Intramolecular electron transfer over the sp-C-link in dimethyl-aniline-spiro-phthalide leads to extreme solvatofluorochromism (11 600 cm) and a fluorescence maximum shift from 357 (hexane) to 595 nm (acetonitrile). The spiro link enhances π-σ* negative hyperconjugation leading to C-O bond elongation and electron transfer over a longer distance than in a non-spirocyclic analogue.
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