Chiral Benzothiazole Monofluoroborate Featuring Chiroptical and Oxygen-Sensitizing Properties: Synthesis and Photophysical Studies

Omar Sadek (1) , Laura Abad Galán (2) , Frédéric Gendron (3) , Bruno Baguenard (4) , Stephan Guy (4) , Amina Bensalah (4) , Boris Le Guennic (3) , Olivier Maury (2) , David M Perrin (5) , Emmanuel Gras (1)

1 LCC - Laboratoire de chimie de coordination
2 LC - Laboratoire de Chimie - UMR5182
3 ISCR - Institut des Sciences Chimiques de Rennes
4 iLM - MNP - iLM - Matériaux et nanostructures photoniques
5 UBC - University of British Columbia

Advances in personalized medicine are prompting the development of multimodal agents, that is, molecules that combine properties promoting various diagnostic and therapeutic applications. General approaches exploit chemical conjugation of therapeutic agents with contrast agents or the design of multimodal nanoplatforms. Herein, we report the design of a single molecule that exhibits potential for different diagnostic modes as well as the ability to sensitize oxygen, thus offering potential for photodynamic therapy. Exceptionally, this work involves the synthesis and chiral resolution of an enantiomeric pair of chiral monofluoroborates that contain a stereogenic boron atom. Combining experimental and theoretical chiroptical studies allowed the unambiguous determination of their absolute configuration. Photophysical investigations established the ability of this compound to sensitize oxygen even in the absence of heavy atoms within its structure. The synthesis of a chiral benzothiazole monofluoroborate paves a way to multimodal diagnostic tools (fluorescence and nuclear imaging) while also featuring potential therapeutic applications owing to its ability to activate oxygen to its singlet state for use in photodynamic therapy.

Mots clés: Absorption; Ligands; Mixtures; Boron; Molecular structure

Domaines: Chimie; Chimie organique

Omar Sadek, Laura Abad Galán, Frédéric Gendron, Bruno Baguenard, Stephan Guy, et al.. Chiral Benzothiazole Monofluoroborate Featuring Chiroptical and Oxygen-Sensitizing Properties: Synthesis and Photophysical Studies. Journal of Organic Chemistry, 2021, 86 (86), pp.17. ⟨10.1021/acs.joc.1c00995⟩. ⟨hal-03333839⟩