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

doi:10.6023/cjoc201712011

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

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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

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 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

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).

1. Synthesis and Fluorescent Property of Benzo [c]coumarin Carboxylic Derivatives.PDF(690KB)

Abstract

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.

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

Cite this article

Shi Juan, Zhang Zunting. Synthesis and Fluorescent Property of Benzo [c]coumarin Carboxylic Derivatives[J]. Chin. J. Org. Chem., 2018, 38(6): 1462-1468.

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[1] Hu, B. B.; Lu, P.; Wang, Y. G. New J. Chem. 2013, 37, 1645.
[2] Yu, C.; Zhang, J.; Chen, L.; Li, J.; Liu, P.; Wang, W.; Yan, B. Talanta 2011, 85, 1627.
[3] Lee, E. Y.; Jang, S. Y.; Suh, M. P. J. Am. Chem. Soc. 2005, 127, 6374.
[4] Hisaki, I.; Kometani, E.; Shigemitsu, H.; Saeki, A.; Seki, S.; Tohnai, N.; Miyata, M. Cryst. Growth Des. 2011, 11, 5488.
[5] Seth, D. K.; Sakar, D.; Kar, T. CrystEngComm 2011, 13, 4528.
[6] Zhou, T. L.; Jia, T.; Zhao, S. S.; Guo, J. H.; Zhang, H. Y.; Wang, Y. Cryst. Growth Des. 2012, 12, 179.
[7] Ito, H.; Iguchi, A.; Hatano, T. J. Agric. Food Chem. 2008, 56, 393.
[8] Bialonska, D.; Kasimsetty, S. G.; Khan, S. I.; Ferreira, D. J. Agric. Food Chem. 2009, 57, 10181.
[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.
[10] Pandey, J.; Jha, A. K.; Hajela, K. Bioorg. Med. Chem. 2004, 12, 2239.
[11] Appel, B.; Saleh, N. N. R.; Langer, P. Chem.-Eur. J. 2006, 12, 1221.
[12] Nguyen, V. T. H.; Langer, P. Tetrahedron Lett. 2005, 46, 1013.
[13] Ullah, E.; Appel, B.; Fischer, C.; Langer, P. Tetrahedron 2006, 62, 9694.
[14] Nikolov, P.; Petkov, I.; Marko, P. Z. Naturforsch. 2000, 55a, 741.
[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). (陈超越, 胡劲松, 柴飞飞, 谢凯云, 张晓梅, 石建军, 结构化学, 2014, 33, 395.)
[16] Tasior, M.; Kim, D.; Singha, S.; Krzeszewski, M.; Ahn, K. H.; Gryko, D. T. J. Mater. Chem. C 2015, 3, 1421.
[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.
[18] Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. 1995, 34, 1555.
[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). (孙静波, 张恭贺, 贾小宇, 薛鹏冲, 贾俊辉, 卢然, 化学学报, 2016, 74, 165.)
[20] Feng, Q.; Wang, M.; Dong, B.; Xu, C.; Zhao, J.; Zhang, H. CrystEngComm 2013, 15, 3623.
[21] Cheng, X.; Wang, K.; Huang, S.; Zhang, H. Y.; Zhang, H. Y.; Wang, Y. Angew. Chem., Int. Ed. 2015, 54, 1.
[22] Yu, T. Z.; Zhao, Y. L.; Fan, D. W. J. Mol. Struct. 2006, 1~3, 18.
[23] Sheldrick, G. M. SHELXS-97, Program for X-Ray Crystal Structure Solution, University of Götingen, Germany, 2007.
[24] Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112.

苯并香豆素羧酸衍生物的合成及荧光性能研究

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

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