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.