Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1462-1468.DOI: 10.6023/cjoc201712011 Previous Articles     Next Articles

Special Issue: 有机超分子化学合辑



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,
  • 基金资助:


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
  • 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).

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