2026-09-25T15:05:21Z https://epublications.vu.lt/oai

oai:vu.lt:elaba:16990407 2026-07-08T00:44:29Z openaireNDLTDDRIVERDART-EUROPE

Hydrogen bonded cavity and polymeric nanotubular assemblies from small bicyclic monomers /Ertminės ir polimerinės nanovamzdelinės savitvarkės sistemos, susiformavusios dėl vandenilinių ryšių tarp mažų biciklinių monomerų.Anderson, Dovilė,info:eu-repo/semantics/openAccesstubular polymers ; hydrogen bonding ; self-assembled capsule ; tautoleptic aggregationIn 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.Institutional Repository of Vilnius UniversityButkus, EugenijusOrentas, Edvinasinfo:eu-repo/semantics/doctoralThesiseng2016application/pdfhttps://epublications.vu.lt/object/elaba:16990407/16990407.pdfhttps://repository.vu.lt/VU:ELABAETD16990407&prefLang=en_US