Self-sorting chiral organogels from a long chain carbamate of 1-benzyl-pyrrolidine-3,4-diol

(3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(dodecylcarbamate), a pyrrolidine ring bearing two long carbon chains connected by carbamate functionalities, gave origin to stable gels both in polar and apolar solvents. Several experimental and theoretical techniques (Cryo-TEM, AFM, DSC, circular dichroism (CD), molecular mechanics calculations and CD simulations) were used to describe the formation and the characteristics of chiral supramolecular structures and fibers constituting the gel. The chirality both at supramolecular and microscopic level depends on the configuration of the stereogenic centers of the pyrrolidine unit. The gels formed by the two enantiomers of the gelator and their mixtures display enantiomeric discrimination resulting in a self-sorting process. In fact, separate fibers of opposite helicity are obtained which suggest strong potentialities of this class of compounds for the realization of functionalized chiral architectures