溶剂模板和卤素键定向组装合成[2+2]席夫碱大环

IF 2.3 4区 化学 Q2 Agricultural and Biological Sciences Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2022-03-31 DOI:10.1007/s10847-022-01137-2
Chloe M. Taylor, Nathan L. Kilah
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引用次数: 1

摘要

希夫碱亚胺缩合反应是大环合成和超分子化学研究的重要手段。在这里,我们讨论了使用二羰基杂环和二胺的无模板合成可能产生的产物混合物,并寻求开发用于选择性大环形成的无金属模板方法。在标准文献条件下,一系列烷基α,ω-二胺与邻菲罗啉和吡啶类杂环二乙醛结合。对反应条件进行了改进,以证明溶剂的选择与产物平衡之间的关系。据观察,苯和甲苯可以使产物和未反应起始物质的混合物在许多体系中主要形成一种亚胺产物。一旦在选定的溶剂中对大环产物进行了表征,就可以使用非共价相互作用将碘化卤素键客体分子添加到直接的大环组装中。研究了主客体适宜性和卤素键相互作用,发现四乙烯对菲罗啉基大环的形成有影响。通过概念验证实验证明了客体分子四乙烯对竞争动态组合化学条件下形成的大环产物的影响。
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Synthesis of [2+2] Schiff base macrocycles by a solvent templating strategy and halogen bonding directed assembly

Schiff base imine condensations are a useful tool for macrocycle synthesis and applications within supramolecular chemistry. Here we address the mixtures of products that can arise from template free synthesis using dicarbonylheterocycles and diamines, and look to develop metal-free template methods for selective macrocycle formation. A range of alkyl α,ω-diamines were combined with phenanthroline and pyridine heterocyclic dicarbaldehydes under standard literature conditions. The reaction conditions were modified to demonstrate a relationship between choice of solvent and product equilibria. It was observed that benzene and toluene could shift a mixture of products and unreacted starting materials to form predominantly one imine product for a number of systems. Once the macrocyclic products had been characterized in selected solvents, iodinated halogen bonding guest molecules were added to direct macrocycle assemblies using non-covalent interactions. Studies to investigate host – guest suitability and halogen bond interactions were conducted, and it was found that tetraiodoethylene had an influence on the formation of a phenanthroline based macrocycle. Proof of concept experiments were performed to show the influence of the guest molecule, tetraiodoethylene, on the macrocyclic products formed under competitive dynamic combinatorial chemistry conditions.

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来源期刊
CiteScore
3.30
自引率
8.70%
发文量
0
审稿时长
3-8 weeks
期刊介绍: The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
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