Design of new organic acceptor molecules with the larger π systems are of interest because they typically demonstrate better charge transport properties and smaller HOMO-LUMO gaps. For example, acenes and phenacenes represent such families, in which members with five fused aromatic rings exhibit some of the highest measured mobilities in the thin-film field effect transistors. Cyclization in halogenated polycyclic aromatic hydrocarbons (PAHs) is well studied, and typically involves chlorinated, brominated, and more recently, fluorinated derivatives. Reported here is the study of expansion of the selected polyaromatic systems and their fluorinated derivatives via literature syntheses and original methods. An array of spectroscopic methods was used for structural and physicochemical properties characterization. Results were highly reproducible, and good yield and selectivity were observed in some cases. 1. Makosza, M., Winiarski, J.: Vicarious Nucleophilic Substitution of Hydrogen. Acc.Chem.Res. 1987, 20, 282-289. 2.Makosza, M.: Synthesis of heterocyclic compounds via Vicarious nucleophilic substitution of hydrogen. Pure Appl. Chem. 1997, 69, 559-564. 3.Allemann, O., Duttwyler, S., Romanato, P., Baldridge, K. K., Siegel, J. S.: Proton-Catalyzed, Silane-Fueled Friedel-Crafts Coupling of Fluoroarenes. Science 2012, 332, 574-577. 5.Hughes, R. P.; Lindner, D. C.; Rheingold, A. L.; Yap, G. P. A.: Perfluorobenzyl complexes of cobalt and rhodium. Unusual coupling between pentafluorophenyl and pentamethylcyclopentadienyl rings. Organometallics 1996, 15, 5678-5686.

Expansion of polyaromatic π systems via fluoroannulation reactions

249th National Meeting (2015)

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