Synthesis, characterization, and crystal structure of modified benzophenone UV-absorber containing reactive group

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• 作者：Yun Shen ; Jianhua Zhu ; Hongxia Chen ; Dan Huang
• 关键词：UV absorber ; Synthesis ; X ; ray structure ; (4 ; (4 ; 6 ; Dichloro ; 1 ; 3 ; 5 ; triazin ; 2 ; yloxy) ; 2 ; hydroxyphenyl)phenyl)methanone
• 刊名：Research on Chemical Intermediates
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：42
• 期：4
• 页码：2909-2918
• 全文大小：806 KB
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• 作者单位：Yun Shen (1) (4)
  Jianhua Zhu (2)
  Hongxia Chen (3)
  Dan Huang (1) (4)
  
  1. Key Laboratory of Eco-Textile (Jiangnan University) of Ministry of Education, Wuxi, 214112, China
  4. College of Textiles and Clothing, Jiangnan University, 1800 Lihu Road, Wuxi, 214112, Jiangsu Province, China
  2. Yancheng Institute of Health Sciences, College of Pharmaceuticals, Yanchen, 224005, China
  3. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675

文摘

A modified benzophenone UV-absorber containing reactive group (4-(4,6-dichloro-1,3,5-triazin-2-yloxy)-2-hydroxyphenyl)phenyl)methanone (UV-DTHM) has been prepared in good yield from the nucleophilic substitution reaction of 2,4-dihydroxy benzophenone with 2,4,6-trichlorotriazine, catalyzed by 1.3 equiv. NaOH. The most favorable reaction conditions (the catalyst dosage, the mole ratio of the reactants, and reactive time) were selected. The compound was characterized by IR spectroscopy, 1H NMR, 13C NMR, mass spectrometry, elemental analysis, and single crystal X-ray diffraction. The crystal monoclinic, space group C c with the unit cell parameters a = 3.987(2), b = 30.688(16), c = 12.423(6) Å and α = 90.00, β = 92.117(15), γ = 90.00º, Z = 4, R = 0.0620. wR(F 2) = 0.1589. The crystal structure reveals that 2,4,6-trichlorotriazine is boned to 4-seat hydroxyl of 2,4-dihydroxy benzophenone and a intramolecular hydrogen bond is formed with hydrogen of 2-hydroxyl and oxygen of carbonyl group. Moreover, thermogravimetric analysis (TGA) of UV-DTHM was studied, showing two distinct endothermic peaks at temperatures of 281.5 and 358.5 °C. The molar absorption coefficient of UV-DTHM is 1.6 × 104 and 6.3 × 103 at 268 and 330 nm, respectively, and shows excellent ultraviolet absorption property.