Spontaneous Resolution of the Fe(C(2)O(4))(3) Anion and Inclusion of Chiral Guest Molecules in BEDT-TTF Radical-Cation Salts.

We report the synthesis of three radical-cation salts of BEDT-TTF from racemic tris(oxalato)ferrate by electrocrystallization in the presence of chiral molecules. In the presence of enantiopure l-(+)-tartaric acid, we observe spontaneous resolution of the labile tris(oxalato)ferrate anion to produce the chiral radical-cation salt α-(BEDT-TTF)(5)[Δ-Fe(C(2)O(4))(3)].[l-(+)-tartaric acid](2) which contains only the Δ enantiomer of Fe(C(2)O(4))(3). Using enantiopure (R)-(-)-3-hydroxytetrahydrofuran as an additive gives α-(BEDT-TTF)(12)[Fe(oxalate)(3)](2).(H(2)O)(16).ethanol.(R)-(-)-3-hydroxytetrahydrofuran, which includes the chiral guest and contains a racemic mixture of Λ and Δ enantiomers of Fe(C(2)O(4))(3). Enantiopure (S)-phenyloxirane is hydrolyzed to racemic 1-phenylethane-1,2-diol to produce racemic β"-β"-(BEDT-TTF)(4)(H(2)O/H(3)O)Fe(C(2)O(4))(3).1-phenylethane-1,2-diol.