Polymerizable Atropisomeric Bis-arylboryl-Carbazoles: Synthesis and Characterization

This thesis focuses on the synthesis and characterization of bis-arylboryl-carbazoles, whose structure has a B-N bond with double bond character that affects their main fluorescence properties. The boron atom of the molecule is bound to the nitrogen of a carbazole functionalized at position 2 with a methacrylic group and two different aryl groups: a mesityl and a 1-methyl-3-(trifluoromethyl)benzene. In parallel, a conformational study was conducted through DFT and TD-DFT method to identify the ground states and transition states of the molecule, extrapolate ECD spectra, and evaluate geometries and energies involved during luminescence phenomena. Given the presence of stereogenic axes, the diastereoisomers of the molecule were separated by CSP-HPLC. Absolute configurations were identified through ECD, NMR and NOE, and kinetics studies were conducted to evaluate the experimental rotational barriers through Dynamic NMR and Dynamic HPLC. Finally, the molecule was incorporated into a polymer structure and analyzed by solid-state fluorescence spectroscopy.