Mechanically Interlocked Profragrances for the Controlled Release of Scents

The synthesis of a series of interlocked profragrances and the study of the controlled release of the corresponding scents are reported. The structures of the profragrances are based on a [2]pseudorotaxane scaffold with a fumaramate thread derived from perfumery alcohols and a tetrabenzylamido ring. The delivery of the scents was accomplished by sequential thermal dethreading and further enzymatic hydrolysis. Alternatively, the dethreading can be achieved by increasing the polarity of the solvent or photochemical isomerization. The temperature of dethreading can be modulated by the steric demand of the ends of the thread, which allows the selection of different precursor structures depending on the desired rates of delivery. The inputs and outputs for the controlled release of the interlocked profragrances correspond to those of YES or AND logic gates.

Automated summary

A series of interlocked profragrances were synthesized based on a [2]pseudorotaxane scaffold, with controlled release achieved through thermal dethreading, enzymatic hydrolysis, increasing solvent polarity, or photochemical isomerization. The steric demand of the thread's ends modulates the temperature of dethreading, allowing for different rates of delivery depending on precursor structures. The controlled release of the interlocked profragrances corresponds to inputs and outputs similar to YES or AND logic gates.