| Title |
Ertminės ir polimerinės nanovamzdelinės savitvarkės sistemos, susiformavusios dėl vandenilinių ryšių tarp mažų biciklinių monomerų / |
| Translation of Title |
Hydrogen bonded cavity and polymeric nanotubular assemblies from small bicyclic monomers. |
| Authors |
Račkauskaitė, Dovilė |
| Full Text |
|
| Pages |
30 |
| Keywords [eng] |
hydrogen bonds ; self-assembly ; 9-azabicyclo[3.3.1]nonane ; tautoleptic aggregation ; isocytosine |
| Abstract [eng] |
In this work strategies that allow control of supramolecular outcome of monomers containing bicyclic framework fused with isocytosine and/or ureidopyrimidinone motifs are discussed. The control over aggregation is attained by changing the size of the side chains and by attaching carbamide substituents at the isocytosine motif. Formation of a complex H-bonded decameric capsule assembled from bis-isocytosine monomers in CS2 is presented. The assembly is driven by solvent induced tautomerisation of the isocytosine motif, i.e. heteroleptic aggregation, and simultaneous establishment of 3H- and 2H-bonding modes. The large cavity of the capsule was utilized for C60 inclusion. Enantiomer resolution of 9-benzyl-9-azabicyclo[3.3.1]nonane-2,6-diol was performed. This precursor was utilized in the synthesis of bis-isocytosine monomers, which assemble into polymeric nanotubes. The tubular assemblies are held by orthogonal inter-tetramer H-bonding interface, established after tautoleptic aggregation into tetrameric rings. Bis-ureidopyrimidinone monomers were synthesized and their aggregation in solution investigated. Short organic nanotube composed of eight identical monomers that incorporates isocytosine and ureidopyrimidinone motifs was designed. After isocytosine-ureidopyrimidinone hetero-association via 3H-bonding new inter-tetramer H-bonding interface is created. The octameric tube undergoes extreme structural switch into cyclic tetramer upon inclusion of C60 and C70 guests. |
| Dissertation Institution |
Vilniaus universitetas. |
| Type |
Summaries of doctoral thesis |
| Language |
Lithuanian |
| Publication date |
2016 |
