Lipophilic nucleosides: studies toward self-assembled functional materials

Gramigna, Lucia (2014) Lipophilic nucleosides: studies toward self-assembled functional materials, [Dissertation thesis], Alma Mater Studiorum Università di Bologna. Dottorato di ricerca in Chimica, 26 Ciclo. DOI 10.6092/unibo/amsdottorato/6397.
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Molecular self-assembly takes advantage of supramolecular non-covalent interactions (ionic, hydrophobic, van der Waals, hydrogen and coordination bonds) for the construction of organized and tunable systems. In this field, lipophilic guanosines can represent powerful building blocks thanks to their aggregation proprieties in organic solvents, which can be controlled by addition or removal of cations. For example, potassium ion can template the formation of piled G-quartets structures, while in its absence ribbon-like G aggregates are generated in solution. In this thesis we explored the possibility of using guanosines as scaffolds to direct the construction of ordered and self-assembled architectures, one of the main goals of bottom-up approach in nanotechnology. In Chapter III we will describe Langmuir-Blodgett films obtained from guanosines and other lipophilic nucleosides, revealing the “special” behavior of guanine in comparison with the other nucleobases. In Chapter IV we will report the synthesis of several thiophene-functionalized guanosines and the studies towards their possible use in organic electronics: the pre-programmed organization of terthiophene residues in ribbon aggregates could allow charge conduction through π-π stacked oligothiophene functionalities. The construction and the behavior of some simple electronic nanodevices based on these organized thiopehene-guanosine hybrids has been explored.

Tipologia del documento
Tesi di dottorato
Gramigna, Lucia
Dottorato di ricerca
Scuola di dottorato
Scienze chimiche
Settore disciplinare
Settore concorsuale
Parole chiave
Supramolecular chemistry Organic electronic Guanosine
Data di discussione
14 Aprile 2014

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