Supramolecular Self-assembly Based On Calixarene And Binaphthyl Diphenol

Chiral functional materials are an important research topic of material chemistry,because many key processes in organisms are affected by specific chiral substances.Supermolecular chirality,which can be obtained by self-assembly of chiral or achiral molecules,is an important part of chiral researchs.Sulfonatocalixarenes are widely used in molecular recognition and assembly due to unique structural advantages.Sulfonatocalixarenes show strong bonding abilities towards guests such as organic cations due to the electron-rich cavities and the hydrophilic sulfonic acid groups at the upper edge.In the supramolecular assemblies,small organic cations can be encapsulated in the hydrophobic cavity and the hydrophilic groups(sulfonic acid groups in the upper edges and phenolic hydroxyl groups in the lower edges)can participate in the amphiphilic assembly process to form nano supramolecular assemblies.Binaphthols endow a C2 symmetry axis,which are widely used in chiral recognitions,asymmetric catalytic,chiral auxiliary,chiral resolving reagents.The phenolic hydroxyl groups can be easily derivatized with no change in the chirality.In recent years,synthesis of new chiral molecules based on chiral binaphthols is becoming more hotter research field.Therefore,binaphthols have also been used in the field of supramolecular assembly to introduce chirality to supramolecular assemblies.Therefore,we designed a series of binaphthols derivates with the biding sites of organic cations.The series of derivates can be easily obtained through the reaction between the binaphthol skeletons with the common reactants such as 4-pyridinylboronic acid,4-vinyl pyridine and 4-formylphenylboronic acid.The modified sites have strong binding abilities with the macrocyclic hosts such as sulfonatocalixarenes and cucurbiturils.The axial chirality of binaphthanol molecules is introduced into supramolecular assemblies by host-guest interactions.Their optical properties were studied by ultraviolet spectrophotometer,fluorescence spectrophotometer,circular chromatograph with so on.Based on the research,the relationship between molecular structures and supramolecular chirality,clarify influence of assembly mode on the supramolecular chiralitymay be revealed.