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 pi-systems results in more efficient and brighter emissions, with respect to the simple TPE system itself.

Aggregation-Induced Enhanced Emission of Tetraphenylethene-phenylalanine Hybrids: Synthesis and Characterization / A.I. Antoniou, M. Pesenti, S. Crespi, D.S. Shenoy, M. Penconi, A. Bossi, S. Pellegrino. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 89:7(2024 Apr 05), pp. 4733-4740. [10.1021/acs.joc.3c02969]

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

S. Crespi;D.S. Shenoy;S. Pellegrino
2024

Abstract

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 pi-systems results in more efficient and brighter emissions, with respect to the simple TPE system itself.
Settore CHIM/06 - Chimica Organica
   Functional Nano-Scaffolds for Regenerative Medicine
   NANOREMEDI
   European Commission
   Horizon Europe Framework Programme
   101072645
5-apr-2024
23-mar-2024
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/1045588
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