Synthesis of nucleobase-calixarenes via click chemistry and evaluation of their complexation with alkali metal ions and molecular assembly
In this study, calixarene derivatives (11–14) bearing a single nucleobase (adenine, thymine, cytosine or guanine) were synthesised via click chemistry. The complexation ability of the synthesised derivatives with alkali metal ions was measured using MALDI-TOF mass spectrometry, and their molecular assembly in CDCl3 was determined using 1H NMR. Calixarene derivatives (11–14) formed 1:1 complexes with all alkali metal ions and the rank order for the complexation selectivity was Rb+ > Cs+ > K+ ≅ Na+ > Li+. The attachment of nucleobase at the upper rim of calixarene had little effect on its complexation selectivity for alkali metal ions. Thymine-, adenine- and guanine-calixarenes formed self-assembled structures in CDCl3 via base–base interactions. In addition, adenine-calixarene (11) bound to thymine-calixarene (12) to form a discrete species via Hoogsteen hydrogen bonding.
Minier, M. A.,
Franz, A. H.,
Synthesis of nucleobase-calixarenes via click chemistry and evaluation of their complexation with alkali metal ions and molecular assembly.
Supramolecular Chemistry, 23(12), 806–818.