Eventually, three molecules, 8, 11 and 13, were selected to be synthesized as suitable ORA candidates, namely: Symmetrical DIPA, bearing prop-2-yn-1-ol moieties in positions 9 and 10 is expected to release O2 at low temperature and to be more suitable for further functionalization and increased water solubility thanks to the terminal hydroxyl groups. Unsymmetrical PCPA and PFPA, bearing a prop-2-yn-1-ol moiety in position 9 and a para benzoic acid or a para fluorophenyl group, respectively, in position 10, were supposed to generate EPOs more stable than DIPA, but more labile than PABA. The different ionisable and non ionisable appendages may be an interesting feature to regulate their solubility and further covalent or non-covalent manipulation.