Aggregation Control of Hemicyanine Fluorescent Dye by Using of Cucurbit[7]uril and Pillar[6]arene
Meijiao Cao
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorFang Hu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorXie Han
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorYufeng Zhang
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorDi Wu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorSheng Hua Liu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorCorresponding Author
Jun Yin
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China, Tel.: Tel.: 0086-027-67867725; Fax: 0086-027-67867725Search for more papers by this authorMeijiao Cao
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorFang Hu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorXie Han
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorYufeng Zhang
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorDi Wu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorSheng Hua Liu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Search for more papers by this authorCorresponding Author
Jun Yin
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China, Tel.: Tel.: 0086-027-67867725; Fax: 0086-027-67867725Search for more papers by this authorAbstract
The aggregation of cyanine-based fluorescent dyes easily results in the fluorescence quenching, which limits the applications in biological science and materials science. So developing an efficient method to adjust the aggregation of cyanine dyes is very significant. In this work, we employ two different macrocyclic hosts pillar[6]arene (DEP[6]) and cucurbit[7]uril (CB[7]) to investigate their effects towards fluorescence spectra of dye 1. The result indicates that both of them can disrupt the aggregation of dye 1, resulting in the enhancement of its fluorescence intensity. Interestingly, investigation on the corresponding titration experiments of 1H NMR and density functional theory calculations shows that CB[7] and DEP[6] play different roles in the process of disaggregation.
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REFERENCES
- 1 Mishra, A.; Behera, R. K.; Behera, P. K.; Mishra, B. K.; Behera, G. B.. Chem. Rev., 2000, 100, 1973.
- 2 Gadde, S.; Batchelor, E. K.; Weiss, J. P.; Ling, Y. H.; Kaifer, A. E.. J. Am. Chem. Soc., 2008, 130, 17114.
- 3a Yang, H.; Yuan, B.; Zhang, X.. Acc. Chem. Res., 2014, 47, 2106.
- 3b Hu, Q. D.; Tang, G. P.; Chu, P. K.. Acc. Chem. Res., 2014, 47, 2017.
- 3c Zhang, M. M.; Yan, X. Z.; Huang, F. H.; Niu, Z. B.; Gibson, H. W.. Acc. Chem. Res., 2014, 47, 1995.
- 3d Dong, S. Y.; Zheng, B.; Wang, F.; Huang, F. H.. Acc. Chem. Res., 2014, 47, 1982.
- 3e Zhang, D. W.; Zhao, Z.; Li, Z. T.. Acc. Chem. Res., 2014, 47, 1961.
- 3f Yang, Y. W.; Sun, Y. L.; Song, N.. Acc. Chem. Res., 2014, 47, 1950.
- 3g Langton, M. J.; Beer, P. D.. Acc. Chem. Res., 2014, 47, 1935.
- 4a Liu, G. X.; Li, Z. Y.; Wu, D.; Xue, W.; Li, T. T.; Liu, S. H.; Yin, J.. J. Org. Chem., 2014, 79, 643.
- 4b Li, Z. Y.; Hu, F.; Liu, G. X.; Xue, W.; Chen, X. Q.; Liu, S. H.; Yin, Y.. Org. Biomol. Chem., 2014, 12, 7702.
- 4c Hu, F.; Huang, J. H.; Cao, M. J.; Chen, Z.; Yang, Y. W.; Liu, S. H.; Yin, J.. Org. Biomol. Chem., 2014, 12, 7712.
- 5 Biedermann, F.; Elmalem, E.; Ghosh, I.; Nau, W. M.; Scherman, O. A.. Angew. Chem., Int. Ed., 2012, 51, 7739.
- 6a Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y.. J. Am. Chem. Soc., 2008, 130, 5022.
- 6b Zhou, T.; Yu, H.; Liu, M. Q.; Yang, Y. W.. Chin. J. Chem., 2014, 32, 128.
- 6c Liu, L. Z.; Chen, Y.; Wang, L. Y.; Meier, H.; Cao, D. R.. Chin. J. Chem., 2013, 31, 624.
- 6d Zhang, F.; Cao, X. L.; Tian, D. M.; Li, H. B.. Chin. J. Chem., 2015, DOI: 10.1002/cjoc.201400675.
- 6e Zhou, Y. J.; Yao, Y.; Huang, F. H.. Chin. J. Chem., 2015, DOI: 10.1002/cjoc.201400697.
- 6f Pan, M. G.; Xue, M.. Chin. J. Chem., 2014, 32, 128.
- 7a Xue, M.; Yang, Y.; Chi, X. D.; Zhang, Z. B.; Huang, F. H.. Acc. Chem. Res., 2012, 45, 1294.
- 7b Cragg, P. J.; Sharma, K.. Chem. Soc. Rev., 2012, 41, 597.
- 7c Zhang, H. C.; Zhao, Y. L.. Chem. Eur. J., 2013, 19, 16862.
