This thesis presents new strategies to improve mechanosensitive Flipper probes used to image membrane tension and order in living cells. Cellular membranes regulate essential biological functions through changes in lipid packing and curvature, which can be monitored with fluorescent probes. Although Flipper-TR set the benchmark for such measurements, its brightness and plasma membrane selectivity had not been significantly improved. In the first part, peptide dendrimers of different generations were developed as modular platforms to enhance membrane insertion and fluorescence intensity. Coupling dendrimers with specific lipid anchors enabled selective targeting of ordered or disordered membrane regions, resulting in brighter probes that allow imaging at lower excitation power and reduced phototoxicity. The second part focused on tuning the electronic donor site of the mechanophore using acetal and thioacetal groups, improving chemical stability and modulating electronic response through chalcogen-bonding interactions. Together, dendrimer-assisted delivery and donor optimization produced brighter, more stable, and more sensitive probes that outperform Flipper-TR for quantitative membrane mechanics imaging.