Synthesis Of Bis-naphthalene Moleculars And Construction Of Supramolecular Polymers

The?-?stacking interactions between the electron-rich aromatic planes are widely used to construct supramolecular polymers.However,the stacking of electron-rich aromatic planes is not very ideal,since the repulsion between their surfaces can lead to disordered and non-directional stacking.The rigid curved skeleton which has a fixed configuration and natural bending,can avoid these problems,and has unique advantages in the construction of rigid artificial molecular clamp receptor and supramolecular polymer systems.In this paper,1-naphthol,2-naphthol were used as raw materials to react with tetramethoxypropane and aldehyde,respectively.Then five bis-naphthalene/bis-anthracene moleculars with different bridges and substituents were obtained.And binding constants of several bis-naphthalene/bis-anthracene moleculars with the electron-deficient guest 8D8²⁺was determined by ¹H-NMR.It was found that the molecular structure and properties of the molecular tweezers could be changed by changing the bridge,two arms or substituents.Finally,the interaction with guests was affected.And the perfect V-shaped cleft is favorable for the complexation with the electron-deficient guest.In this paper,water-soluble sodium sulfonate and quaternary ammonium salt were synthesized by attaching the charged water-soluble groups SO₄^2-and NH₄⁺to the curved skeleton of bis-naphthalene.They can self-assemble under CH-?interaction and hydrophobicity,forming disc-like two-dimensional supramolecular polymers in aqueous media.At the same time,two kinds of isocyanates were synthesized from methyl trihydroxybenzoate,and they were coupled with bridged dinaphthylamine to give two compounds with bis-urea groups.It has been found by experiments that one of the compounds can form a gel in nonpolar solvents such as aliphatic hydrocarbons and aromatic hydrocarbons.And the gel of the compound in petrol,kerosene,diesel oil and engine oil were also obtained.The rheological properties of the gel in petrol was tested and found to be mechanically strong enough to be successfully used in the laboratory for the recovery of gasoline from water and seawater.The recovery of petrol is environmentally friendly and the gel factor can be recycled,which means the organogelator has certain application prospects.