Antoniou Antonia I, Pesenti Michela, Crespi Stefania, Shenoy Dhriti S, Penconi Marta, Bossi Alberto, Pellegrino Sara
Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, IT-20133 Milan, Italy.
Dipartimento di Scienze della Terra Ardito Desio, Università degli Studi di Milano, IT-20133 Milan, Italy.
J Org Chem. 2024 Apr 5;89(7):4733-4740. doi: 10.1021/acs.joc.3c02969. Epub 2024 Mar 23.
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.
