2,4-Diamino-6-di(2-ethylhexyl)amino-1,3,5-triazine | 154948-55-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,4-Diamino-6-di(2-ethylhexyl)amino-1,3,5-triazine
• 英文别名: N~2~,N~2~-Bis(2-ethylhexyl)-1,3,5-triazine-2,4,6-triamine；2-N,2-N-bis(2-ethylhexyl)-1,3,5-triazine-2,4,6-triamine
• CAS: 154948-55-7
• 化学式: C₁₉H₃₈N₆
• 分子量: 350.551
• InChiKey: ANCYKCBMVRGHGY-UHFFFAOYSA-N

物化性质

• 沸点：
  522.1±33.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  94
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-Diamino-6-di(2-ethylhexyl)amino-1,3,5-triazine 、 5-(5-dibutylaminothiophene-2-ylmethylidene)-4-nonyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile 以 氘代氯仿 为溶剂， 生成 5-(5-dibutylamino-thiophen-2-ylmethylene)-4-nonyl-2,6-dioxo-1,2,5,6-tetrahydro-pyridine-3-carbonitrile; compound with N,N-bis-(2-ethyl-hexyl)-[1,3,5]triazine-2,4,6-triamine
  参考文献：
  名称：

  含酰亚胺官能团的花青染料：氢与三聚氰胺受体的键合反应及其研究。

  摘要：

  CH酸性杂环4-烷基-2,6-二氧-1,2,5,6-四氢吡啶-3-腈（5a和b）和巴比妥酸（15）与富电子的噻吩醛和苯甲醛衍生物的缩合反应分别得到一甲亚胺染料10-13和17-19。5a，b和15与N，N′-二苯基甲idine或二丁基甲酰胺在乙酸酐中甲酰化，并与4-吡啶鎓盐9a，b进一步反应，得到二甲胺染料14和20a，b。已通过三聚氰胺21的NMR滴定实验研究了花青染料10-14的酰亚胺基团的三氢键。 。这些结果可以通过半经验计算来合理化，该计算揭示了在末端双键的给电子性碳环或杂环基团发生变化时，参与氢键结合的氧官能团上电荷密度的微小变化。尽管在氯仿中酰亚胺和三聚氰胺之间三氢键的结合常数相当弱，但事实证明它们足够强，可以通过与两亲三聚氰胺和偶极聚集的配位来促进其中某些染料在脂族溶剂中的溶解。在甲基环己烷与氯仿中观察到的紫外可见光谱变化表明，通过非共价聚合形成了胶体组装体。

  DOI：

  10.1021/jo0351670
• 作为产物：
  描述：

  2-氨基-4,6-二氯-S-三嗪 、 二异辛胺 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以58%的产率得到2,4-Diamino-6-di(2-ethylhexyl)amino-1,3,5-triazine
  参考文献：
  名称：

  Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures

  摘要：

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.

  DOI：

  10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

文献信息

• Hierarchical Self-Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures
  作者：Frank Würthner、Christoph Thalacker、Armin Sautter、Wolfgang Schärtl、Wolfram Ibach、Olaf Hollricher

  DOI：10.1002/1521-3765(20001103)6:21<3871::aid-chem3871>3.3.co;2-w

  日期：2000.11.3

  A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3.8)(n), are discussed, and a general formula to estimate the chain length of [AA - BB](n) nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, pi-pi interactions were observed for perylene bisimide - melamine assemblies 3b.8b and 3b.8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and pi-pi interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano- to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.
• Merocyanine Dyes Containing Imide Functional Groups:  Synthesis and Studies on Hydrogen Bonding to Melamine Receptors
  作者：Frank Würthner、Sheng Yao

  DOI：10.1021/jo0351670

  日期：2003.11.1

  changes in the charge density at the oxygen functionalities involved in hydrogen bonding upon variation of the electron-donating carbocyclic or heterocyclic groups at the terminal double bond. Although the binding constants for triple hydrogen bonding between imides and melamines are rather weak in chloroform, they proved to be strong enough to facilitate dissolution of some of these dyes in aliphatic solvents

  CH酸性杂环4-烷基-2,6-二氧-1,2,5,6-四氢吡啶-3-腈（5a和b）和巴比妥酸（15）与富电子的噻吩醛和苯甲醛衍生物的缩合反应分别得到一甲亚胺染料10-13和17-19。5a，b和15与N，N′-二苯基甲idine或二丁基甲酰胺在乙酸酐中甲酰化，并与4-吡啶鎓盐9a，b进一步反应，得到二甲胺染料14和20a，b。已通过三聚氰胺21的NMR滴定实验研究了花青染料10-14的酰亚胺基团的三氢键。 。这些结果可以通过半经验计算来合理化，该计算揭示了在末端双键的给电子性碳环或杂环基团发生变化时，参与氢键结合的氧官能团上电荷密度的微小变化。尽管在氯仿中酰亚胺和三聚氰胺之间三氢键的结合常数相当弱，但事实证明它们足够强，可以通过与两亲三聚氰胺和偶极聚集的配位来促进其中某些染料在脂族溶剂中的溶解。在甲基环己烷与氯仿中观察到的紫外可见光谱变化表明，通过非共价聚合形成了胶体组装体。