陈连清,王川川,吴忠达.含苯并噻唑、喹啉单元荧光材料的合成、结构与光物理性能[J].中南民族大学学报自然科学版,2020,39(3):230-239
含苯并噻唑、喹啉单元荧光材料的合成、结构与光物理性能
Synthesis, structure and photophysical properties of fluorescent materials containing benzothiazole and quinoline units
  
DOI:10.12130/znmdzk.20200302
中文关键词: 2-芳基苯并噻唑;Jacobson环化;喹啉化合物;Friedländer缩合;有机发光材料  晶体结构
英文关键词: 2-arylbenzothiazole  Jacobson cyclization  quinoline compounds  friedländer condensation  organic light-emitting materials  crystal structure
基金项目:国家自然科学基金资助项目(31402137);湖北省杰出青年基金资助项目(2013CFA034);湖北省青年英才开发计划(RCJH15001);中央高校基本科研业务费专项资金项目(CZP17077)
作者单位
陈连清 中南民族大学 化学与材料科学学院武汉 430074 
王川川 中南民族大学 化学与材料科学学院武汉 430074 
吴忠达 中南民族大学 化学与材料科学学院武汉 430074 
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中文摘要:
      为寻找更好的发光材料, 通过Jacobson环化和缩合2-氨基硫酚及苯甲醛衍生物合成了5种甲氧基取代的2-芳基苯并噻唑;通过Friedl?nder缩合法对喹啉苯环进行有目的的调控, 合成了4种含喹啉单元的6-溴-2-芳基-4-苯基-喹啉化合物及其衍生物. 化合物通过1H NMR、质谱、元素分析等方法进行表征,证实与设计的目标产物结构相符合. 通过单晶衍射分析了2-(2,4,5-三甲氧基-苯基)-苯并噻唑,即T5的晶体结构.测试了这两类化合物的紫外-可见、荧光光谱,探讨了其光物理性能. 结果表明:改变2-芳基苯并噻唑苯环上甲氧基的取代数目、取代位置,改变喹啉单元的共轭体系大小、引入推拉电子基团,可改变化合物的发光性能,为设计合成具有优良发光性能的有机发光材料奠定了一定基础.
英文摘要:
      In order to develop better photoluminescent materials, five methoxy-substituted 2-arylbenzothiazoles were synthesized by Jacobson cyclization and condensation of 2-aminothiophenol and benzaldehyde derivatives. The quinoline benzene ring was subjected to a targeted regulation by Friedl?nder condensation method, and four kinds of 6-bromo-2-aryl-4-phenyl-quinoline compounds containing quinoline units and their derivatives were synthesized. The compounds were characterized by 1H NMR, mass spectrometry, elemental analysis and other detection methods, and their structures were consistent with the designed target compounds. The crystal structure of 2-(2,4,5-trimethoxy-phenyl)-benzothiazole (T5) was analyzed by single crystal diffraction. The UV and fluorescence spectra of these compounds were also acquired to explore their photophysical properties. The results showed that the luminescent properties of the compound could be tuned by changing the number and position of the methoxy substituents on the 2-arylbenzothiazole benzene ring, by changing the size of the conjugation system of the quinoline units, or by the introduction of strong electron withdrawing groups. Our results may serve as a reference for the design and synthesis of organic luminescent materials with excellent luminescence properties.
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