- 7d Ogoshi, T.; Yamagishi, T. A.. Eur. J. Org. Chem., 2013, 2961.
- 7e Strutt, N. L.; Zhang, H. C.; Schneebeli, S. T.; Stoddart, J. F.. Acc. Chem. Res., 2014, 47, 2631.
- 7f Cao, D.; Meier, H.. Asian J. Org. Chem., 2014, 3, 244.
- 7g Ogoshi, T.; Yamagishi, T.. Chem. Commun., 2014, 50, 4776.
- 7h Li, C. J.. Chem. Commun., 2014, 50, 12420.
- 7i Song, N.; Yang, Y. W.. Sci China Chem., 2014, 57, 1185.
- 7j Wu, X.; Duan, Q. P.; Ni, M. F.; Hu, X. Y.; Wang, L. Y.. Chin. J. Org. Chem., 2014, 34, 437.
- 7k Yue, S. Y.; Zhou, Y. J.; Yao, Y.; Xue, M.. Acta Chim. Sinica, 2014, 72, 1053.
- 7l Tan, L. L.; Yang, Y. W.. J. Incl. Phenom. Macrocycl. Chem., 2015, 81, 13.
- 7m Tan, L. L.; Li, H. W.; Qiu, Y. C.; Chen, D. X.; Wang, X.; Pan, R. Y.; Wang, Y.; Zhang, S. X.-A.; Wang, B.; Yang, Y. W.. Chem. Sci., 2015, DOI: 10.1039/C4SC03749A.
- 7n Tan, L. L.; Li, H.; Tao, Y.; Zhang, S. X.-A.; Wang, B.; Yang, Y. W.. Adv. Mater., 2014, 26, 7027.
- 7o Zhou, T.; Yu, H.; Liu, M. Q.; Yang, Y. W.. Chin. J. Chem., 2015, 33, 125.
- 7p Li, H.; Chen, D.-X.; Sun, Y.-L.; Zheng, Y. B.; Tan, L.-L.; Weiss, P. S.; Yang, Y.-W.. J. Am. Chem. Soc., 2013, 135, 1570.
- 7q Chen, D.-X.; Sun, Y.-L.; Zhang, Y.; Cui, J.-Y.; Shen, F.-Z.; Yang, Y.-W.. RSC Adv., 2013, 3, 5765.
- 8a Dsouza, R. N.; Pischel, U.; Nau, W. M.. Chem. Rev., 2011, 111, 7941.
- 8b Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L.. Angew. Chem., Int. Ed., 2005, 44, 4844.
- 8c Li, Q.-L.; Sun, Y.; Sun, Y. L.; Wen, J.; Zhou, Y.; Bing, Q.; Isaacs, L.; Jin, Y.; Gao, H.; Yang, Y. W.. Chem. Mater., 2014, 26, 6418.
- 9 Li, C.; Shu, X.; Li, J.; Fan, J.; Chen, Z.; Weng, L.; Jia, X.. Org. Lett., 2012, 14, 4126.
- 10a Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier, H.. Angew. Chem., Int. Ed., 2009, 48, 9721.
- 10b Tao, H. Q.; Cao, D. R.; Liu, L. Z.; Kou, Y. H.; Wang, L. Y.; Meier, H.. Sci. China Chem., 2012, 55, 223.
- 11a Zyss, J.; Isabelle Ledoux-Rak, I.; Weiss, H.; Bläser, D.; Boese, R.; Thallapally, P. K.; Thalladi, V. R.; Desiraju, G. R.. Chem. Mater., 2003, 15, 3063.
- 11b Chi, X.; Besnard, C.; Thorsm?lle, V. K.; Butko, V. Y.; Taylor, A. J.; Siegrist, T.; Ramirez, A. P.. Chem. Mater., 2004, 16, 5751.
- 11c Alvey, P. M.; Reczek, J. J.; Lynch, V.; Iverson, B. L.. J. Org. Chem., 2010, 75, 7682.
- 11d Klivansky, L. M.; Hanifi, D.; Koshkakaryan, G.; Holycross, D. R.; Gorski, E. K.; Wu, Q.; Chai, M. H.; Liu, Y.. Chem. Sci., 2012, 3, 2009.
- 11e Das, A.; Molla, M. R.; Maity, B.; Koley, D.; Ghosh, S.. Chem. Eur. J., 2012, 18, 9849.
- 12a Yin, J.; Chi, C. Y.; Wu, J. S.. Chem. Eur. J., 2009, 15, 6050.
- 12b Yin, J.; Chi, C. Y.; Wu, J. S.. Org. Biomol. Chem., 2010, 8, 2594.
- 13 Wang, S. L.; Wang, Y. L.; Chen, Z. X.; Lin, Y. J.; Weng, L. H.; Han, K.; Li, J.; Jia, X. S.; Li, C. J.. Chem. Commun., 2015, DOI: 10.1039/c0XX00000x.