The Recognition Behaviors Between Water-soluble Pillar/Biphen Arene And Biobutylamine And The Design And The Synthesis Of Anthracene-based New Macrocyclic Compounds

In this paper,the host-guest recognition behavior and binding modes between some biological amines and water-soluble pillar[6]arene/water-soluble biphen[3]arene were studied.Meanwhile,the new anthracene-based macrocyclic host was synthesized and its host-guest recognition behavior,fluorescence behavior and color change with three model cationic guests were studied.Water-soluble pillar[6]arene and water-soluble biphen[3]arene were synthesized by introduce hydrophilic carboxylate anion to the side chain of the host and obtained the water-soluble ammonium salts by refer to the similar synthetic methods have been reported.And then the recognition behavior and binding modes of water-soluble pillar[6]arene with aromatic biogenic amines,heterocyclic biogenic amines and aliphatic biogenic amines were explored preliminary.The results of test showed that the cavity of water-soluble pillar[6]arene can completely package dopamine hydrochloride,tryptamine and spermidine hydrochloride to form stable structure.The binding constants between host and guests are all above 10⁴ M^-1,and the binding constants of dopamine hydrochloride and water-soluble pillar[6]arene is（1.47±0.60）×10⁵ M^-1.We can find that the guest structure play a key role in host-guest interaction by comparing the different bonding mode and bonding ability of host-guest recognition behavior between different structural types of biogenic amines and water-soluble pillar[6]arene.Besides,the host-guest interaction between dopamine hydrochloride,tryptamine,spermidine hydrochloride,tryptophan,arginine and water-soluble biphen[3]arene were studied.The results showed that the water-soluble bphen[3]arene can only be strongly combined by tryptamine and spermidine hydrochloride,and the binding constants between host and guests are all above 10⁴ M^-1.There are almost no interaction between dopamine hydrochloride and water-soluble biphen[3]arene.The host-guest interaction between water-soluble biphen[3]arene and amino acid such as tryptophan and arginine are small.Comparing the results of the host-guest interaction between biogenic amines and water-soluble pillar[6]arene/water-soluble biphen[3]arene,it is confirmed that the structure and cavity size of host have important influence on the bonding mode and bonding ability in the host-guest interaction.The new anthracene-based macrocyclic compound with molecular box sturcture,which formed by rigid plane structure of anthracene/benzene and flexible bridge molecular methylene ether was synthesized.The nearest distance of the new macrocyclic cavity is 3.67?,indicated there are p-p stack between anthracenes and the new macyclic has an excellent electron-rich cavity structure.Meanwhile,the new macrocyclic host has strong fluorescence properties and easy to be further modified,the new macrocylic compound has excellent physical and chemical properties.The host-guest interaction of new macrocylic compound with butylamine and trimethyl octylamine which have same octaalkyl chains showed that dibutylamine can be completely enclosed by the host cavity to form a stable structure,and trimethyl octylamine can form quasi-rotane structure with new macrocylic host compound.Fluorescence test showed that the binding constants of butylamine and trimethyl octylamine are（4.16±0.68）×10⁵ M^-11 and（1.07±0.15）×10⁵ M^-1.The host-guest interaction between new macrocylic compound and 4,4’-butyl bipyridine was studied.The test showed that the guest was completely enclosed in the cavity of host to form stable structure.The color of the mixture solution of 4,4’-butyl bipyridine and host can quickly change to visible red and the strong fluorescence quenching of host are accompanied.Fluorescence test showed that there are strong complexation and the bonding constant of 4,4’-butyl bipyridine and new macrocylic compound is（2.16±0.29）×10⁷ M^-1.The new macrocylic compound is expected to be used for bipyridine detection and separation of pesticide.