Abstract
A new tripodal rhodamine B derivative 2 was designed and synthesized by tripodal trialdehyde and rhodamine B hydrazide for the first time. This derivative could be used as a fluorescent chemosensor for the selective and sensitive determination of copper(II) in Tris-HCl buffer and ethanol aqueous mixed media. Under the optimum conditions described herein, fluorescence enhancement at 557/577 nm was linearly related to the concentration of copper(II) in the range of 0.10 to 10.00×10−5 mol·L−1, with a correlation coefficient of R 2=0.9964 (n=15) and a detection limit of 1.129×10−7 mol·L−1 (the relative standard deviation for five repeated measurements at 4.00×10−5 mol·L−1 Cu(II) was 2.2%). The absorbance measurements at 557 nm were linearly related to the concentration of Cu(II) in the range of 0.50 to 25.00×10−5 mol·L−1, with a correlation coefficient of R 2=0.9948 (n=13) and a detection limit of 3.338×10−7mol·L−1.
Similar content being viewed by others
References
Fu X, Rinaldo P, Hahn S H, Kodama H, Packman S. Mutation analysis of copper transporter genes in patients with ethylmalonic encephalopathy, mitochondriopathies and copper deficiency phenotypes. J Inherit Metab Dis, 2003, 26: 55–66
Lee M H, Kim H J, Yoon S, Park N, Kim J S. Metal ion induced FRET OFF-ON in tren/dansyl-appended rhodamine. Org Lett, 2008, 10(2): 213–216
Weng Y Q, Fan Y, Zhong Y R, Ye B H. A copper(II) ion-selective ON-OFF type fluoroionophore based on zinc porphyrin-dipyridylamino. Inorg Chem, 2007, 46(19): 7749–7755
Wen Z C, Yang R, He H, Jiang Y B. A highly selective charge transfer fluoroionophore for Cu2+. Chem Commun, 2006, 106–108
Jun E J, Won H N, Kim J S, Lee K H, Yoon J. Unique blue shift due to the formation of static pyrene excimer: Highly selective fluorescent chemosensor for Cu2+. Tetrahedron Lett, 2006, 47(27): 4577–4580
Maksim R, Dai Z H, James W C. Ratiometric displacement approach to Cu(?) sensing by fluorescence. J Am Chem Soc, 2005, 127(6): 1612–1613
Qi X, Jun E J, Xu L, Kim S J, Hong J S J, Yoon Y J, Yoon J. New BODIPY derivatives as OFF-ON fluorescent chemosensor and fluorescent chemodosimeter for Cu2+: Cooperative selectivity enhancement toward Cu2+. J Org Chem, 2006, 71(7): 2881–2884
Desvergne J P, Czarnik A W. Chemosensors of Ion and Molecule Recognition. Dordrecht, Netherlands: Kluwer Academic Publishers, 1997
Amendola V, Fabbrizzi L, Forti F, Licchelli M, Mangano C, Pallavicini P, Poggi A, Sacchi D, Taglieti A. Light-emitting molecular devices based on transition metals. Coord Chem Rev, 2006, 250: 273–299
Valeur B. Molecular Fluorescence: Principles and Applications. New York: Wiley-VCH Verlag GmbH, 2001. Chapter 10
Kwon J Y, Jang Y J, Lee Y J, Kim K M, Seo M S, Nam W, Yoon J. A highly selective fluorescent chemosensor for Pb2+. J Am Chem Soc, 2005, 127(28): 10107–10111
Lee M H, Wu J S, Lee J W, Jung J H, Kim J S. Highly sensitive and selective chemosensor for Hg2+ based on the rhodamine fluorophore. Org Lett, 2007, 9(13): 2501–2504
Wu J S, Hwang I C, Kim K S, Kim J S. Rhodamine-based Hg2+-selective chemodosimeter in aqueous solution: Fluorescent OFF-ON. Org Lett, 2007, 9(5): 907–910
Mao J, Wang L N, Dou W, Tang X L, Yan Y, Liu W S. Tuning the selectivity of two chemosensors to Fe(III) and Cr(III). Org Lett, 2007, 9(22): 4567–4570
Soh J H, Kim K S, Kim S K, Kim S, Lee S H, Yoon J. Rhodamine urea derivatives as fluorescent chemosensors for Hg2+. Tetrahedron Lett, 2007, 48(34): 5966–5969
Ammann D, Pretsch E, Simon W. A sodium ion-selective electrode based on a neutral carrier. Anal Lett, 1974, 7(1): 23–32
Jones M B, MacBeth C E. Tripodal phenylamine-based ligands and their Co complexes. Inorg Chem, 2007, 46(20): 8117–8119
Narinder S, Doo O J. Benzimidazole-based tripodal receptor: Highly selective fluorescent chemosensor for iodide in aqueous solution. Org Lett, 2007, 9(10): 1991–1994
Hu X L, Ingrid C R, Karsten M. Dioxygen activation by a low-valent cobalt complex employing a flexible tripodal N-heterocyclic carbene ligand. J Am Chem Soc, 2004, 126(41): 13464–13473
Kim J, Ryu D, Sei Y, Yamaguchib K, Ahn K H. Tripodal oxazoline-based homochiral coordination cages with internal binding sites. Chem Commun. 2006, 1136–1138
Dillip K C, Kaliappa G R, Thomas C W M, Parimal K B. Tetrahedral recognition of a water molecule by heteroditopic cryptands: X-ray structural studies. J Org Chem, 1996, 61(3): 1169–1171
Virginie D, Francis F, Anthony W C. A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water. J Am Chem Soc, 1997, 119(31): 7386–7387
Yang X F, Guo X Q, Zhao Y B. Development of a novel rhodamine-type fluorescent probe to determine peroxynitrite. Talanta, 2002, 57(5): 883-890
Yang X, Pan Z T, Ma Y. Rhodamine B as standard substance to measure the fluorescence-quantum yield of dichlorofluorescein. J Anal Sci (in Chinese), 2003, 19(6):: 588–589
Author information
Authors and Affiliations
Corresponding author
Additional information
Supported by the Foundation of the Governor of Guizhou Province, China (Grant No. 200617) and the Talented Person Foundation of Guizhou University (Grant No. 2007039)
Rights and permissions
About this article
Cite this article
Zeng, X., Wu, C., Dong, L. et al. A new tripodal rhodamine B derivative as a highly selective and sensitive fluorescence chemosensor for copper(II). Sci. China Ser. B-Chem. 52, 523–528 (2009). https://doi.org/10.1007/s11426-009-0098-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-009-0098-8