New ferrocenyl derivative with controllable aggregation-induced
emission (AIE) characteristics

doi:10.1007/s11458-010-0110-z

Front. Chem. China

2010, Vol. 5

Issue (2) : 241-246 https://doi.org/10.1007/s11458-010-0110-z

Research articles

New ferrocenyl derivative with controllable aggregation-induced emission (AIE) characteristics

Dong ZHANG,Liangliang ZHU,Hong LI,Jianhua SU,

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China;

Download: PDF(273 KB)
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract A novel molecular switch, 7-(N,N-diethylamino)-2-oxo-2H-chromen-4-yl ferrocene carboxylate (FCC), was synthesized and fully characterized by ¹H NMR, ¹³C NMR, and HRMS. Taking advantage of the properties of ferrocene as an electron donor active unit and the coumarin as a fluorescent unit, the dyad FCC shows a fast and reversible redox-switchable fluorescence emission. In sharp contrast to most photoluminescent chromophores, FCC has a unique enhanced emission through aggregation. The change of electrochemical signals (CV and DPV) indicated that the ferrocene (F_c) unit of FCC could form inclusion complex with Me-b-cyclodextrin (CD). This inclusion complex could further weaken the aggregation-induced emission (AIE) effect remarkably. This advance paves the way to introduce AIE property into molecular devices applications.

Keywords ferrocene cyclodextrin molecular switch fluorescence aggregation-induced emission (AIE)

Issue Date: 05 June 2010

Cite this article:

Dong ZHANG,Hong LI,Liangliang ZHU, et al. New ferrocenyl derivative with controllable aggregation-induced emission (AIE) characteristics[J]. Front. Chem. China, 2010, 5(2): 241-246.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-010-0110-z
https://academic.hep.com.cn/fcc/EN/Y2010/V5/I2/241

