Chinese Journal of Organic Chemistry >
Synthesis and Fluorescent Property of Benzo [c]coumarin Carboxylic Derivatives
Received date: 2017-12-06
Revised date: 2018-01-28
Online published: 2018-02-11
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.
Shi Juan , Zhang Zunting . Synthesis and Fluorescent Property of Benzo [c]coumarin Carboxylic Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(6) : 1462 -1468 . DOI: 10.6023/cjoc201712011
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