A Single Methyl, Cyclohexyl Substituted Cucurbituril Synthesis, Characterization, And Nature Study

Along with the development of supramolecular chemistry,Cucurbit[n]uril(Q[n]) as a new type with a specific point-like cavity of supramolecular compounds, with the super-special properties of molecules was found. Later States scientists have reported on different types of modified Cucurbit[n]uril(Q[n]) and Central Properties.Its molecular recognition and self-assem blyofcatalytic function, etc. is a major development.However, Cucurbit [n]uril(Q[n]) ring in the water, organic solvents poor solubility, This largely restricted Cucurbit[n]uril(Q[n]) Central further study and application. Therefore, improving the solubility of Cucurbit[n]uril(Q[n]) in Central study become part of an important research topic.Recently, a number of fully and partially substituted Q[n] have been reported. These include the fully substituted (cyclohexano,CyH) (CyH)₂Q[5] and (CyH)₂Q[6], Me₁₂Q[6] and (HO)_2nQ[n] and the partially substituted Ph₂Q[6],Me₆Q[6],Me₄Q[6] and (Me₂CyP)_nQ[6]. In addition there has been one report of substituted cucurbituril analogues. While achieving organic solubility, the fully substituted Q[n], suffer the limitation that Q[5] is always the major product and that overall yields are lower. Partial substitution, on the other hand, avoids these problems and also precludes the need to use large quantities of potentially difficult to obtain or expensive substituted glycolurils. We successfully achieved the dicyclohexanocucurbit[6]uril, (CyH)₂Q[6] by condensing the diether of cyclohexanoglycoluril with the glycoluril dimer produces a new symmetrical substituted Q[n], dicyclohexanocucurbit[6]uril, (CyH)₂Q[6] (scheme 1) in a controlled manner.the (CyH)₂Q[6] shows good water solubility, which allowed us to investigate the structure and the host guest binding properties of this new substituted Q[n].In this work, Paraformaldehyde, methl-glyoxoal, urea and cyclohexanone as raw materials, Synthesis cyclohexyl substituted glycoluril ether and single-methyl substituted glucoluril. And then, use the two kinds of substituted glycoluril in hydrochloric acid-catalyzed to synthesize the single-methyl and cyclohexyl substituted of cucurbit[n]uril. At the same time, use TLC plate tracked and identificated the process of this reaction. With acetone and 1,4-dioxane separated the crude product of cucurbituril(Q[5]) and cucurbituril(Q[6]). Crude product was separated through fractional crystallization, recrystal, column chromatography and add guest to the complex solution, and the crystal of single-methyl and cyclohexyl substituted of cucurbit[6]uril has been achieved, the crystal was analyzed by single crystal X-ray diffraction. This new members of the cucurbituril family should be useful for development of a wide range of cucurbituril functional materials. Meanwhile, the interaction of (CyH)₂Q[6] and (CyH)₆Q[6] with some guest molecular and CuSO4 have been studied in this paper, and prepared there crystals, these crystals were analyzed by single crystal X-ray diffraction. Their crystal structures characterized by single-crystal X-ray diffractions revealed that these hosts can form supramolecular assemblies through the ion-dipole interaction, hydrogen binding, C-H…p or N-H…p interaction and p…p tacking. 44bpy, m4 and p6 were interacted with (CyH)₂Q[6] formed a supramolecular chain, 55mbpy, 4phimdl were interacted with (CyH)₂Q[6] formed many supramolecular holes, 2pimdl was interacted with(CyH)₆Q[6] formed supramolecular assemblies though back to back closed packing. (CyH)₂Q[6] and CuSO₄ were formed supramolecular chains through hydrogen-bonding.