	Zhang, H.; Wang, Q.; Liu, M.; Ma, X.; Tian, H., Org. Lett. 2009, 11, 3234―3237 doi: 10.1021/ol9011794
	Ma, X.; Tian, H., Chem. Soc. Rev. 2009, 39, 70―80 doi: 10.1039/b901710k
	Balzani, V., Molecular Devices and Machines: A Journeyinto the Nano World; Wiley-VCH: Weinheim, Germany, 2003 doi: 10.1002/3527601600
	Badjic, J. D.; Balzani, V.; Credi, A.; Silvi, S.; Stoddart, J. F., Science2004, 303, 1845―1849 doi: 10.1126/science.1094791
	Zhou, Y. C.; Wu, H.; Qu, L.; Zhang, D. Q.; Zhu, D. B., J. Phys. Chem. B2006, 110, 15676―15679 doi: 10.1021/jp062849t
	de Silva, A. P.; Uchiyama, S., Nat. Nanotechnol. 2007, 2, 399―410 doi: 10.1038/nnano.2007.188
	Kou, S.; Lee, H. N.; van Noort, D.; Swamy, K. M. K.; Kim, S. H.; Soh, J. H.; Lee, K. M.; Nam, S. W.; et al, Angew. Chem. Int. Ed. 2008, 47, 872―876 doi: 10.1002/anie.200703813
	Amendola, V.; Dallacosta, C.; Fabbrizzi, L.; Monzani, E., Tetrahedron2008, 64, 8318―8323 doi: 10.1016/j.tet.2008.05.041
	Feringa, B. L., Molecular Switches; Wiley-VCH: Weinheim,Germany, 2001 doi: 10.1002/3527600329
	Martínez, R.; Ratera, I.; Tárraga, A.; Molina, P.; Veciana, J., Chem. Commun. 2006, 36, 3809―3811 doi: 10.1039/b608264e
	Zhang, R.; Wang, Z.; Wu, Y.; Fu, H.; Yao, J., Org. Lett. 2008, 10, 3065―3068 doi: 10.1021/ol801053t
	Zhao, Q.; Li, L.; Li, F.; Yu, M.; Liu, Z.; Yi, T.; Huang, C., Chem. Commun. 2008, 6, 685―687 doi: 10.1039/b712416c
	Lim, S. J.; An, B. K.; Jung, S. D.; Chung, M. A.; Park, S. Y., Angew. Chem. Int. Ed. 2004, 43, 6346―6350 doi: 10.1002/anie.200461172
	Zeng, Q.; Li, Z.; Dong, Y.; Di, C.; Qin, A.; Hong, Y.; Ji, L.; Zhu, Z.; et al, Chem. Commun. 2006, 1, 70―72
	Huang, J.; Wang, M.; Zhou, Y.; Weng, X.; Shuai, L.; Zhou, X.; Zhang, D., Bioorg. Med. Chem. 2009, 17, 7743―7748 doi: 10.1016/j.bmc.2009.09.040
	Zheng, Y. S.; Hu, Y. J., J. Org. Chem. 2009, 74, 5660―5663 doi: 10.1021/jo900527e
	Lim, S. J.; An, B. K.; Jung, S. D.; Chung, M. A.; Park, S. Y., Angew. Chem. Int. Ed. 2004, 43, 6346―6350 doi: 10.1002/anie.200461172
	Liu, Y.; Tao, X.; Wang, F.; Dang, X.; Zou, D.; Ren, Y.; Jiang, M., J. Phys. Chem. C2008, 112, 3975―3981 doi: 10.1021/jp7117373
	Yang, Z.; Chi, Z.; Yu, T.; Zhang, X.; Chen, M.; Xu, B.; Liu, S.; Zhang, Y.; Xu, J., J. Mater. Chem. 2009, 19, 5541 doi: 10.1039/b902802a
	Kaifer, A. E., Acc. Chem. Res. 1999, 32, 62―71 doi: 10.1021/ar970335u
	Jabin, I.; Revial, G.; Monnier-Benoit, N.; Netchitaïlo, P., J. Org. Chem. 2001, 66, 256―261 doi: 10.1021/jo005657h
	Chen, Y. S.; Kuo, P. Y.; Shie, T. L.; Yang, D. Y., Tetrahedron2006, 62, 9410―9416 doi: 10.1016/j.tet.2006.07.053
	Kang, L.; Wang, Z.; Cao, Z.; Ma, Y.; Fu, H.; Yao, J., J. Am. Chem. Soc. 2007, 129, 7305―7312 doi: 10.1021/ja068710d
	Ning, Z.; Chen, Z.; Zhang, Q.; Yan, Y.; Qian, S. X.; Cao, Y.; Tian, H., Adv. Funct. Mater. 2007, 17, 3799―3807 doi: 10.1002/adfm.200700649
	Hong, Y.; Lam, J. W. Y.; Tang, B. Z., Chem. Commun. 2009, 29, 4332―4353 doi: 10.1039/b904665h
	Zhang, D.; Zhang, Q.; Su, J.; Tian, H., Chem. Commun. 2009, 13, 1700―1702 doi: 10.1039/b823073k
	Dawson, W. R.; Windsor, M. W., J. Phys. Chem. 1968, 72, 3251―3260 doi: 10.1021/j100855a027
	Szejtli, J., Chem. Rev. 1998, 98, 1743―1754 doi: 10.1021/cr970022c
	Hapiot, F.; Tilloy, S.; Monflier, E., Chem. Rev. 2006, 106, 767―781 doi: 10.1021/cr050576c
	Buriez, O.; Heldt, J. M.; Labbé, E.; Vessières, A.; Jaouen, G.; Amatore, C., Chemistry2008, 14, 8195―8203 doi: 10.1002/chem.200800507
	These literatures describe the association constants(Kass) between β-CD and coumarin: a) Scypinski S. and Drake J. M., J. Phys. Chem. 1985, 89, 2432―2435; b) Takakusa H., Kikuchi K., Urano Y., Higuchi T., and Nagano T., Anal. Chem. 2001, 73, 939―942

