Strategies toward phosphorus-containing PAHs and the effect of P-substitution on the electronic properties

Rózsa Szűcs (1, 2) , François Riobé (1) , Aude Escande (1) , Damien Joly (1) , Pierre-Antoine Bouit (1) , László Nyulászi (2) , Muriel Hissler (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 BME - Budapest University of Technology and Economics [Budapest]

In this paper, we report on the different synthetic strategies which led to the preparation of a whole family of polyaromatic hydrocarbons containing a P-atom at the edge. In particular, we show from both experimental and theoretical perspective how the Scholl method has to be adapted to the specificity of organophosphorus derivatives. The P-modified PAHs possess the classical phosphane reactivity that allows fine-tuning of their electronic properties as evidenced by spectro-electrochemistry and theoretical calculations. In particular, the effect of P-substitution on the aromaticity of the different cycles of the PAH was studied.

Keywords: Spectro-electrochemistry; Organophosphorus chemistry; Polyaromatics; Aromaticity

Domains: Chemical Sciences; Organic chemistry

Rózsa Szűcs, François Riobé, Aude Escande, Damien Joly, Pierre-Antoine Bouit, et al.. Strategies toward phosphorus-containing PAHs and the effect of P-substitution on the electronic properties. Pure and Applied Chemistry, 2017, 88 (3), pp.341-356. ⟨10.1515/pac-2016-0909⟩. ⟨hal-01450088⟩