Blue-Light Photocleavable Protecting Groups Based on Benzothiadiazole Scaffolds.

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.