Citation: 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 shu

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

Shi Juan ^a,b ,
Zhang Zunting ^b,,

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

Corresponding author: Zhang Zunting, zhangzunting@sina.com
Received Date: 6 December 2017
Revised Date: 28 January 2018
Available Online: 11 June 2018
Fund Project: the Scientific Research Program Funded by Shaanxi Provincial Education Department 17JS026Project 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)the National Natural Science Foundation of China 21373132the National Natural Science Foundation of China 21542002the Innovation Funds of Graduate Programs of Shaanxi Normal University 2013CXB026

Figures(9)

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 (Ф_F=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.
- benzo[c]coumarin carboxylic acid,
- crystal structure,
- dimer,
- fluorescent property
1. [1]
  Hu, B. B.; Lu, P.; Wang, Y. G. New J. Chem. 2013, 37, 1645. doi: 10.1039/c2nj41063j
2. [2]
  Yu, C.; Zhang, J.; Chen, L.; Li, J.; Liu, P.; Wang, W.; Yan, B. Talanta 2011, 85, 1627. doi: 10.1016/j.talanta.2011.06.057
3. [3]
  Lee, E. Y.; Jang, S. Y.; Suh, M. P. J. Am. Chem. Soc. 2005, 127, 6374. doi: 10.1021/ja043756x
4. [4]
  Hisaki, I.; Kometani, E.; Shigemitsu, H.; Saeki, A.; Seki, S.; Tohnai, N.; Miyata, M. Cryst. Growth Des. 2011, 11, 5488. doi: 10.1021/cg201075z
5. [5]
  Seth, D. K.; Sakar, D.; Kar, T. CrystEngComm 2011, 13, 4528. doi: 10.1039/c1ce05037k
6. [6]
  Zhou, T. L.; Jia, T.; Zhao, S. S.; Guo, J. H.; Zhang, H. Y.; Wang, Y. Cryst. Growth Des. 2012, 12, 179. doi: 10.1021/cg200920d
7. [7]
  Ito, H.; Iguchi, A.; Hatano, T. J. Agric. Food Chem. 2008, 56, 393. doi: 10.1021/jf0726942
8. [8]
  Bialonska, D.; Kasimsetty, S. G.; Khan, S. I.; Ferreira, D. J. Agric. Food Chem. 2009, 57, 10181. doi: 10.1021/jf9025794
9. [9]
  Schmidt, J. M.; Tremblay, G. B.; Page, M.; Mercure, J.; Feher, M.; Dunn-Dufault, R.; Peter, M. G.; Redden, P. R. J. Med. Chem. 2003, 46, 1289. doi: 10.1021/jm034007d
10. [10]
  Pandey, J.; Jha, A. K.; Hajela, K. Bioorg. Med. Chem. 2004, 12, 2239. doi: 10.1016/j.bmc.2004.02.018
11. [11]
  Appel, B.; Saleh, N. N. R.; Langer, P. Chem.-Eur. J. 2006, 12, 1221. doi: 10.1002/(ISSN)1521-3765
12. [12]
  Nguyen, V. T. H.; Langer, P. Tetrahedron Lett. 2005, 46, 1013. doi: 10.1016/j.tetlet.2004.12.030
13. [13]
  Ullah, E.; Appel, B.; Fischer, C.; Langer, P. Tetrahedron 2006, 62, 9694. doi: 10.1016/j.tet.2006.07.084
14. [14]
  Nikolov, P.; Petkov, I.; Marko, P. Z. Naturforsch. 2000, 55a, 741.
15. [15]
  Chen, C. Y.; Hu, J. S.; Chai, F. F.; Yun, X. K.; Zhang, X. M.; Shi, J. J. Chin. J. Struct. Chem. 2014, 33, 395(in Chinese).
16. [16]
  Tasior, M.; Kim, D.; Singha, S.; Krzeszewski, M.; Ahn, K. H.; Gryko, D. T. J. Mater. Chem. C 2015, 3, 1421.
17. [17]
  Jiao, L.; Wu, Y.; Ding, Y.; Wang, S.; Zhang, P.; Yu, C.; Wei, Y.; Mu, X.; Hao, E. Chem.-Asian J. 2014, 9, 805. doi: 10.1002/asia.v9.3
18. [18]
  Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. 1995, 34, 1555. doi: 10.1002/(ISSN)1521-3773
19. [19]
  Sun, J. B.; Zhang, G. H.; Jia, X. Y.; Xue, P. C.; Jia, J. P.; Lu, R. Acta Chim. Sinica 2016, 74, 165(in Chinese).
20. [20]
  Feng, Q.; Wang, M.; Dong, B.; Xu, C.; Zhao, J.; Zhang, H. CrystEngComm 2013, 15, 3623. doi: 10.1039/c3ce27102a
21. [21]
  Cheng, X.; Wang, K.; Huang, S.; Zhang, H. Y.; Zhang, H. Y.; Wang, Y. Angew. Chem., Int. Ed. 2015, 54, 1. doi: 10.1002/anie.201410930
22. [22]
  Yu, T. Z.; Zhao, Y. L.; Fan, D. W. J. Mol. Struct. 2006, 1~3, 18.
23. [23]
  Sheldrick, G. M. SHELXS-97, Program for X-Ray Crystal Structure Solution, University of Götingen, Germany, 2007.
24. [24]
  Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112.
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