Inclusion of organic cations by calix[4]resorcinarenes modified with sulfonic acid groups
Calix[4]resorcinarene,as an important branch of the third generation supramolecular compounds,calixarene,have received increasing attention for their functionalized modifications in recent years.In this paper,calix[4]resorcinarenes were synthesized by using resorcinol as the starting material,and calix[4]resorcinarene sulfonic acid derivatives 2a and 2b were synthesized by introducing sulfonic acid groups at their C-2 positions with methylene as a bridge link.The inclusion behavior of 2a and 2b towards solvent molecules and organic ammonium salts was studied.The molecular structures of 2a·Me4NCl and 2b·MeOH were determined by X-ray single-crystal diffraction,indicating their 1∶1 inclusion formation.Of which,the ammonium cations were encapsulated by dimer of 2a in 2a·Me4NCl.The 1H NMR characterization was performed to investigate the inclusion of 2b with Et4NCl and n-Bu4NCl,the results showed that the N+head of ammonium salts are embedded to sulfonic acid groups of 2b.Ultraviolet(UV)spectrum was performed on studying the relationship of absorption of inclusion complex and concentration ratio of host and guest.Moreover,the catalytic effect of 2a·Me4NCl in the synthesis of triglycidyl isocyanurate was examined,and it was found to possess good catalytic properties.
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