Coumarin Modified Rhodamine Derivative：Fluorescent Chemosensor Selectively Recognizing Al3+ and Ca2+

doi:10.1007/s40242-014-4008-z

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (3): 362-367.doi: 10.1007/s40242-014-4008-z

Previous Articles Next Articles

Coumarin Modified Rhodamine Derivative：Fluorescent Chemosensor Selectively Recognizing Al³⁺ and Ca²⁺

CAO Li, JIA Chunman, ZHANG Qi, CHEN Da, ZHANG Chunyan, QIAN Yaao

Hainan Provincial Key Lab of Fine Chem., Key Study Center for Tropical Resources Utilization, Ministry of Education, Hainan University, Haikou 570228, P. R. China

Received:2014-01-06 Revised:2014-02-20 Online:2014-06-01 Published:2014-03-05
Contact: ZHANG Qi E-mail:hnfinechem@163.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21261008), the Key Scientific and Technological Plan Project of Hainan Province, China(No.ZDXM20110024), the Hainan Province Special Integration Fund of Industry and Research, China(No.CXY20130010) and the International Science and Technology Cooperation Projects of Hainan Province, China(No. KJHZ2014-05).

Abstract

Abstract:

A fluorescent probe with a coumarin moiety bound to rhodamine 6G hydrazide(1) was synthesized. Its sensing behavior toward various metal ions was investigated with fluorescence methods. Compound 1 displays different fluorescence emission responses to Al³⁺and Ca²⁺ at the same excitation wavelength in the visible light region, while no changes occur after the addition of other metal ions. The binding ratios of the complexs of 1-Al³⁺ and 1-Ca²⁺are both 2:1 according to the Job plot and high resolution mass spectrometer(HRMS) experiments. Moreover, emission spectrum of 1-Ca²⁺ complex and absorption spectrum of the rhodamine dyes overlap largely. When Al³⁺ was added to the 1-Ca²⁺system, calcium in complex 1-Ca²⁺ can be displaced by Al³⁺, resulting in the output of another ratiometric sensing signal, which demonstrates that the 1-Ca²⁺ complex can be served as a new and effective fluorescence resonance energy transfer(FRET) donor for rhodamine derivatives.

Key words: Chemosensor, Aluminium ion, Calcium ion, Fluorescence resonance energy transfer(FRET)

CAO Li, JIA Chunman, ZHANG Qi, CHEN Da, ZHANG Chunyan, QIAN Yaao. Coumarin Modified Rhodamine Derivative：Fluorescent Chemosensor Selectively Recognizing Al³⁺ and Ca²⁺[J]. Chemical Research in Chinese Universities, 2014, 30(3): 362-367.

