The tautomerism of 8-(phenyldiazenyl)quinolin-5-ol has been studied by a combination of theoretical (DFT calculations) and experimental (UV-Vis and NMR) methods. The detailed study of neutral molecules has shown that the hydrazone tautomeric form, stabilized by an intramolecular N-HMIDLINE HORIZONTAL ELLIPSISN hydrogen bond, is solely present in most of the solvents. In strong proton acceptor solvents, besides the dominant hydrazone form, the deprotonated form also appears. Solvent effects on the absorption maxima of the hydrazone form are interpreted by the linear solvation energy relationship concept, using Kamlet-Taft and Catalan models. Upon deprotonation, a substantial structural transformation is observed in the studied compound leading to a slow rotation around the Cquin-N bond. The process, as monitored by 1H NMR, is strongly solvent assisted and facilitated by proton acceptor solvents. Consequently, the investigated dye could be considered as a base-activated rotary switch.
TY - JOUR
AU - Lađarević, Jelena
AU - Mijin, Dušan
AU - Antonov, Liudmil
PY - 2020
UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4380
AB - The tautomerism of 8-(phenyldiazenyl)quinolin-5-ol has been studied by a combination of theoretical (DFT calculations) and experimental (UV-Vis and NMR) methods. The detailed study of neutral molecules has shown that the hydrazone tautomeric form, stabilized by an intramolecular N-HMIDLINE HORIZONTAL ELLIPSISN hydrogen bond, is solely present in most of the solvents. In strong proton acceptor solvents, besides the dominant hydrazone form, the deprotonated form also appears. Solvent effects on the absorption maxima of the hydrazone form are interpreted by the linear solvation energy relationship concept, using Kamlet-Taft and Catalan models. Upon deprotonation, a substantial structural transformation is observed in the studied compound leading to a slow rotation around the Cquin-N bond. The process, as monitored by 1H NMR, is strongly solvent assisted and facilitated by proton acceptor solvents. Consequently, the investigated dye could be considered as a base-activated rotary switch.
PB - Elsevier Sci Ltd, Oxford
T2 - Dyes and Pigments
T1 - Tautomerism in 8-(phenyldiazenyl)quinolin-5-ol: An attempt for pH activated rotary switch
VL - 182
DO - 10.1016/j.dyepig.2020.108628
ER -
@article{
author = "Lađarević, Jelena and Mijin, Dušan and Antonov, Liudmil",
year = "2020",
abstract = "The tautomerism of 8-(phenyldiazenyl)quinolin-5-ol has been studied by a combination of theoretical (DFT calculations) and experimental (UV-Vis and NMR) methods. The detailed study of neutral molecules has shown that the hydrazone tautomeric form, stabilized by an intramolecular N-HMIDLINE HORIZONTAL ELLIPSISN hydrogen bond, is solely present in most of the solvents. In strong proton acceptor solvents, besides the dominant hydrazone form, the deprotonated form also appears. Solvent effects on the absorption maxima of the hydrazone form are interpreted by the linear solvation energy relationship concept, using Kamlet-Taft and Catalan models. Upon deprotonation, a substantial structural transformation is observed in the studied compound leading to a slow rotation around the Cquin-N bond. The process, as monitored by 1H NMR, is strongly solvent assisted and facilitated by proton acceptor solvents. Consequently, the investigated dye could be considered as a base-activated rotary switch.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Dyes and Pigments",
title = "Tautomerism in 8-(phenyldiazenyl)quinolin-5-ol: An attempt for pH activated rotary switch",
volume = "182",
doi = "10.1016/j.dyepig.2020.108628"
}
Lađarević, J., Mijin, D.,& Antonov, L.. (2020). Tautomerism in 8-(phenyldiazenyl)quinolin-5-ol: An attempt for pH activated rotary switch. in Dyes and Pigments
Elsevier Sci Ltd, Oxford., 182.
https://doi.org/10.1016/j.dyepig.2020.108628
Lađarević J, Mijin D, Antonov L. Tautomerism in 8-(phenyldiazenyl)quinolin-5-ol: An attempt for pH activated rotary switch. in Dyes and Pigments. 2020;182.
doi:10.1016/j.dyepig.2020.108628 .
Lađarević, Jelena, Mijin, Dušan, Antonov, Liudmil, "Tautomerism in 8-(phenyldiazenyl)quinolin-5-ol: An attempt for pH activated rotary switch" in Dyes and Pigments, 182 (2020),
https://doi.org/10.1016/j.dyepig.2020.108628 . .
