Electron transfer across a spiro link: extreme solvatofluorochromism of a compact spiro-bridged N,N-dimethylaniline-phthalide dyad

Intramolecular electron transfer over the sp3-C-link in dimethyl-aniline-spiro-phthalide leads to extreme solvatofluorochromism (11 600 cm-1) 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 elonga...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-07, Vol.55 (58), p.8414-8417
Main Authors: Karpiuk, Jerzy, Gawryś, Paweł, Karpiuk, Elena, Suwińska, Kinga
Format: Article
Language:English
Subjects:
Acetonitrile
Aniline
Crystallography
Electron transfer
Electrons
Elongation
Fluorescence
NMR
Nuclear magnetic resonance
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Summary:Intramolecular electron transfer over the sp3-C-link in dimethyl-aniline-spiro-phthalide leads to extreme solvatofluorochromism (11 600 cm-1) 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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc02933h