Synthesis, spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers
Synthesis, spectroscopic properties and applications of novel N-heterocycle-containing benzotriazoles as UV absorbers
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新型N-杂环苯并三唑类紫外吸收剂的合成、光谱性质及应用
DOI：
10.1016/j.cclet.2012.06.024
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发表时间：
2012-09-01
影响因子：
9.1
通讯作者：
Chen, Wei Guo
中科院分区：
文献类型：
--
作者：
Cui, Zhi Hua;Wang, Xi Dong;Chen, Wei Guo
以4-氯-2-硝基苯胺为原料，经重氮化、偶联、还原环合、酸化等反应，合成了2种新型含氮杂环苯并三唑类化合物5-（5-氯-2-苯并三唑基）-6-羟基-1，4-二甲基-3-甲腈-2-吡啶酮（2）和4-（5-氯-2-苯并三唑基）-5-甲基-2-苯基-3-吡唑啉酮（4）。它们的结构经FT-IR、H-NMR、质谱和元素分析确证。研究了它们的光谱性质，并与常见的商业苯并三唑紫外吸收剂Tinuvin 326进行了比较。结果表明，新型含氮杂环苯并三唑类化合物在280-400 nm范围内具有尖锐的单峰，其摩尔消光系数远高于Tinuvin 326。对它们在涤纶织物上的抗紫外线防护性能进行了评价，化合物4由于其较高的上染率而远优于化合物2，这是因为化合物4具有上级。(C)2012年，崔志华。Elsevier B. V.代表中国化学会出版。All rights reserved.
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. H-1 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. (C) 2012 Zhi Hua Cui. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.