Synthesis, characterization and complexation behavior investigations of novel starburst-like tris-crown ethers

Abstract

The novel unique structures of starburst-like tris-crown ethers were successfully synthesized from 1,3,5-tri-acryloylhexahydro-1,3,5-triazine (TAHTA) with amino- and aza- crown ethers through Michael addition. The crown ethers contained primary and secondary amine groups such as 2-aminomethyl crown ethers, 4-aminobenzo crown ethers and 1-aza crown ethers. The newly synthesized starburst tris-crown ethers were characterized by elemental analysis, IR, ¹H-NMR, ¹³C-NMR and FAB mass spectroscopy, respectively. The newly synthesized host compounds of tris-crown ethers showed complexation abilities with various sizes of alkali metal cations such as Na⁺, K⁺, Rb⁺ and Cs⁺. The complexation behavior was examined by ¹H-NMR, FAB mass spectroscopy and UV spectroscopy.