Abstract
Five rare earth-indole carboxylic acid complexes: [Eu(IAA)2(phen)2]·NO3 (1) (IAA = indole acetic acid, phen = o-phenanthroline); [Nd(IAA)2(phen)2]·NO3 (2); [Er(IBA)3(phen)](phen)·HNO3·H2O (3) (IBA = indole butyric acid); [Ce(IBA)3(phen)](phen)·HNO3·H2O (4); [Dy(IBA)3(phen)](phen)·HNO3·H2O (5) were synthesized and characterized. Then, we reported their properties as dye adsorption and fluorescence sensing for the first time. The fluorescence explorations demonstrated that complex 1 exhibits highly selective and sensitive sensing for nitro aromatic compounds with high sensitivity (1.49 × 107 M−1) and low detection limit (11.40 µM). Meanwhile, these complexes also exhibit stronger selective adsorption of dye molecules (MB and MG) in aqueous solution. This study provides new physical insights into the rational design of lanthanide complexes based on multifunctional materials.
Graphical Abstract
We firstly reported five lanthanide complexes and displayed fluorescence sensing and selective adsorption dye properties.
Similar content being viewed by others
References
H.F. Higginbotham, R.P. Cox, S. Sandanayake, B.A. Graystone, S.J. Langford, T.D.M. Bell, Chem. Commun. 49, 5061 (2013)
M.I.J. Stich, L.H. Fischer, O.S. Wolfbeis, Chem. Soc. Rev. 39, 3102 (2010)
S.K. Sahoo, G.D. Kim, H.J. Choi, J. Photochem. Photobiol. C 27, 30 (2016)
S.K. Sahoo, D. Sharma, R.K. Bera, G. Crisponi, J.F. Callan, Chem. Soc. Rev. 41, 7195 (2012)
J. Wang, A. Groeneveld, M. Oikonomou, A. Prusova, A.H. Van, J.W. van Lent, Soft Matter 12, 99 (2015)
Y.Z. Ye, S. Lin, X.J. Wu, Struct. Chem. 33, 1649 (2014)
Y. Sun, L. Wang, W.A. Amer, H. Yu, J. Ji, L. Huang et al., J Inorg Organomet. Polym. Mater. 23, 270 (2013)
T.A. Makal, J.R. Li, W. Lu, H.C. Zhou, Chem. Soc. Rev. 41, 7761 (2012)
J. Yang, J. Mater. Chem. 30, 3154 (2012)
H.R. Kim, T.U. Yoon, S.I. Kim, J. An, Y.S. Bae, Y.L. Chang, RSC Adv. 7, 1266 (2017)
H. Wu, Q. Gong, D.H. Olson, J. Li, Chem. Rev. 112, 836 (2012)
Z. Zhang, Y. Zhao, Q. Gong, Z. Li, J. Li, Chem. Commun. 49, 653 (2013)
P. Nugent, Y. Belmabkhout, S.D. Burd, A.J. Cairns, R. Luebke, K. Forrest, Nature 495, 80 (2013)
M. Andruh, J.P. Costes, C. Diaz, S. Gao, Inorg. Chem. 40, 3342 (2009)
L.F. Zou, L. Zhao, Y.N. Guo, G.M. Yu, Y. Guo, J. Tang et al., Chem. Commun. 47, 8659 (2001)
Y.Z. Zheng, M. Evangelisti, F. Tuna, R.E. Winpenny, J. Am. Chem. Soc. 134, 1057 (2012)
J.Y. Lee, O.K. Farha, J. Roberts, K.A. Scheidt, S.B.T. Nguyen, J.T. Hupp, Chem. Soc. Rev. 38, 1450 (2009)
L. Ma, C. Abney, W. Lin, ChemInform 40, 33 (2009)
M. Yoon, R. Srirambalaji, K. Kim, Chem. Rev. 112, 1196 (2012)
J. Zhang, A.V. Biradar, S. Pramanik, T.J. Emge, T. Asefa, J. Li, Chem. Commun. 43, 6541 (2012)
H.R. Moon, D.W. Lim, M.P. Suh, Chem. Soc. Rev. 42, 1807 (2013)
Y. Li, A. Pang, C. Wang, M. Wei, J. Mater. Chem. 21, 17259 (2011)
G.K.H. Shimizu, J.M. Taylor, S.R. Kim, Science 341, 354 (2013)
X. Shen, B. Yan, Chem. Soc. Rev. 45, 1273 (2016)
J.B. Decoste, G.W. Peterson, Chem. Rev. 114, 5695 (2014)
O. Pinrat, K. Boonkitpatarakul, W. Paisuwan, M. Sukwattanasinitt, A. Ajavakom, The Analyst 140, 1886–1893 (2015)
