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Photostability of 4,4′‐Dihydroxythioindigo, a Mimetic of Indigo
Author(s) -
Dittmann Marc,
Graupner Franziska F.,
Maerz Benjamin,
Oesterling Sven,
de VivieRiedle Regina,
Zinth Wolfgang,
Engelhard Martin,
Lüttke Wolfgang
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201307016
Subject(s) - indigo , photochemistry , photoexcitation , intramolecular force , proton , hydrogen bond , visible spectrum , chemistry , fluorescence , materials science , excited state , organic chemistry , optoelectronics , molecule , optics , physics , atomic physics , quantum mechanics
The photochemical properties of indigo, a widely used industrial dye, has attracted both experimentalists and theoreticians from the beginning. Especially the high photostability of indigo has been the subject of intensive research. Recently, it was proposed that after photoexcitation an intramolecular proton transfer followed by a nonradiative relaxation to the ground state promote photostability. In indigo the hydrogen bond and the proton transfer occur between the opposing hemiindigo parts. Here, we provide experimental and theoretical evidence that a hydrogen transfer within one hemiindigo or hemithioindigo part is sufficient to attain photostability. This concept can serve as an interesting strategy towards new photostable dyes for the visible part of the spectrum.