3H-imidazole-4-carbodithioic acid 4-vinylbenzyl ester | 855596-27-9

• 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: 3H-imidazole-4-carbodithioic acid 4-vinylbenzyl ester
• 英文别名: (4-vinylbenzyl) 1H-imidazole-5-carbodithioate；(4-ethenylphenyl)methyl 1H-imidazole-5-carbodithioate
• CAS: 855596-27-9
• 化学式: C₁₃H₁₂N₂S₂
• 分子量: 260.384
• InChiKey: FHNLIJHOPSYOJM-UHFFFAOYSA-N

物化性质

• 沸点：
  498.2±47.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯甲基苯乙烯 、 4⁽⁵⁾-imidazoledithiocarboxylic acid 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 以22.8%的产率得到3H-imidazole-4-carbodithioic acid 4-vinylbenzyl ester
  参考文献：
  名称：

  Highly Branched Poly(N-isopropylacrylamide)s with Imidazole End Groups Prepared by Radical Polymerization in the Presence of a Styryl Monomer Containing a Dithioester Group

  摘要：

  Highly branched poly(N-isopropylacrylamide) (PNIPAM) compounds were prepared by copolymerization of 3H-imidazole-4-carbodithioic acid 4-vinylbenzyl ester, 1, with N-isopropylacrylamide (NIPAM) using reversible addition-fragmentation chain transfer (RAFT) polymerization. The polymerizations proceeded well with few side reactions. An increase in the content of 1 in the monomer feed appears to increase the number of branch chains, and at the same time no evidence was obtained for the presence of substituted acrylamide chain ends that may potentially result via elimination of the dithioate group. The polymer products show a clear tendency to increased molecular weight as the extent of conversion of monomer increases, while size exclusion chromatography (SEC) profiles indicate a complex distribution of molecular weights compared to linear polymers obtained with a non-RAFT carboxylate monomer. Both NMR and viscometry indicate that, as expected, increasing the amount of I in the feed has the effect of increasing the degree of branching in the final product. This increase in branching reduces the intrinsic viscosity of the solutions of the highly branched polymers compared to similar linear polymers. Poly(N-isopropylacrylamide) displays a lower critical solution temperature (LCST) in aqueous solutions, and cloud point data indicate a clear effect of chain architecture on the temperature at which this transition occurs. Thus, a set of linear analogous copolymers have LCST's that, for equivalent mole fractions of imidazole content, are higher than the similar highly branched polymers. However, on complexation of copper by the imidazole groups the LCSTs of the linear and highly branched sets cannot be differentiated.

  DOI：

  10.1021/ma047742n

文献信息

• Structural optimization of highly branched thermally responsive polymers as a means of controlling transition temperature
  作者：Kai Chang、Nathan C. Rubright、Patti D. Lowery、Lakeshia J. Taite

  DOI：10.1002/pola.26596

  日期：2013.5.1

  Highly branched “smart” polymers have emerged as a unique class of polymers with wide‐ranging applications. Poly(N‐isopropylacrylamide) (pNIPAAm) is at the forefront of stimuli‐responsive polymers; however, few transition temperature‐modification methods of linear pNIPAAm have been explored in highly branched systems. In this study, the three primary techniques of transition temperature modification

  高度支化的“智能”聚合物已成为一类独特的聚合物，具有广泛的应用范围。聚（N-异丙基丙烯酰胺）（pNIPAAm）处于刺激反应性聚合物的最前沿；然而，在高度分支的系统中，很少研究线性pNIPAAm的转变温度修饰方法。在这项研究中，研究了线性pNIPAAm的三种转变温度改性的主要技术对高支化聚合物的功效。在这些技术中，助溶剂介导的立构规整控制显示出与预期相反的效果。尽管高度支化的体系每个聚合物具有更多的端基，但通过末端基团的改性进行的温度变化控制显示出在高度支化的体系中功效显着下降。与线性类似物相比，与亲水性共聚单体的共聚表现出不同的功效变化，从而洞悉了对共聚物周围结构化水的特定影响。虽然共聚在改变转变温度方面被证明是最通用的，但所有技术均显示出有趣的次要效果。©2013 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2013年
• Highly Branched Poly(<i>N</i>-isopropylacrylamide)s with Imidazole End Groups Prepared by Radical Polymerization in the Presence of a Styryl Monomer Containing a Dithioester Group
  作者：Steven Carter、Barry Hunt、Stephen Rimmer

  DOI：10.1021/ma047742n

  日期：2005.5.1

  Highly branched poly(N-isopropylacrylamide) (PNIPAM) compounds were prepared by copolymerization of 3H-imidazole-4-carbodithioic acid 4-vinylbenzyl ester, 1, with N-isopropylacrylamide (NIPAM) using reversible addition-fragmentation chain transfer (RAFT) polymerization. The polymerizations proceeded well with few side reactions. An increase in the content of 1 in the monomer feed appears to increase the number of branch chains, and at the same time no evidence was obtained for the presence of substituted acrylamide chain ends that may potentially result via elimination of the dithioate group. The polymer products show a clear tendency to increased molecular weight as the extent of conversion of monomer increases, while size exclusion chromatography (SEC) profiles indicate a complex distribution of molecular weights compared to linear polymers obtained with a non-RAFT carboxylate monomer. Both NMR and viscometry indicate that, as expected, increasing the amount of I in the feed has the effect of increasing the degree of branching in the final product. This increase in branching reduces the intrinsic viscosity of the solutions of the highly branched polymers compared to similar linear polymers. Poly(N-isopropylacrylamide) displays a lower critical solution temperature (LCST) in aqueous solutions, and cloud point data indicate a clear effect of chain architecture on the temperature at which this transition occurs. Thus, a set of linear analogous copolymers have LCST's that, for equivalent mole fractions of imidazole content, are higher than the similar highly branched polymers. However, on complexation of copper by the imidazole groups the LCSTs of the linear and highly branched sets cannot be differentiated.