Synthesis, spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers

doi:10.1016/j.cclet.2012.06.024

Chinese Chemical Letters

Volume 23, Issue 9, September 2012, Pages 1019-1022

https://doi.org/10.1016/j.cclet.2012.06.024 Get rights and content

Abstract

Two novel N-heterocycle-containing benzotriazole compounds, 5-(5-chloro-2-benzotriazolyl)-6-hydroxy-1,4-dimethyl-3-carbonitrile-2-pyridone (2) and 4-(5-chloro-2-benzotriazolyl)-5-methyl-2-phenyl-3-pyrazolone (4), were synthesized from reactant 4-chloro-2-nitroaniline via diazotization, azo coupling, reductive cyclization and acidification. Their structures were confirmed by FT-IR, ¹H NMR, mass spectroscopy and elemental analysis. Their spectral properties were investigated and compared with that of a common commercial benzotriazole UV absorber Tinuvin 326. It is found that the novel N-heterocycle-containing benzotriazole compounds exhibit sharp single peak in the range of 280–400 nm and have much higher molar extinction coefficients than that of Tinuvin 326. Their anti-UV protection properties on polyester fabric were also evaluated and compound 4 was much superior to compound 2 due to its higher exhaustion.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (Nos. 21106135 and 51173168), Zhejiang Provincial Natural Science Foundation of China (Nos. Y4090227 and Y5080021) and Zhejiang Provincial Key Innovation Team (No. 2010R50038).

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Synthesis, spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers

Abstract

Section snippets

Acknowledgments

Energy Convers. Manage.

J. Photochem. Photobiol. A: Chem.

Tetrahedron

Prog. Polym. Sci.