有机化学 ›› 2018, Vol. 38 ›› Issue (6): 1462-1468.DOI: 10.6023/cjoc201712011 上一篇    下一篇

所属专题: 有机超分子化学合辑

研究论文

苯并香豆素羧酸衍生物的合成及荧光性能研究

史娟a,b, 张尊听b   

  1. a 陕西师范大学化学化工学院 教育部药用资源与天然药物化学重点实验室 西北濒危药材资源开发国家工程实验室 西安 710062;
    b 陕西理工大学化学与环境科学学院 陕西省催化重点实验室 汉中 723001
  • 收稿日期:2017-12-06 修回日期:2018-01-28 发布日期:2018-02-11
  • 通讯作者: 张尊听,E-mail:zhangzunting@sina.com E-mail:zhangzunting@sina.com
  • 基金资助:

    国家自然科学基金(Nos.21373132,21542002)、陕西省教育厅科学研究(No.17JS026)和陕西师范大学研究生创新基金(No.2013CXB026)资助项目.

Synthesis and Fluorescent Property of Benzo [c]coumarin Carboxylic Derivatives

Shi Juana,b, Zhang Zuntingb   

  1. a Key Laboratory of Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062;
    b Shaanxi Key Laboratory of Catalysis, School of Chemical and Environmental Sciences, Shaanxi University of Technology, Hanzhong 723001
  • Received:2017-12-06 Revised:2018-01-28 Published:2018-02-11
  • Contact: 10.6023/cjoc201712011 E-mail:zhangzunting@sina.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21373132, 21542002), the Scientific Research Program Funded by Shaanxi Provincial Education Department (No. 17JS026) and the Innovation Funds of Graduate Programs of Shaanxi Normal University (No. 2013CXB026).

合成了具有较高荧光性能的香豆素衍生物:7-羟基-6-氧代-6H-苯并香豆素-8-羧酸(3a)及2,3-苯并-7-羟基-6-氧代-6H-苯并香豆素-8-羧酸(3b),通过单晶X射线衍射对化合物结构进行了表征.3a3b在乙醇溶液、晶体结构下具有较高的荧光量子产率(ФF).3a晶体结构存在羧酸二聚体,较强的分子间作用力使其荧光量子效率可达0.32,组成二聚体单元的所有原子处在同一平面内,3a的分子刚性较强.二聚体单元间则通过C—H…O分子间氢键以边对面的堆积方式相连.

关键词: 苯并香豆素羧酸衍生物, 晶体结构, 二聚体, 荧光性能

Two fluorescent compounds, 7-hydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid (3a) and 2,3-benzo[f]-7-hydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid (3b) have been synthesized and characterized by the method of X-ray single crystal diffraction. 3a and 3b show high fluorescence quantum efficiency in both ethanol solution and solid state. In the crystal-state, dimerization of carboxylic group and intermolecular interaction lead to 3a owned a high fluorescence quantum efficiency (ФF=0.32). The dimers existing in 3a crystal lattice, are composed of carboxylic acid groups and have strong intermolecular interactions (bond lengths are 0.1870 nm, bond angles are 166.8°). All the atoms in dimer are nearly coplanar, showing extremely strong plane rigidity. The dimers are connected by C-H…O intermolecular hydrogen bonds, and the edge-to-face stackings exist in neighbor dimers.

Key words: benzo[c]coumarin carboxylic acid, crystal structure, dimer, fluorescent property