Journal of Fluorescence

, Volume 25, Issue 5, pp 1339–1349 | Cite as

2,4-Diamino-6-Hydroxypyrimidine Based Poly(azomethine-Urethane): Synthesis and Application as a Fluorescent Probe for Detection of Cu2+ in Aqueous Solution



A novel poly(azomethine-urethane)-based 2,4-diamino-6-hydroxyprimidine was synthesized with chemical reaction and it designed as fluorescence probe for determination of Cu2+ in aqueous solution. The photoluminescence (PL) characteristic of the prepared Schiff base (HPAMP) and its poly(azomethine-urethane) (P-HPAMP) derivative were investigated in different polarity solvents suh as MeOH, THF and DMF. PL measurements showed that both HPAMP and P-HPAMP have higher emission intensity and Stoke’s shift value (ΔλST) in THF than the other solvents. Also, the proposed probe exhibited a specific fluorescent on response to Cu2+ over the other tested transition metal ions in aqueous solution. The sensor gave highly selective and sensetive response against Cu2+ as increasing a new emission peak at 341 nm, and possible interference and quenching effect of the other tested transition metal ions were found too low. Detection limit of Cu2+ sensor was also calculated as 7.87 × 10−6 mol L−1 in THF/deionized water (1:2, v:v).


Poly(azomethine-urethane) Fluorescent sensor Cu(II) sensor Copper Schiff base 



The authors would like to thank Government Planning Organization for the financial support (Project No: GPO2010K120710).


