ArticleChemical science2026
Skeletal rearrangement of [4]helicenes under acidic conditions: dynamic chirality and improved properties by subsequent peripheral editing.
Article in Chemical science, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Cationic diaza[4]helicenes are attractive fluorescent scaffolds, yet access to unsymmetrical substitution patterns remains limited. Here, we report that chiral 1,13-dimethoxyquinacridinium (DMQA) derivatives undergo an acid-mediated skeletal rearrangement after hydride or methyl addition, enabling the sequential migration of methoxy groups and providing unprecedented 1,11- and 3,11-substituted cationic [4]helicene regioisomers. Following aerobic photooxidation, the rearranged helicenes were isolated and characterized by spectroscopy, electrochemistry, crystallography, and computation. Relative to the parent 1,13-DMQA scaffold, these core-edited systems display progressive planarization, altered redox behavior, and marked hypsochromic shifts in both absorption and emission, together with improved fluorescence efficiencies. The mono-rearranged platform further enables selective peripheral editing through S
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