PubAg

Main content area

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

Author:
Karpiuk, Jerzy, Gawryś, Paweł, Karpiuk, Elena, Suwińska, Kinga
Source:
Chemical communications 2019 v.55 no.58 pp. 8414-8417
ISSN:
1364-548X
Subject:
acetonitrile, chemical bonding, electron transfer, fluorescence, hexane
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.
Agid:
6539530