Photophysics of novel coumarin-labeled depsipeptides in solution: sensing interactions with SDS micelle via TICT model

N-Acylbenzotriazoles enable the synthesis (69–92 % yield) of blue to green fluorescent coumarin-labeled depsidipeptides 8a–f (quantum yields 0.004–0.97) and depsitripeptides 12a–d (quantum yields 0.02–0.96). Detailed photophysical studies of fluorescent coumarin-labeled depsipeptides 8a–f and 12a–d are reported for both polar protic and polar aprotic solvents. 7-Methoxy and 7-diethylaminocoumarin-3-ylcarbonyl depsipeptides 8c,f and 12d are highly solvent sensitive. These highly fluorescent compounds could be useful for peptide assays. Further photophysical studies of 7-diethylaminocoumarin-labeled depsipeptides 8c,12d within the micellar microenvironment of SDS reflect their ability to bind with the biological membrane, suggesting potential applications in the fields of bio- and medicinal chemistry.