Synthesis, characterization and DFT study of new azaborinine compounds

Symeonidou, Evgenia (2020) Synthesis, characterization and DFT study of new azaborinine compounds. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270]
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In the framework of this thesis, a wide-ranging study of azaborinine derivatives was conducted, with a particular interest towards 9,10-B,N-phenanthrenes, holding an isosteric B-N unit in the place of a C=C bond and incorporating a B-C chiral axis. For this purpose, a preliminary theoretical study for four compounds of this class was carried out: conformational analysis and rotational energy barriers, UV-Vis absorption and fluorescence emission as well as theoretical ECD spectra of the atropisomeric structures were calculated by means of DFT and TD-DFT. An experimental attempt to synthesize and characterize another derivative of this class followed. The main synthetic concept evolved around the obtention of anti-aromatic 9-borafluorene precursors by boron-tin exchange from the reaction of a 9-stannafluorene derivative with boron reagents, followed by an aromaticity-driven ring-opening reaction of these borafluorene precursors with an organic azide. Several approaches based on similar previous works were reproduced to the closest possible version, as no absolutely inert conditions could be achieved, but the expected products were not formed; in one case, an open structure was obtained instead, for the formation of which a mechanism was proposed.

Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Symeonidou, Evgenia
Relatore della tesi
Correlatore della tesi
Corso di studio
Advanced Spectroscopy in Chemistry
Ordinamento Cds
Parole chiave
fluorescence DFT calculations conformational analysis azaborinines electronic circular dichroism
Data di discussione della Tesi
19 Ottobre 2020

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