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

• DOI: 10.1021/acs.joc.1c00995
• Publication Date: 2021-07-29T17:27:53Z
• Authors: Omar Sadek; Laura Abad Galán; Frédéric Gendron; Bruno Baguenard; Stephan Guy; Amina Bensalah-Le...; Boris Le Guennic; Olivier Maury; David M. Perrin; Emmanuel Gras
• Keywords: Benzothiazole; Stereocenter; BODIPY

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