Synthesis And Application Of The Isolating Material Of Supramolecular System Contains Diyne Structure

Supramolecular Chemistry was a new field which emerged only decades ago. It isreported that, Compounds contain the diyne-diol structure, for example,1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol (D.D, abbr.), have an excellent property ofrecognizing guest molecular such as alcohols, phenols, amines and lactones by formingcrystalline complexes with them via hydrogen bond, van der waals force and π-π stackinginteractions, by which separation and purification was accomplished. This method performedwell on applying to recognize and separate the effect component of Chinese drug. Comparedto traditional method, supramolecular system has a variety of advances such as highselectivity, high purity and convenient workup and recyclable on recognizing, separating andincluding one or two specific component in a mixture, which will be competetive inapplication. Hence, it is important to study the synthesis route of compounds contain thediyne-diol structure.In this thesis, we designed and synthesized three compounds contain the diyne-diolstructure. After that we explored their inclusion property. The main results are as follows:2-butayne-1,4-diol (compoundⅠ), thionyl chloride and pyridine were utilized as rawmaterials to synthesize1,4-dichloro-2-butayne (compoundⅡ), conditions of the reaction wereoptimized.1,3-budiyne (compound Ⅲ) was obtained by eliminating1,4-dichloro-2-butayne(compoundⅡ) with alkaline, conditions of the reaction were optimized.1,3-budiyne-1,4-diyl-bis(bromomagnesium)(compoundⅣ) was obtained.1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol (compound Ⅴ),1,1’-(buta-1,3-diyne-1,4-diyl)dicyclopentanol (compound Ⅶ) and1,1’-(buta-1,3-diyne-1,4-diyl)dicyclohexanol (compoundⅧ) was obtained by reacting compound Ⅳ with benzophenone, cyclopentanone andcyclohexanone. Structures of the intermediate and target compounds were characterized by IR,1HNMR, MS and HRMS.The inclusion property of the synthesized compounds contain the diyne-diol structurewas experimented. Complexes were characterized by IR and1HNMR. Host-Guest ratios wereconformed.The inclusion propriety of D.D was applied on two Chinese drugs. The complexes werecharacterized by IR,1HNMR and XRD. Host-Guest ratio was conformed.