Electroactive bio-based chiral tweezers: Attractive selectors for enantioselective voltammetry

Control of Molecular Packing in Crystal and Electron Communication of Two Ferrocenyl Moieties across Chiral Isomannide or Isosorbide Bridge

“…These functional groups can be easily derivatized, to obtaining a plethora of derivatives whose properties depend both from the characteristics of the introduced functional groups and from the different stereochemical arrangement of the hydroxyl groups [23,[26][27][28][29]. In previous studies [30][31][32][33][34][35], some of us successfully employed these compounds as starting materials for the synthesis of new chiral auxiliaries [30][31][32][33] and light-emitting materials [34]. These studies highlighted the importance of the chiral backbone, which leads to an interaction between the functional groups linked to the central scaffold, with a great influence on the final properties, both in isomannide 1 and isosorbide 2.…”

“…These studies highlighted the importance of the chiral backbone, which leads to an interaction between the functional groups linked to the central scaffold, with a great influence on the final properties, both in isomannide 1 and isosorbide 2. Moreover, some peculiar derivatives showed interesting applications in electrochemistry-related studies [31].…”

“…In previous studies [30][31][32][33][34][35], some of us successfully employed these compounds as starting materials for the synthesis of new chiral auxiliaries [30][31][32][33] and light-emitting materials [34]. These studies highlighted the importance of the chiral backbone, which leads to an interaction between the functional groups linked to the central scaffold, with a great influence on the final properties, both in isomannide 1 and isosorbide 2.…”

“…We focused our attention on derivatives 3 and 4 due to their ease of preparation, by simple double esterification of the free hydroxy groups, and to gain a deeper insight into the different dispositions of the two ferrocene moieties around the central chiral scaffold, an interesting feature to have a deeper insight in the influence of stereochemistry on electron communication. Compounds 3 and 4 were synthesized following the known protocols developed for the preparation of other isohexide diesters [30,31,36]. These new derivatives, obtained as crystalline solids, were fully characterized through X-ray diffraction analysis (XRD) to gain more insight into their properties in the solid state.…”