Synthesis, Characterization and Conformational Studies of Modified Carbazole-bis-aryl-boranes

Foschi, Simone (2020) Synthesis, Characterization and Conformational Studies of Modified Carbazole-bis-aryl-boranes. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270]
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During this project we have synthetized different compounds belonging to the class of amino-boranes for the study of bis-aryl-B=N system. We have decided to keep unchanged the aryl components and change only the amine to observe the effect of that on the B=N bond. The used amines are modified carbazoles with functional groups chosen to amplify or disempower the steric and the conjugation effect. We have found that the evaluation of steric barrier was possible studying the gearing aryls rotation around the C-B bonds, while the conjugation barrier is instead given by the energy needed to break the formal double bond B=N and allow the amine rotation. The work started with a proposed synthesis, improved for every reaction, then the products are characterized by NMR, fluorometric spectroscopy, mass spectrometry and X-Ray diffraction on single crystal. The following study on rotational energy barrier was possible theoretically through DFT calculation and experimentally with techniques like Dynamic NMR and EXSY. The fluorometric analysis was done for the study of the solvatochromic propriety of the products.

Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Foschi, Simone
Relatore della tesi
Correlatore della tesi
Corso di studio
Ordinamento Cds
Parole chiave
amino-boranes DFT Bis-Arylboryl-amine carbazole DNMR fluorescense modified-carbazoles EXSY propellers
Data di discussione della Tesi
26 Marzo 2020

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