1. Theoretical prediction of the solubility of fluorinated C(60)
- Author
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Freija De Vleeschouwer, Gregory Van Lier, Paul Geerlings, Patricia De Pril, General Chemistry, and Chemistry
- Subjects
Models, Molecular ,Fullerene ,Halogenation ,Chemistry ,Ab initio ,General Physics and Astronomy ,Fluorine ,Polarizable continuum model ,Experimental research ,Solvent ,Models, Chemical ,Solubility ,Ab initio quantum chemistry methods ,Computational chemistry ,Organic chemistry ,Polar ,Fullerenes ,Physical and Theoretical Chemistry - Abstract
Although extensive theoretical and experimental research has been conducted on fluorinated fullerenes, little detailed information exists on their solubility in different solvents. However, this solubility is crucial for their processability and possible application. In this work, we predict the solubility of fluorinated C(60) in various polar and non-polar solvents, based on a correlation between experimentally measured solubilities for C(60) from the literature and theoretically predicted solubilisation energies. These solubilisation energies are predicted using the polarizable continuum model (PCM) at the ab initio Hartree-Fock 6-31+G* level of theory. In particular, the solubilities are predicted for C(60)F(2)(n) (n = 1-10) isomers, part of the addition route to saturnene C(60)F(20). An increasing solubility is found for more polar solvents with higher degree of fluorination. With these results, we can determine the minimal fluorination degree necessary for possible solubilisation in a given solvent, and offer new perspectives to separate and purify species with different degrees of fluorination.
- Published
- 2009