New Macrocycle Synthesis, Part VIII [1]. The Synthesis of Dibenzo(3 k +2(crown- k And Cationic Recognition With Fluorescence Spectroscopy

Abstract

Macrocycles of dibenzo(3 k +2(crown- k , ( k =6-9) were synthesised from the condensation of bis(3-hydroxyphenoxy)glycols with polyglycol dihalides or ditosylates in the presence of alkali carbonates/DMSO. Bis(3-hydroxyphenoxy) ended glycols were obtained from resorcinol and dihalides of mono or diethylene glycols in water/NaOH in good yields. The products were identified with IR, high-resolution EI and FAB mass spectrometry, 1 H and 13 C-NMR spectroscopy. The binding properties of macrocycles with K + , Na + and Li + were investigated with the steady state fluorescence spectroscopy in acetonitrile at room temperature. Macrocycles exhibited complexation enhanced quenching with alkali perchlorates while showing complexation enhanced fluorescence spectra with alkali thiocyanates to give association constants. They mostly displayed better Na + binding selectivity compared to those of K + and Li + ions.