Aggregation-Induced Enhanced Emission of Tetraphenylethene-phenylalanine Hybrids: Synthesis and Characterization

• Published in: Journal of organic chemistry 2024-04, Vol.89 (7), p.4733-4740
• Main Authors: Antoniou, Antonia I., Pesenti, Michela, Crespi, Stefania, Shenoy, Dhriti S., Penconi, Marta, Bossi, Alberto, Pellegrino, Sara
• Format: Article
• Language: English
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.3c02969

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.