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Blue-Light Photocleavable Protecting Groups Based on Benzothiadiazole Scaffolds

2020    Norris, Sean; Warner, Caroline C.; Thooft, Andrea M.; Demirci, Selin K.; Lampkin, Bryan J.; Miner, Kyle; Ellern, Arkady; VanVeller, Brett

An unexpected nucleophilic aromatic substitution lead to a novel benzothiadiazole scaffold that bore the functional group pattern associated with benzyl-type photocleavable protecting groups. The new molecules display efficient photochemical release of leaving groups with blue light. The performance of both ortho- and meta-substituted derivatives was probed through both structural manipulation and computational metrics to improve performance.