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Taming Hot CF3 Radicals: Incrementally Tuned Families of Polyarene Electron Acceptors for Air-Stable Molecular Optoelectronics

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  • We thank the U.S. NSF (CHE-1012468 (SHS/OVB) and the Colorado State University Research Foundation for generous support. The PES work was supported by the U.S. Department of Energy (DOE), Division of Chemical Sciences, Geosciences and Biosciences, Office of Basic Energy Sciences and was performed at the EMSL, a national scientific user facility sponsored by DOE’s Office of Biological and Environmental Research and located at Pacific Northwest National Laboratory, which is operated for DOE by Battelle.

Abstract

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A regioselective, solvent-, and catalyst-free method for the perfluoroalkylation of polycyclic aromatic hydrocarbons (PAHs) with CF3I was used to synthesize air-stable organic electron acceptors (PAH(CF3)n). The gas-phase electron affinities of these compounds correlate to the number of CF3 groups. The number and orientation of the CF3 groups also influenced the π–π stacking and crystalline morphologies of these compounds.

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