[1]	Mingzhu LI, Yanlin SONG, . High effective sensors based on photonic crystals[J]. Front. Chem. China, 2010, 5(2): 115-122.
[2]	Bo LIU, Duo FAN, Qiong ZHANG, Yu CHEN, Weihong ZHU, . A novel NIR violanthrone derivative with high electron-deficiency: effect of fluorescence on dicyanomethylene substitution[J]. Front. Chem. China, 2010, 5(2): 200-207.
[3]	Yi-Bin RUAN, Stephane MAISONNEUVE, Juan XIE, Chun LI, Jie TANG, . Cooperative recognition of Cu 2+ based on amino acids tethered benzothiadiazoyl-bistriazoles[J]. Front. Chem. China, 2010, 5(2): 208-213.
[4]	Qingxian LIAO, Aifang LI, Zhao LI, Yibin RUAN, Yunbao JIANG, . A novel intramolecular charge transfer fluorescent chemosensor highly selective for Cu 2+ in neutral aqueous solutions[J]. Front. Chem. China, 2010, 5(2): 178-183.
[5]	Quanguo WANG, Yubin DING, Weihong ZHU, Yongshu XIE, . A novel fluorescence enhancing F - probe based on intermolecular energy transfer[J]. Front. Chem. China, 2010, 5(2): 162-165.
[6]	Wenguo XING, Yunhe WEI, Ping YU, Changqiao ZHANG, Jian LI, . 6-O-(2-hydroxybutyl)-β-CD as a chiral selector for nonaqueous capillary electrophoretic separation of chiral drugs[J]. Front. Chem. China, 2009, 4(4): 396-401.
[7]	Liangzhun YANG, Lanfen ZHANG, Jun CHEN, Liwen REN, Yanting ZHU, Xiuying WANG, Xibin YU. Study on the fluorescence and thermal stability of hybrid materials Eu(Phen)₂Cl₃/MCM-41[J]. Front Chem Chin, 2009, 4(2): 149-153.
[8]	Chao XIE, Chaoqing DONG, Jicun REN. Fluorescence cross-correlation spectroscopy using single wavelength laser[J]. Front Chem Chin, 2009, 4(2): 191-195.
[9]	Junzhen ZHANG, Bingqin YANG, Yating YANG, Binglin ZHANG. Synthesis, characterization and crystal structure of 1-ferrocenesulfonyl-2-long carbon chain alkyl benzimidazole[J]. Front Chem Chin, 2009, 4(1): 52-57.
[10]	OUYANG Xinhua, ZENG Heping, XIE Yan. Synthesis and photoluminescence properties of 8-hydroxyquinoline derivatives and their metallic complexes[J]. Front. Chem. China, 2007, 2(4): 407-413.
[11]	GONG Linbo, GONG Shuling, DONG Haiqing, ZHANG Chunlei, CHEN Yuanyin. Liquid crystalline behavior and fluorescent property of calix[4]arene containing azobenzene photochromic group[J]. Front. Chem. China, 2007, 2(3): 292-295.
[12]	YAN Jinhong, ZHANG Cuiping, YANG Pin. Study on inclusion complexes of hydroxypropyl-β-cyclodextrin with tanshinone IIA[J]. Front. Chem. China, 2007, 2(1): 50-54.
[13]	Tang Ruiren, Yan Zi′er, Luo Yiming, Guo Cancheng. Synthesis of Eu(Ⅲ) and Tb(Ⅲ) complexes with novel pyridine dicarboxylic acid derivatives and their fluorescence properties[J]. Front. Chem. China, 2006, 1(4): 408-413.
[14]	Tian Hongye, Shao Jun, He Rong, Gao Feng, Cui Daxiang, Gu Hongchen. Preparation and properties of polymer and quantum dot composites[J]. Front. Chem. China, 2006, 1(4): 474-478.
[15]	Jin Zhong, Liu Wei, Hu Yan, Liu Jianbing, Shao Ling, Fang Jianxin. Synthesis, structure and biological activity of 1-(1-methoxy-1-ferrocenyl-3-arylpropan-2-yl)-1H-1,2,4-triazole derivatives[J]. Front. Chem. China, 2006, 1(3): 287-291.

Viewed

Full text

Abstract

Cited

Shared

Discussed