References

[1] Zhang J. F., Zhou Y., Yoon J. Y., Kim S. J., Kim J. S., Org. Lett., 2010, 12, 3852
[2] Lei Z. J., Zhang C. Z., Hu Q. H., Liu Y., Zhang Q., Liu X. J., Chin. J. Anal. Chem., 2012, 40, 1827
[3] Robinson G. H., Chem. Eng. News, 2003, 81, 54
[4] Altschuler E., Med. Hypotheses, 1999, 53, 22
[5] Wang B., Xing W., Zhao Y., Deng X., Environ. Toxicol. Phar., 2010, 29, 308
[6] Walton J. R., Neurotoxicology, 2006, 27, 385
[7] Polizzi S., Neurotoxicology, 2002, 23, 761
[8] Hahn S. H., Tanner M. S., Danke D. M., Gahl W. A., Biochem. Mol. Med., 1995, 54, 142
[9] Berridge M. J., Nature, 1993, 361, 315
[10] Strieker S. A., Centonze V. E., Paddock S. W., Schattenet G., Dev. Biol., 1992, 149, 370
[11] Whitaker M., Patel R., Development, 1990, 108, 525
[12] Clapham D. E., Cell, 1995, 80, 259
[13] Carafoli E., Proc. Natl. Acad. Sci., 2002, 99, 1115
[14] Kim S. H., Choi H. S., Kim J., Lee S. J., Quang D. T., Kim J. S., Org. Lett., 2010, 12, 560
[15] DeSilva A. P., Gunaratne H. Q. N., Gunnlaugsson T., Huxley A. J. M., McCoy C. P., Rademacher J. T., Rice T. E., Chem. Rev., 1997, 97, 1515
[16] Wang L. N., Qin W. W., Tang X. L., Dou W., Liu W. S., Teng Q. F., Yao X. J., Org. Biomol. Chem., 2010, 8, 3751
[17] Gou C., Qin S. H., Wu H. Q., Wang Y., Luo J., Liu X. Y., Inorg. Chem. Commun., 2011, 14, 1622
[18] Kim J., Morozumi T., Nakamura H., Org. Lett., 2007, 9, 4419
[19] Emrullahoglu M., Karakus E., Ucuncu M., Chem. Commun., 2013, 49, 7836
[20] Zhou X., Yan W., Zhao T., Tian Z. X., Wu X., Tetrahedron, 2013, 69, 9535
[21] Neupane L. N., Park J. Y., Park J. H., Lee K. H., Org. Lett., 2013, 15, 254
[22] Liu S. K., Zhou C. Y., Du J. H., Gao J. G., Zhou J., Chin. J. Anal. Chem., 2013, 41, 732
[23] Kim H. N., Lee M. H., Kim H. J., Kim J. S., Yoon J., Chem. Soc. Rev., 2008, 37, 1465
[24] Mao J., Wang L. N., Dou W., Tang X. L., Yan Y., Liu W. S., Org. Lett., 2007, 9, 4567
[25] Suzuki Y., Komatsu H., Iked T., Saito N., Araki S., Citterio D., Hisamoto H., Kitamura Y., Kubota T., Nakagawa J., Oka K., Suzuki K., Anal. Chem., 2002, 74, 1423
[26] Lin W. Y., Yuan L., Feng J. B., Eur. J. Org. Chem., 2008, 16, 3821
[27] Yuan L., Lin W. Y., Chen B., Xie Y. N., Org. Lett., 2012, 14, 432
[28] An J. M., Yang Z. J., Yan M. H., Li T. R., J. Lumin., 2013, 139, 79
[29] Ma Q. J., Zhang X. B., Zhao X. H., Jin Z., Mao G. J., Shen G. L., Yu R. Q., Anal. Chim. Acta, 2010, 663, 85
[30] Liu W. Y., Li H. Y., Lü H. S., Zhao B. X., Miao J. Y., Spectrochim. Acta Part A, 2012, 95, 658
[31] Goswamia S., Sena D., Dasa A. K., Dasa N. K., Sens. Actuators B, 2013, 183, 518
[32] Lee K. S., Kim H. J., Kim G. H., Shin I., Hong J. I., Org. Lett., 2008, 10, 49
[33] Cao B. N., Hu Q., Huang Y., Jia C. M., Zhang Q., Chem. Res. Chinese Universities, 2013, 29(3), 419
[34] Yuan L., Lin W. Y., Yang Y. T., Song J. Z., Chem. Commun., 2011, 47, 4703
[35] Martin R. B., Acc. Chem. Res., 1994, 27, 204
[36] Yang X. F., Zhao M. L., Wang G., Sens. Actuators B, 2011, 152, 8

Coumarin Modified Rhodamine Derivative：Fluorescent Chemosensor Selectively Recognizing Al³⁺ and Ca²⁺

