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Issue 58, 2019
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Electron transfer across a spiro link: extreme solvatofluorochromism of a compact spiro-bridged N,N-dimethylaniline-phthalide dyad

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Abstract

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.

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

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Article information


Submitted
15 Apr 2019
Accepted
21 Jun 2019
First published
21 Jun 2019

Chem. Commun., 2019,55, 8414-8417
Article type
Communication

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

J. Karpiuk, P. Gawryś, E. Karpiuk and K. Suwińska, Chem. Commun., 2019, 55, 8414
DOI: 10.1039/C9CC02933H

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