Design and synthesis of new sugars- and peptides- functionalized chromophores and investigation of their supramolecular and photophysical behavior

This thesis focuses on the design and synthesis of innovative luminescent systems functionalized with sugar and/or peptide residues. These compounds present a combination of properties, merging the biocompatibility and targeting abilities of carbohydrates and peptides with the photophysical characteristics of luminescent chromophores such as porphyrins and oligophenylene ethynylenes (OPEs). • In the first chapter the design, synthesis, and characterization of new glyco-OPEs push-pull system are reported. The synthesized chromophores have shown to be characterized by strong intramolecular charge transfer, and to sensitively respond to pH change, opening the way for their and potential exploitation in cancer cells recognition • In the second chapter the design, synthesis, characterization and supramolecular behaviour investigation of dicromophoric systems based on porphyrins functionalized with glycosylated OPEs are reported. The goal has been to study how conjugation between the two chromophores could modulate their photophysical and how the sugar could influence their aggregation properties. • Finally, in the third chapter, the conjugation of di-galactose-porphyrins to bioactive peptides is reported, together with the design of peptide-porphyrin conjugated performed by Molecular Dynamics simulations. Porphyrins conjugated to peptides generally demonstrate the ability to combine diagnostic and therapeutic capabilities in a single system. Biological investigations of these systems are now ongoing. This last topic was developed at Liverpool John Moores University.