Self-assembly of boc-protected diphenylalanine functionalized with boron-dipyrromethane

Year: 2025

Authors: Catalini S., Mancusi F., Cicchi S., Di Donato M., Iagatti A., Lapini A., Foggi P., Petrillo C., Di Michele A., Paolantoni M., Comez L., Paciaroni A.

Autors Affiliation: Univ Perugia, Dipartimento Fis & Geol, Via Pascoli, I-06123 Perugia, PG, Italy; CNR INO, Largo Fermi 6, I-50125 Florence, FI, Italy; European Lab Nonlinear Spect, Via Nello Carrara 1, I-50019 Sesto Fiorentino, FI, Italy; Univ Firenze, Dipartimento Chim Ugo Schiff, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, Italy; CNR ICCOM, Via Madonna Piano 10, I-50019 Sesto Fiorentino, FI, Italy; Univ Parma, Dip Sci Chim Vita & Sostenibil Ambientale, Parco Area Sci 17-A, I-43124 Parma, PR, Italy; Univ Perugia, Dipartimento Chim Biol & Biotecnol, Via Elce Di Sotto 8, I-06123 Perugia, PG, Italy; Univ Perugia, CNR Ist Officina Materiali IOM, Dipartimento Fis & Geol, Via Pascoli, I-06123 Perugia, PG, Italy.

Abstract: Peptides functionalized with fluorescent dyes can form aggregated structures that show potential for photonic and/or theranostic applications. In this study, we used the good-bad solvent method to induce the self-assembly of chromopeptides into various products, which were characterized using a multi-technique spectroscopic approach. Two hydrophobic chromopeptides were designed by attaching boron-dipyrromethane dyes to Bocprotected diphenylalanine, resulting in spherical aggregates with tunable dimensions, influenced by the compound’s molar concentration and solvent composition. These aggregates exhibit distinct optical properties, including bathochromic shifts in absorption and emission bands, as well as induced chirality, suggesting different chromophore orientations within the microspheres. Moreover, the aggregates show accelerated excited-state relaxation compared to monomeric chromopeptides, primarily through non-radiative processes. This work establishes a foundation for future studies focused on optimizing the desired photophysical properties of similar chromopeptide aggregates, depending on their intended application.

Journal/Review: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY

Volume: 340      Pages from: 126362-1  to: 126362-11

More Information: S.C. and A.P. thank the research project FSE-REACT EU financed by National Social Fund-National Operative Research Program and Innovation 2014-2020 (D.M. 1062/2021) , personal Grant number 23-G-15445-3. S.C., P.F., C.P., A.D.M., M.P., L.C. and A.P. thank the European Union-NextGenerationEU project under the Italian Ministry of University and Research (MUR) National Innovation Ecosystem grant ECS00000041-VITALITY-CUP: J97G22000170005 and B43C22000470005. L.C., A. I., and A. L. thank Ministero dell’Istruzione dell’Universita e della Ricerca Italiano for the financial support of the project LANTERN (PRIN2022-20225NPY8P) . S.C. and F.M. thank the European UnionNextGeneration EU programme in the context of the National Recovery and Resilience Plan, Mission 4, Component 2,Investment 1.5, ECS00000017, THE Tuscany Health Ecosystem-Spoke 4 Nanotechnologies for diagnosis and therapy, CUP: B83C22003920001.
KeyWords: Chromopeptides; Self-assembly; Microparticles; Diphenylalanine; Supramolecular aggregates
DOI: 10.1016/j.saa.2025.126362