs). Five N,N-disubstituted aniline donor groups along with carbazole and thiophene secondary donors were combined into the (D)n–π–A design with cyanoacrylic acid as the acceptor. The dyes showed broad absorption bands with absorption maxima

  设计并合成了多供体有机染料，并在染料敏化太阳能电池（DSC）中研究了它们的结构与性质之间的关系。五个N，N-二取代的苯胺供体基团以及咔唑和噻吩的次级供体基团以氰基丙烯酸为受体结合到（D）n - π -A设计中。染料显示出宽的吸收带，最大吸收在470–485 nm范围内，光学带隙约为1.94–2.37 eV。我们的结果表明，将庞大的基团和弯曲类型的架构结合在一起有助于改善DSC的性能。