Chromogenic properties of 2-(2-carbomethoxy-3,4-dichloro-6-hydroxyphenyl)benzoxazole and its Zn(II) and Cd(II) complexes
Elena V. Vetrova
1
,
I O Tupaeva
1
,
Yu A Sayapin
2
,
E A Gusakov
1
,
Oleg N. Demidov
4
,
V. I. Minkin
1
,
Publication type: Journal Article
Publication date: 2020-09-01
scimago Q2
wos Q1
SJR: 0.680
CiteScore: 8.5
Impact factor: 4.2
ISSN: 01437208, 18733743
General Chemical Engineering
Process Chemistry and Technology
Abstract
The chromogenic properties of 2-(2-carbomethoxy-3,4-dichloro-6-hydroxyphenyl)benzoxazole (1) were studied. Solvatochromism of 1 was observed at keto-enol equilibrium due to the ground state intramolecular proton transfer (GSIPT). It was found that solvents with a good hydrogen bond acceptor (β) ability were able to stabilise the keto form of 1. The excited-state intra molecular proton transfer (ESIPT) in molecules of 1 resulted in intense fluorescence with an anomalous Stokes shift of up to 8493 cm−1 and quantum yields of 0.08–0.19. The keto-form of 1 exhibits negative T-type photochromism with a thermally reversible photoconversion to the enol form. The complexes of ligand 1 with Zn(II) and Cd(II) were synthesised. According to X-ray structural analysis, the zinc complex is the neutral complex, which is formed by two oxazole-N and two phenol O donors of ligand 1 which crystallise in a centrosymmetric group with the zinc ion located on the inversion centres. The synthesised complexes possess effective blue fluorescence and resistance to photodegradation.
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Vetrova E. V. et al. Chromogenic properties of 2-(2-carbomethoxy-3,4-dichloro-6-hydroxyphenyl)benzoxazole and its Zn(II) and Cd(II) complexes // Dyes and Pigments. 2020. Vol. 180. p. 108417.
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Vetrova E. V., Tupaeva I. O., Sayapin Yu. A., Gusakov E. A., Nikolaevskii S. A., Demidov O. N., Minkin V. I., Metelitsa A. V. Chromogenic properties of 2-(2-carbomethoxy-3,4-dichloro-6-hydroxyphenyl)benzoxazole and its Zn(II) and Cd(II) complexes // Dyes and Pigments. 2020. Vol. 180. p. 108417.
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TY - JOUR
DO - 10.1016/j.dyepig.2020.108417
UR - https://doi.org/10.1016/j.dyepig.2020.108417
TI - Chromogenic properties of 2-(2-carbomethoxy-3,4-dichloro-6-hydroxyphenyl)benzoxazole and its Zn(II) and Cd(II) complexes
T2 - Dyes and Pigments
AU - Vetrova, Elena V.
AU - Tupaeva, I O
AU - Sayapin, Yu A
AU - Gusakov, E A
AU - Nikolaevskii, Stanislav Alexandrovich
AU - Demidov, Oleg N.
AU - Minkin, V. I.
AU - Metelitsa, Anatoly V.
PY - 2020
DA - 2020/09/01
PB - Elsevier
SP - 108417
VL - 180
SN - 0143-7208
SN - 1873-3743
ER -
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@article{2020_Vetrova,
author = {Elena V. Vetrova and I O Tupaeva and Yu A Sayapin and E A Gusakov and Stanislav Alexandrovich Nikolaevskii and Oleg N. Demidov and V. I. Minkin and Anatoly V. Metelitsa},
title = {Chromogenic properties of 2-(2-carbomethoxy-3,4-dichloro-6-hydroxyphenyl)benzoxazole and its Zn(II) and Cd(II) complexes},
journal = {Dyes and Pigments},
year = {2020},
volume = {180},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.dyepig.2020.108417},
pages = {108417},
doi = {10.1016/j.dyepig.2020.108417}
}