Abstract
A monomer 1-acrolyl-2-rhodamine 6G hydrazide (AR6GH) was synthesized by the heterogeneous reaction of acryloyl chloride with rhodamine 6G hydrazide (R6GH) and characterized by 1H NMR, FTIR and elememtal analyses. Then it was micellar copolymerized with acrylamide (AM), acrylic acid (AA) to obtain a water-soluble fluorescent copolymers (poly(AM-AA-AR6GH)) which were characterized by the method of FTIR and 1H NMR. The viscosity average molecular weight M η – of poly(AM-AA) and poly(AM-AA-AR6GH)s were 1.76 × 106, 8.58 × 104 and 7.68 × 104 g/mol, respectively. The fluorescent characteristic of the aqueous solutions of copolymers was investigated both in varied pH and in the presence of metal cations. The poly(AM-AA-AR6GH) was found to be a selective chemosensor for Hg2+, Cd2+, Fe2+, Pb2+ ions. Obvious fluorescence enhancement was due to the photophysical response of the copolymer to the presence of Hg2+, Cd2+, Fe2+, or Pb2+ ions. In addition, the ability of the copolymer to detect different metal cations (Ag+, Ba2+, Co2+, Cd2+, Cr3+, Cu2+, Fe2+, Fe3+, Hg2+, K+, Mg2+, Mn2+, Na+, Ni2+, Pb2+, Zn2+) in aqueous solution was studied. The results suggest that copolymer may offer potential application for sensors of Hg2+, Cd2+, Fe2+, or Pb2+ ions in aqueous solution.
Similar content being viewed by others
References
Kim HN, Guo ZQ, Zhu WH, Yoon JY, Tian H (2011) Chem Soc Rev 40:79
Gunnlaugsson T, Glynn M, Tocci GM, Kruger PE, Pfeffer FM (2006) Coord Chem Rev 250:3094
Wang Y, Wu HQ, Luo J, Liu XY (2012) React Funct Polym 72:169
Beija M, Afonso CAM, Martinho JMG (2009) Chem Soc Rev 38:2410
Yang H, Zhou ZG, Huang KW, Yu MX, Li FY, Yi T, Huang CH (2007) Org Lett 9(23):4729
Huang W, Wu DY, Wu GH, Wang ZQ (2012) Dalton Trans 41:2620
Wu DY, Wang ZQ, Wu GH, Huang W (2012) Mater Chem Phys 137:428
Huang W, Wu DY, Duan CY (2010) Inorg Chem Commun 13:294
Wu GH, Wang DX, Wu DY, Gao Y, Wang ZQ (2009) J Chem Sci 121(4):543
Huang W, Zhu X, Wu DY, He C, Hu XY, Duan CY (2009) Dalton Trans 10457
Kaoutit HE, Estévez P, Ibeas S, García FC, Serna F, Benabdelouaha FB, García JM (2013) Dyes Pigments 96:414
Luo J, Jiang S, Qin S, Wu H, Wang Y, Jiang J et al (2011) Sens Actuators B: Chem 160:1191
Vallejos S, Estévez P, García FC, Serna F, Peña JL, García JM (2010) Chem Commun 46:7951
Vallejos S, El Kaoutit H, Estévez P, García FC, Serna F, Peña JL et al (2011) Polym Chem 2:1129
He F, Feng F, Wang S, Li Y, Zhu F (2007) J Mater Chem 17:3702
Feng X, Liu L, Wang S, Zhu D (2010) Chem Soc Rev 39:2411
Wang BY, Guan XL, Hu YL, Su ZX (2008) J Polym Res 15:427
Liu YH, Meng LZ, Lu XJ, Zhang LF, He YB (2008) Polym Adv Technol 19:137
Itaya T, Honda T, Kusumoto N, Matsumoto A, Inoue K (2003) Polym 44:2927
Kalogianni A, Pefkianakis E, Stefopoulos A, Bokias G, Kallitsis JK (2010) J Polym Sci B Polym Phys 48:2078
Shiraishi Y, Miyamoto R, Hira T (2008) J Photoch Photobio A 200:432
