Synthesis And Supramolecular Chemistry Of Naphthotubes With Imidazole Or Amide Linkers

Molecular recognition is the basis of numerous biological phenomena and supramolecular chemistry.In the past few decades,a great of achievements have been made on molecular recognition.Many synthetic receptors with unique recognition properties have been reported.This not only helps us understand molecular recognition but also these synthetic receptors are already widely used in sensing,assembly and catalysis.However,we still need to develop more synthetic receptors to solve the problems such as water pollution,air pollution,recycling of chemical raw materials in our daily life.In this paper,two new supramolecules,naphthotubes with imidazole or amide linkers,were synthesized and their applications were studied.There are totally three parts in this paper.The first chapter is the introduction,which mainly introduces the research progress of supramolecules which can identify aromatic rings in recent years,and the second and third chapters are the main research contents.1.Synthesis and application of naphthotubes with imidazole linkerIn this chapter,naphthotubes of two pairs of imidazolium cations with anions of BAr F?and PF6? and their solvent effects in combination with aromatic guest such as naphthalene,anthracene,phenanthrene and anthracene are studied.The formation of naphthotubes was determined by NMR and Mass Spectrometry.2D NMR determined the chemical shift values of the numbered proton peaks of the naphthotubes.The single crystal determines the absolute configuration of the naphthotubes.The bonding constant of hosts and guests are determined by H NMR in different polarities solvents such as CD2Cl2,CD3 CN,DMSO-d6,and their mixture.The results show an anomaly: the bonding constant is greater in solvents with higher polarity,which is the result of solvent effects and ion pair dissociation effects.The DFT calculation results show that there are cation ????,C-H????,????? interactions between the host and the guest,and the bond ratio of the host and guest is 1:1 which determined by the Job's plot and the molar ratio plot.2.Separation benzene from the mixture by amide-bridged naphthotubesBenzene,cyclohexene and cyclohexane are all important chemical raw materials and have less polar,which are difficult to separate by near-boiling distillation technology.In this paper,we synthesized a pair of naphthotubes which have methoxy groups in their side and studied their adsorption properties for benzene,cyclohexene and cyclohexane.We have found that both cis-and trans-naphthotubes rapidly and selectively adsorb benzene,the capablity of trans-naphthotube is more stand out.The two naphthotubes have little BET,the crystal structure indicates that benzene is inside the naphthotubes and is bound in a 1:1,and the adsorption molar ratio of the naphthotubes with benzene more than 1:1.Compared to other adsorbent materials such as MOFs and COFs,naphthotubes have more chemically stable and can be recycled.Although the adsorption amount of benzene in the naphthalene modified molecular tube is not high,the adsorption rate is fast and high purity benzene can be obtained by one adsorption.In the future,we will further develop the practical application of naphthotubes with different structures as gas adsorbing materials and water purifying materials.