  1. 1.
    Wang L, Qin W, Liu W (2014) Two highly sensitive Schiff-base fluorescent indicators for the detection of Zn2+. Anal Methods 6:1167–1173CrossRefGoogle Scholar
  2. 2.
    Nandre J, Patil S, Patil P, Sahoo S, Redshaw C, Mahulikar P, Patil U (2014) The amidine based colorimetric sensor for Fe3+, Fe2+, and Cu2+ in aqueous medium. J Fluoresc 24:1563–1570CrossRefPubMedGoogle Scholar
  3. 3.
    Cao H, Chen Z, Zheng H, Huang Y (2014) Copper nanoclusters as a highly sensitive and selective fluorescence sensor for ferric ions in serum and living cells by imaging. Biosens Bioelectron 62:189–195CrossRefPubMedGoogle Scholar
  4. 4.
    Zhao Q, Li RF, Xing SK, Liu XM, Hu TL, Bu XH (2011) A highly selective on/off fluorescence sensor for cadmium(II). Inorg Chem 50:10041–10046CrossRefPubMedGoogle Scholar
  5. 5.
    Lohani CR, Lee KH (2010) The effect of absorbance of Fe3+ on the detection of Fe3+ by fluorescent chemical sensors. Sensors Actuators B-Chem 143:649–654CrossRefGoogle Scholar
  6. 6.
    Duan YW, Tang HY, Guo Y, Song ZK, Peng MJ, Yong YY (2010) The synthesis and study of the fluorescent probe for sensing Cu2+ based on a novel coumarin Schiff-base. Chin Chem Lett 25:1082–1086CrossRefGoogle Scholar
  7. 7.
    Jayabharathi J, Thanikachalam V, Jayamoorthy K, Perumal MV (2011) A physiochemical study of excited state intramolecular proton transfer process Luminescent chemosensor by spectroscopic investigation supported by ab initio calculations. Spectrochim Acta A-M 79:6–16CrossRefGoogle Scholar
  8. 8.
    Qiu X, Han S, Hu Y, Gao M, Wang H (2014) Periodic mesoporous organosilicas for ultra-high selective copper(II) detection and sensing mechanism. J Mater Chem A 2:1493–1501CrossRefGoogle Scholar
  9. 9.
    Tang L, Wu D, Hou H, Wen X, Dai X (2014) A Simple carbazole-based Schiff base as fluorescence “off-on” probe for highly selective recognition of Cu2+ in aqueous solution. Bull Korean Chem Soc 35:2326–2330CrossRefGoogle Scholar
  10. 10.
    Cao W, Zheng XJ, Fang DC, Jin LP (2014) A highly selective and sensitive Zn(II) complex based chemosensor for sequential recognition of Cu(II) and cyanide. Dalton Trans 43:7298–7303CrossRefPubMedGoogle Scholar
  11. 11.
    Zou C, Gao L, Liu T, Xu Z, Cui J (2014) A fluorescent probe based on N-butylbenzene-1,2-diamine for Cu(II) and its imaging in living cells. J Incl Phenom Macrocycl Chem 80:383–390CrossRefGoogle Scholar
  12. 12.
    Fahrni CJ (2013) Synthetic fluorescent probes for monovalent copper. Curr Opin Chem Biol 17:656–662PubMedCentralCrossRefPubMedGoogle Scholar
  13. 13.
    Khatua S, Choi SH, Lee J, Huh JO, Do Y, Churchill DG (2009) Highly selective fluorescence detection of Cu2+ in water by chiral dimeric Zn2+ complexes through direct displacement. Inorg Chem 48:1799–1801CrossRefPubMedGoogle Scholar
  14. 14.
    Que EL, Domaille DW, Chang CJ (2008) Metals in neurobiology: probing their chemistry and biology with molecular imaging. Chem Rev 108:1517–1549CrossRefPubMedGoogle Scholar
  15. 15.
    García-Beltrán O, Mena N, Friedrich LC, Netto-Ferreira JC, Vargas V, Quina FH, Núñez MT, Cassels BK (2012) Design and synthesis of a new coumarin-based ‘turn-on’ fluorescent probe selective for Cu+2. Tetrahedron Lett 53:5280–5283CrossRefGoogle Scholar
  16. 16.
    Tyagi M, Chandra S, Tyagi P (2014) Mn(II) and Cu(II) complexes of a bidentate Schiff’s base ligand: spectral, thermal, molecular modelling and mycological studies. Spectrochim Acta A-M 117:1–8CrossRefGoogle Scholar
  17. 17.
    Roy N, Pramanik HAR, Paul PC, Singh ST (2014) A sensitive Schiff-base fluorescent chemosensor for the selective detection of Zn2+. J Fluoresc 24:1099–1106CrossRefPubMedGoogle Scholar
  18. 18.
    Salmon L, Thuéry P, Rivière E, Ephritikhine M (2006) Synthesis, structure and magnetic behavior of a series of trinuclear Schiff base complexes of 5f (UIV, ThIV) and 3d (CuII, ZnII) ions. Inorg Chem 45:83–93CrossRefPubMedGoogle Scholar
  19. 19.
    Na YJ, Choi YW, Yun JY, Park KM, Chang PS, Kim C (2015) Dual-channel detection of Cu2+ and F with a simple Schiff-based colorimetric and fluorescent sensor. Spectrochim Acta A 36:1649–1657CrossRefGoogle Scholar
  20. 20.
    Zhang P, Chen J, Huang F, Zeng Z, Hu J, Yi P, Zeng F, Wu S (2013) One-pot fabrication of polymer nanoparticle-based chemosensors for Cu2+ detection in aqueous media. Polym Chem 4:2325–2332CrossRefGoogle Scholar
  21. 21.
    Chen J, Li Y, Zhong W, Hou Q, Wang H, Sun X, Yi P (2015) Novel fluorescent polymeric nanoparticles for highly selective recognition of copper ion and sulfide anion in water. Sensors Actuators B-Chem 206:230–238CrossRefGoogle Scholar
  22. 22.
    Kaya İ, Yıldırım M, Kamacı M (2011) A new kind of optical Mn(II) sensor with high selectivity: melamine based poly(azomethine–urethane). Synth Met 161:2036–2040CrossRefGoogle Scholar
  23. 23.
    Kaya İ, Kamacı M (2013) Highly selective and stable florescent sensor for Cd(II) based on poly(azomethine-urethane). J Fluoresc 23:115–121CrossRefPubMedGoogle Scholar
  24. 24.
    Kamacı M, Kaya İ (2015) The novel Poly(azomethine-urethane): synthesis, morphological properties and application as a fluorescent probe for detection of Zn2+ Ions. J Inorg Organomet Polym. doi: 10.1007/s10904-015-0234-1 Google Scholar
  25. 25.
    Kamacı M, Kaya İ (2014) Synthesis, thermal and morphological properties of polyurethanes containing azomethine linkage. J Inorg Organomet Polym 24:803–818CrossRefGoogle Scholar
  26. 26.
    Kamacı M, Kaya İ (2014) Photophysical, electrochemical, thermal and morphological properties of polyurethanes containing azomethine bonding. J Macromol Sci A 51:805–819CrossRefGoogle Scholar
  27. 27.
    Ben-nan C, Qin H, Yan H, Chun-man J, Qi Z (2013) Highly sensitive and selective chemosensor for Cu2+ based on a Schiff base. Chem Res Chin Univ 29:419–423CrossRefGoogle Scholar
  28. 28.
    Kamacı M, Kaya İ (2013) Synthesis of metal-coordinated poly(azomethine-urethane)s: thermal stability, optical and electrochemical properties. J Inorg Organomet Polym 23:1159–1171CrossRefGoogle Scholar
  29. 29.
    Yang X, Lyu H, Chen K, Zhu X, Zhang S, Chen J (2014) Selective extraction of bio-oil from hydrothermal liquefaction of salix psammophila by organic solvents with different polarities through multistep extraction separation. Bio Res 9:5219–5233Google Scholar
  30. 30.
    Yushchenko DA, Shvadchak VV, Bilokin’ MD, Klymchenko AS, Duportail G, Mely Y, Pivovarenko VG (2006) Modulation of dual fluorescence in a 3-hydroxyquinolone dye by perturbation of its intramolecular proton transfer with solvent polarity and basicity. Photochem Photobiol Sci 5:1038–1044CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.Polymer Synthesis and Analysis Lab., Department of ChemistryÇanakkale Onsekiz Mart UniversityÇanakkaleTurkey
  2. 2.Department of Chemistry, Faculty of Sciences and LettersPiri Reis UniversityIstanbulTurkey

Personalised recommendations