Tiera MJ, Oliveira VAD, Burrows HDM, Miguel DG, Neumann MG (1998) Colloid Polym Sci 276:206
Niamsa N, Kaewtong C, Srinonmuang W, Wanno B, Pulpokab B, Tuntulani T (2013) Polym Chem 4:3039
Hill A, Candau F, Selb J (1993) Macromol 26:4521
Geoffrey LS, McCormick CL (2001) Macromol 34:5579
Geoffrey LS, McCormick CL (2001) Macromol 34:918
Yang XF, Guo XQ, Zhao YB (2002) Talanta 57:883
Huang KW, Yang H, Zhou ZG et al (2008) Org Lett 10:2557
Virginie D, Francis F, Anthony WC (1997) J Am Chem Soc 119:7386
Gawdzik B, Kovtun O (2005) J Appl Polym Sci 98:2461
Kim KN, Choi MG, Noh JH, Ahn S, Chang SK (2008) Bull Korean Chem Soc 29(3):571
Zheng H, Qian ZH, Xu L, Yuan FF, Lan LD, Xu JG (2006) Org Lett 8(5):859
Shang GQ, Gao X, Chen MX, Zheng H, Xu JG (2008) J Fluoresc 18:1187
Yu MX, Shi M, Chen ZG, Li FY, Li XX, Gao YH, Xu J, Yang H, Zhou ZG, Yi T, Huang CH (2008) Chem Eur J 14(23):6892
Zhou ZG, Yu MX, Yang H, Huang KW, Li FY, Yi T, Huang CH (2008) Chem Comm 29:3387
Sikdar A, Panja SS, Biswas P, Roy S (2012) J Fluoresc 22:443
Stephen AE, McCormick CL (1992) Macromol 25:1881
Wei X, Hamley IW, Castelletto V et al (2004) Eur Polym J 40:47
Smith GL, McCormick CL (1998) Polym Prepr 39(1):310
General Administration of Quality Supervision, Inspection and Quarantine of the People’s Republic of China (AQSIQ). The Quality Inspection Standard of the People’s Republic of China GB12005.1–1989
Zhou P, Meng QT, He GJ, Wu HM, Duan CY, Quan X (2009) J Environ Monit 11:648
Yan FY, Cao DL, Wang M, Yang N, Yu QH, Dai LF, Chen L (2012) J Fluoresc 22:1249
Zhang D, Wang M, Chai MM, Che XP, Ye Y, Zhao YF (2012) Sens Actuators B: Chem 168:200
Tang LJ, Li Y, Nandhakumar R, Qian JH (2010) Monatsh Chem 141:615
Ma XI, Liu J, Du YG, Wei GH, Wei DB (2012) Scien China Chem 55(4):626
Yang XF, Liu P, Wang LP, Zhao ML (2008) J Fluoresc 18:453
Grabchev I, Dumas S, Chovelon JM (2008) Polym Adv Technol 19:316
Li NJ, Xu QF, Xia XW, Wang LH, Lu JM, Wen XW (2009) Mater Chem Phys 114:339
Grabchev I, Sali S, Betcheva R, Gregoriou V (2007) Eur Polym J 43:4297
Kaya İ, Kama M (2012) J Fluoresc 23(1):115
Wang BY, Liu XY, Ding SL, Su ZX (2011) J Polym Res 18:1315
Jeon YM, Kim BH, Kim JG, Gong MS (2006) Macromol Res 14(6):663
Luo J, Jiang SS, Qin SH, Wu HQ, Wang Y, Jiang JQ, Liu XY (2011) Sens Actuators B: Chem 160:1191
Acknowledgments
The authors are thankful for the financial support from National Natural Science Foundation of China (21001007, 21001008, 21171008).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Geng, TM., Wu, DY., Huang, W. et al. Fluorogenic detection of Hg2+, Cd2+, Fe2+, Pb2+ cations in aqueous media by means of an acrylamide-acrylic acid copolymer chemosensor with pendant rhodamine-based dyes. J Polym Res 21, 354 (2014). https://doi.org/10.1007/s10965-013-0354-7
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-013-0354-7