Doctoral thesis

Synthesis of a new bowl-shaped polyarene aiming


Thèse de doctorat: Université de Fribourg, 2014

English Efficient hydrogen storage is one of the major hurdles towards a potential hydrogen economy. Curved molecules are very interesting for this purpose because of their permanent electrical dipole moment, which can induce a dipole moment on H2 molecules increasing therefore the dipole-dipole interaction and so their adsorption. This work presents the synthesis of a new bowl-shaped polyarene based on curved corannulene’s motive. Since corannulene is known for its ability to adsorb hydrogen, the greater surface and curvature of our target molecule is assumed to increase the hydrogen adsorption. The plan was to start from phenanthrene-9,10-dione and 1-phenylpropan-2-one to obtain a planar polycyclic aromatic hydrocarbon (PAH) containing a five-membered ring. Then, via a crosscoupling reaction and a classical Scholl reaction under Kovacic conditions, it would have been possible to obtain the bowl-shaped molecule. Unfortunately, the synthesis of the first precursor presented obstacles and, from three proposed strategies, only one allowed the obtainment of the planar PAH in acceptable yield. Moreover, only one attempt for the coupling reaction was made and, because of the small amount and the impurity of the obtained product, no Scholl reaction was performed. Therefore, the desired bowl-shaped polyaromatic compound has not been obtained and the efficacy of the Scholl reaction for this synthesis has not been tested.
Faculté des sciences
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