The Synthesis Of Novel Supramolecular Host Based On Naphthalene And Their Host-Guest Properties

In 1978,C.J.Pedersen,J.M.Lehn and D.J.Cram won the Nobel prize in chemistry to commend their pioneering work in the theory and initiative practice in supramolecular chemistry.Since then,supramolecular chemistry has been developing rapidly as a new frontier science,and has attracted more and more attention from scientists.It has penetrated into every field of chemistry and even science,and has played an invaluable role.Therefore,for the supramolecular chemical researchers,it is a great significance to synthesize a new and efficient supermolecular macrocycles.In recent years,few studies have been done on the supramolecular macrocycles with naphthalene as backbone,but naphthalene ring has more electron cloud and larger surface area than benzene ring.Therefore,if the structural design is suitable,a new functionalized supermolecular macrocycle can be synthesized.And then use its excellent host and guest body selectivity,and use it in biomedicine,artificial simulation,drug delivery and so on to benefit mankind.The specific research contents of this paper are as follows:(1)The development history of supramolecular chemistry and several classical supramolecular macrocycles are briefly introduced.The progress of self-assembly and molecular recognition which based on π-π stacking,hydrogen bond,and hydrophobic interaction in supramolecular chemistry in recent years are also discussed.(2)These oligomers of naphthalene as backbone were synthesized.Their molecular structures were determined by MS,NMR and single crystal X-ray diffraction.Meanwhile,their specific host-guest properties were studied by 1H-NMR titration.(3)A molecule with two hydrogen bond accepter inside the cavity and two hydrophilic carboxyl groups in the tail of the macrocycle was synthesized.Its molecular structure was confirmed by MS,NMR,crystal X-ray diffraction.UV fluorescence titration,ITC titration were used to explore the host-guest properties with different acetal compounds,focus on how the intermolecular hydrogen bond and hydrophobic interaction influence bonding constant,which attempts to explain the laws of dynamic thermodynamics in physical organic chemistry.