Perfluorinated polycyclic aromatic hydrocarbons: anthracene, phenanthrene, pyrene, tetracene, chrysene, and triphenylene

The Journal of Physical Chemistry. a
Xue-jun FengHenry F Schaefer

Abstract

The properties of perfluoroanthracene (1-C(14)F(10)), perfluorophenanthrene (2-C(14)F(10)), perfluoropyrene (C(16)F(10)), perfluorotetracene (1-C(18)F(12)), perfluorochrysene (2-C(18)F(12)), and perfluorotriphenylene (3-C(18)F(12)) and their radical anions have been studied using density functional theory (DFT). Three measures of neutral-anion energy separations reported in this work are the adiabatic electron affinity (EA(ad)), the vertical electron affinity (EA(vert)), and the vertical detachment energy (VDE). The vibrational frequencies of these perfluoro PAHs and their radical anions are also examined. The predicted adiabatic electron affinities (DZP++ B3LYP) are: 1.84 eV, 1-C(14)F(10); 1.41 eV, 2-C(14)F(10); 1.72 eV, C(16)F(10); 2.39 eV, 1-C(18)F(12); 1.83 eV (C(i) symmetry) and 1.88 eV (C(2) symmetry), 2-C(18)F(12); and 1.69 eV, 3-C(18)F(12). The perfluorotetracene is clearly the most effective electron captor. Perfluorophenanthrene, perfluoropyrene, perfluorochrysene, and perfluorotriphenylene, as well as their radical anions deviate from planarity. For example, the nonplanar perfluorochrysene structures are predicted to lie 7-13 kcal/mol below the pertinent C(2h) stationary points.

References

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Jul 20, 2006·Journal of the American Chemical Society·Damian MoranHenry F Schaefer

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Citations

Dec 14, 2016·The Journal of Physical Chemistry Letters·Begoña Milián-Medina, Johannes Gierschner
Aug 6, 2019·Chemistry : a European Journal·Karlee P CastroOlga V Boltalina
May 29, 2009·The Journal of Physical Chemistry. a·Judy I WuJosé Elguero
Sep 14, 2010·Journal of Chemical Theory and Computation·Frank Jensen
Sep 22, 2012·The Journal of Physical Chemistry. a·Mikko KaipioDage Sundholm

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