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An imidazoacridine-based TADF material as an effective organic photosensitizer for visible-light-promoted [2 + 2]
Ethan R Sauvé1, Don M Mayder1, Saeid Kamal1
1Department of Chemistry, The University of British Columbia 2036 Main Mall, Vancouver British Columbia V6T 1Z1 Canada zhudson@chem.ubc.ca +1-604-822-2691.
Abstract:
Energy transfer (EnT) is a fundamental activation process in visible-light-promoted photocycloaddition reactions. This work describes the performance of imidazoacridine-based TADF materials for visible-light mediated triplet-triplet EnT photocatalysis. The TADF material ACR-IMAC has been discovered as an inexpensive, high-performance organic alternative to the commonly used metal-based photosensitizers for visible-light EnT photocatalysis. The efficiency of ACR-IMAC as a photosensitizer is comparable with Ir-based photosensitizers in both intra- and intermolecular [2 + 2] cycloadditions. ACR-IMAC mediated both dearomative and non-dearomative [2 + 2] cycloadditions in good yields, with high regio- and diastereocontrol. Cyclobutane-containing bi- tri- and tetracylic scaffolds were successfully prepared, with broad tolerance toward functional groups relevant to drug discovery campaigns. Fluorescence quenching experiments, time-correlated single-photon counting, and transient absorption spectroscopy were also conducted to provide insight into the reaction and evidence for an EnT mechanism.
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