Synthesis of nucleobase-calix[4]arenes via click chemistry and evaluation of their complexation with alkali metal ions and molecular assembly
Document Type
Article
Publication Title
Supramolecular Chemistry
Department
Chemistry
ISSN
1061-0278
Volume
23
Issue
12
DOI
10.1080/10610278.2011.632824
First Page
806
Last Page
818
Publication Date
11-28-2011
Abstract
In this study, calix[4]arene 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. Calix[4]arene 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 calix[4]arene had little effect on its complexation selectivity for alkali metal ions. Thymine-, adenine- and guanine-calix[4]arenes formed self-assembled structures in CDCl3 via base–base interactions. In addition, adenine-calix[4]arene (11) bound to thymine-calix[4]arene (12) to form a discrete species via Hoogsteen hydrogen bonding.
Recommended Citation
Liu, W.,
Minier, M. A.,
Franz, A. H.,
Curtis, M.,
&
Xue, L.
(2011).
Synthesis of nucleobase-calix[4]arenes via click chemistry and evaluation of their complexation with alkali metal ions and molecular assembly.
Supramolecular Chemistry, 23(12), 806–818.
DOI: 10.1080/10610278.2011.632824
https://scholarlycommons.pacific.edu/cop-facarticles/136