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	LI Mingfeng, FANG Hongbao, JI Yifan, CHEN Yuncong, HE Weijiang, GUO Zijian. Rational Design of Ratiometric Fe³⁺ Fluorescent Probes Based on FRET Mechanism [J]. Chemical Research in Chinese Universities, 2022, 38(1): 67-74.
[2]	FETTOUCHE Souad, BOUKHRISS Aicha, TAHIRI Mohamed, CHERKAOUI Omar, BAZI Fathallaah, GMOUH Said. Naked Eye and Selective Detection of Copper(Ⅱ) in Mixed Aqueous Media Using a Cellulose-based Support [J]. Chemical Research in Chinese Universities, 2019, 35(4): 598-603.
[3]	FENG Jia, SHAO Xiuqing, SHANG Zhuobin, CHAO Jianbin, WANG Yu, JIN Weijun. A New Biphenylcarbonitrile Based Fluorescent Sensor for Zn²⁺ Ions and Application in Living Cells [J]. Chemical Research in Chinese Universities, 2017, 33(5): 695-701.
[4]	JI Yanyan, ZHANG Bing, ZHANG Wu, ZHAO Bo, LI Hongbo, WANG Dongmei, LI Ying. High-efficient Synthesis of Zeolite LTA via a Wet-gel Crystallization Route [J]. Chemical Research in Chinese Universities, 2017, 33(4): 520-524.
[5]	SU Jie, HUANG Shanshan, HE Song, ZENG Xianshun. Sensitive and Selective Fluorescent Chemosensors Combining Multiple PET Processes for Ag⁺ Sensing [J]. Chemical Research in Chinese Universities, 2016, 32(1): 20-27.
[6]	LIANG Fanghui, WANG Di, MA Pinyi, WANG Xinghua, SONG Daqian, YU Yong. A Highly Selective and Sensitive Ratiometric Fluorescent Probe for pH Measurement Based on Fluorescence Resonance Energy Transfer [J]. Chemical Research in Chinese Universities, 2015, 31(5): 724-729.
[7]	YANG Huixiao, HU Qinzhi, MA Guochun, CHEN Guofeng, TAO Minli, ZHANG Wenqin. Hg²⁺-Selective Fluorescent Chemosensor Based on Cation-π Interaction [J]. Chemical Research in Chinese Universities, 2014, 30(6): 910-914.
[8]	TANG Duihai, ZHANG Weiran, WANG Yifan, MIAO Jing, QIAO Zhen'an, HUO Qisheng, ZHANG Lirong. co-Condensation Synthesis of Salicylaldimine Calcium Complex Containing Mesoporous Silica Nanoparticles as Carriers for Drug Release [J]. Chemical Research in Chinese Universities, 2014, 30(4): 531-537.
[9]	QIN Penghua, LÜ Wencai, QIN Wei, ZHANG Wei, XIE Hui. Theoretical Studies on Complexes of Calcium Ion with Amino Acids [J]. Chemical Research in Chinese Universities, 2014, 30(1): 125-129.
[10]	HE Song, LIU Qiuchen, LI Yuanyuan, WEI Fangfang, CAI Songtao, LU Yan, ZENG Xianshun. Rhodamine 6G-based Chemosensor for the Visual Detection of Cu²⁺ and Fluorescent Detection of Hg²⁺ in Water [J]. Chemical Research in Chinese Universities, 2014, 30(1): 32-36.
[11]	CHENG Peng-fei, XU Kuo-xi, YAO Wen-yong, KONG Hua-jie, KOU Li, MA Xiao-dan, WANG Chao-jie. Novel Fluorescent Chemosensors Based on Tryptophan Unit for Cu²⁺ and Fe³⁺ in Aqueous Solution [J]. Chemical Research in Chinese Universities, 2013, 29(4): 642-646.
[12]	SU Wen-qi, YANG Bing-qin. Novel Highly Selective Fluorescent Chemosensors for Hg(II) [J]. Chemical Research in Chinese Universities, 2013, 29(4): 657-662.
[13]	CAO Ben-nan, HU Qin, HUANG Yan, JIA Chun-man, ZHANG Qi. Highly Sensitive and Selective Chemosensor for Cu²⁺ Based on a Schiff Base [J]. Chemical Research in Chinese Universities, 2013, 29(3): 419-423.
[14]	WANG Xiu-li*, ZHENG Wen-yan, LIN Hong-yan and LIU Guo-cheng. Phenanthroline-based Fluorescent Chemosensor for Selective Detection of Zn2+ in DMF Buffer Solution [J]. Chemical Research in Chinese Universities, 2010, 26(6): 884-887.
[15]	FAN Cai-ling, DAI Xing, YANG Wu-min, WANG Xing-feng and YANG Yun-xu. A Quinoline Derivated Chemosensor for Cu²⁺ Recognition [J]. Chemical Research in Chinese Universities, 2009, 25(5): 620-623.