Aggregation-induced emitting (AIE)
luminophores are sensitive and
easy-to-handle types of probes that allow driving a stimulus-responsive
off/on optical tool through the manipulation of the aggregation behavior.
In this work, tetraphenylethene (TPE)-phenylalanine derivatives, characterized
by strong aggregation-induced luminescence, were obtained through
Suzuki–Miyaura cross-coupling reactions. The reaction proved
to be straightforwardly applicable in the single amino acid synthesis
as well as in the late-stage peptide functionalization by means of
both the classical solution-phase reaction and solid-phase synthesis.
A comprehensive structural and analytical investigation highlighted
the features driving the self-assembly process and its relationship
to AIE efficiency. In particular, we showed that the simple slight
(asymmetric) extension of the TPE π-systems results in more
efficient and brighter emissions, with respect to the simple TPE system
itself.