Graphene Oxide-BODIPY Conjugates as Highly Fluorescent Materials

Reina G, Beneventi GM, Kaur R, Biagiotti G, Cadranel A, Ménard-Moyon C, Nishina Y, Richichi B, Guldi DM, Bianco A (2023)

Publication Type: Journal article

Publication year: 2023

Journal

DOI: 10.1002/chem.202300266

Abstract

Covalent functionalization of graphene oxide (GO) with boron dipyrromethenes (BODIPYs) was achieved through a facile synthesis, affording two different GO-BODIPY conjugates where the main difference lies in the nature of the spacer and the type of bonds between the two components. The use of a long but flexible spacer afforded strong electronic GO-BODIPY interactions in the ground state. This drastically altered the light absorption of the BODIPY structure and impeded its selective excitation. In contrast, the utilisation of a short, but rigid spacer based on boronic esters resulted in a perpendicular geometry of the phenyl boronic acid BODIPY (PBA-BODIPY) with respect to the GO plane, which enables only minor electronic GO-BODIPY interactions in the ground state. In this case, selective excitation of PBA-BODIPY was easily achieved, allowing to investigate the excited state interactions. A quantitative ultrafast energy transfer from PBA-BODIPY to GO was observed. Furthermore, due to the reversible dynamic nature of the covalent GO-PBA-BODIPY linkage, some PBA-BODIPY is free in solution and, hence, not quenched from GO. This resulted in a weak, but detectable fluorescence from the PBA-BODIPY that will allow to exploit GO-PBA-BODIPY for slow release and imaging purposes.

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Additional Organisation(s)

Involved external institutions

Immunologie, Immunopathologie et Chimie Thérapeutique (I2CT) France (FR) Università degli Studi di Firenze / University of Florence Italy (IT) Okayama University / 岡山大学 Japan (JP)

How to cite

APA:

Reina, G., Beneventi, G.M., Kaur, R., Biagiotti, G., Cadranel, A., Ménard-Moyon, C.,... Bianco, A. (2023). Graphene Oxide-BODIPY Conjugates as Highly Fluorescent Materials. Chemistry - A European Journal. https://dx.doi.org/10.1002/chem.202300266

MLA:

Reina, Giacomo, et al. "Graphene Oxide-BODIPY Conjugates as Highly Fluorescent Materials." Chemistry - A European Journal (2023).

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