P. Mahata, D.K. Singha, RSC Adv. 5, 28092 (2015)
N. Dey, S.K. Samanta, S. Bhattacharya, Appl. Mater. Interfaces 5, 8394 (2013)
X.G. Li, Y. Liao, M.R. Huang, V. Strong, R.B. Kaner, Chem. Sci. 4, 1970 (2013)
J. Yan, J.C. Ni, J.X. Zhao, L.X. Sun, F.Y. Bai, Z. Shi, Tetrahedron 1145, 5 (2017)
L. Lin, M. Rong, S. Lu, X. Song, Y. Zhong, J. Yan, Nanoscale 7, 1872 (2015)
F. Zhang, L. Luo, Y. Sun, F. Miao, J. Bi, S. Tan, Tetrahedron 46, 69 (2013)
T. Devic, C. Serre, N. Audebrand, J. Marrot, G. Férey, J. Am. Chem. Soc. 127, 12788 (2005)
R.S. Zhou, X.B. Cui, J.F. Song, X.Y. Xu, J. Solid State Chem. 181, 2099 (2008)
D.R. Xiao, J.H. He, D.Z. Sun, H.Y. Chen, S.W. Yan, X. Wang, Eur. J. Inorg. Chem. 11, 2012 (2012)
X. Guo, G. Zhu, Z. Li, F. Sun, Z. Yang, S. Qiu, Chem. Commun. 30, 3172 (2006)
B. Chen, Y. Yang, F. Zapata, G. Lin, G. Qian, E. Lobkovsky, Adv. Mater. 19, 1693 (2010)
F.N. Shi, L. Cunha-Silva, R.A. Ferreira, L. Mafra, T. Trindade, L.D. Carlos, J. Am. Chem. Soc. 130, 150 (2008)
B.M. Baron, R.J. Cregge, R.A. Farr, D. Friedrich, R.S. Gross, B.L. Harrison, J. Med. Chem. 48, 995 (2005)
P. Kutschy, M. Dzurilla, M. Takasugi, A. Sabová, Collect. Czech. Chem. Commun. 64, 348 (1999)
E. Tsavkelova, B. Oeser, L. Oren-Young, M. Israeli, Y. Sasson, B. Tudzynski et al., Fungal Genet. Biol. 49, 48 (2012)
A.S. Gurkan-Alpa, C.A. Andac, E. Dayanc, R. Cetin-Atalay, E. Buyukbingol, Eur. J. Med. Chem. 12, 58 (2012)
L.F.F. Dalmazzo, B.A. Santana-Lemos, R.H. Jácomo, A.B. Garcia, E.M. Rego, L.M.D. Fonseca et al., Leuk. Res. 35, 657 (2011)
S. Lata, B. Batra, C.S. Pundir, Process Biochem. 47, 2131 (2012)
Y. Sun, L. Wang, W.A. Amer, H. Yu, J. Ji, L. Huang, J. Inorg. Organomet. Polym. Mater. 23, 270 (2013)
T. Suzuki, H. Ohshima, Chem. Res. Toxicol. 3, 16 (2003)
Q.L. Guan, Y.H. Xing, J. Liu, W.J. Wei, R. Zhang, X. Wang, J. Inorg. Biochem. 128, 57 (2013)
Q. Zhou, T.W. Hambley, B.J. Kennedy, P.A. Lay, Inorg. Chem. 42, 8557 (2003)
J.E. Weder, C.T. Dillon, T.W. Hambley, B.J. Kennedy, P.A. Lay, J.R. Biffin, Coord. Chem. Rev. 232, 95 (2002)
R.M. Ying, P. Turner, B.J. Kennedy, T.W. Hambley, P.A. Lay, J.R. Biffin, Inorg. Chim. Acta 324, 150 (2001)
Z.N. Wang, X.T. Xu, X. Lv, F.Y. Bai, S.Q. Liu, Y.H. Xing, RSC Adv. 5, 104263 (2015)
N. Du, X. Gao, J. Song, Z.N. Wang, Y.H. Xing, F.Y. Bai, RSC Adv. 6, 75 (2016)
N. Du, J. Song, S. Li, Y.X. Chi, F.Y. Bai, Y.H. Xing, ACS Appl. Mater. Interfaces 8, 42 (2016)
B. Gole, W. Song, M. Lackinger, P.S. Mukherjee, Chemistry 20, 13662 (2014)
X. Gao, C. Wang, Z.F. Shi, J. Song, F.Y. Bai, J.X. Wang et al., Dalton Trans. 44, 11562 (2015)
Acknowledgements
This work was supported by the Grants of the National Natural Science Foundation of China (Nos. 21571091, 21371086) and Commonweal Research Foundation of Liaoning province in China (No. 20170055).
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Liu, C.H., Zhang, L.J., Bai, F.Y. et al. Dye Adsorption and Fluorescence Sensing Behaviour About Rare Earth-Indole Carboxylic Acid Complexes. J Inorg Organomet Polym 28, 1839–1849 (2018). https://doi.org/10.1007/s10904-018-0869-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10904-018-0869-9