Abstract
A novel 8-hydroxyquinoline-based fluorescent and colorimetric chemosensor was designed, synthesized and fully characterized. The sensor showed high selectivity and sensitivity toward Al3+ over other tested cations in EtOH/H2O (1:99, v/v) medium. The increase in fluorescence intensity was linearly proportional to the concentration of Al3+ with a detection limit of 7.38 × 10−6 M. Moreover, the sensor exhibited an obvious color change from yellow to black in the presence of Fe2+ and Fe3+ in EtOH/THF (99:1, v/v) solution. The absorbance changes showed a linear response to iron ions with the detection limits of 4.24 × 10−7 M and 5.60 × 10−7 M for Fe2+ and Fe3+, respectively. Thus, this chemosensor provides a novel approach for selectively recognition of Al3+, Fe3+ and Fe2+ among environmentally relevant metal ions.
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References
Banks WA, Kastin AJ (1989) Aluminum-Induced neurotoxicity: Alterations in membrane function at the blood-brain barrier. Neurosci Biobehav Rev 13(1):47–53
Nayak P (2002) Aluminum: impacts and disease. Environ Res 89(2):101–115
Good PF, Olanow CW, Perl DP (1992) Neuromelanin-containing neurons of the substantia nigra accumulate iron and aluminum in Parkinson’s disease: a LAMMA study. Brain Res 593(2):343–346
Walton JR (2007) An aluminum-based rat model for Alzheimer’s disease exhibits oxidative damage, inhibition of PP2A activity, hyperphosphorylated tau, and granulovacuolar degeneration. J Inorg Biochem 101(9):1275–1284
Darbre PD (2005) Aluminium, antiperspirants and breast cancer. J Inorg Biochem 99(9):1912–1919
Alvim MN, Ramos FT, Oliveira DC, Isaias RM, Franca MG (2012) Aluminium localization and toxicity symptoms related to root growth inhibition in rice (Oryza sativa L.) seedlings. J Biosci 37(6):1079–1088
Poléo ABS (1995) Aluminium polymerization — A mechanism of acute toxicity of aqueous aluminium to fish. Aquat Toxicol 31(4):347–356
Liu X, Theil EC (2005) Ferritins: Dynamic management of biological iron and oxygen chemistry. Acc Chem Res 38(3):167–175
Kustka A, Carpenter EJ, Sañudo-Wilhelmy SA (2002) Iron and marine nitrogen fixation: progress and future directions. Res Microbiol 153(5):255–262
Wójciak RW, Mojs E, Stanislawska-Kubiak M (2014) The occurrence of iron-deficiency anemia in children with type 1 diabetes. J Investig Med 62(6):865–867
Simcox JA, McClain DA (2013) Iron and diabetes risk. Cell Metab 17(3):329–341
Weinreb O, Mandel S, Youdim MBH, Amit T (2013) Targeting dysregulation of brain iron homeostasis in Parkinson’s disease by iron chelators. Free Radic Biol Med 62:52–64
Torti SV, Torti FM (2013) Iron and cancer: more ore to be mined. Nat Rev Cancer 13(5):342–355
Unsal YE, Soylak M, Tuzen M, Hazer B (2015) Determination of lead, copper, and iron in cosmetics, water, soil, and food using polyhydroxybutyrate-B-polydimethyl siloxane preconcentration and flame atomic absorption spectrometry. Anal Lett 48(7):1163–1179
Ulusoy Hİ, Gürkan R, Aksoy Ü, Akçay M (2011) Development of a cloud point extraction and preconcentration method for determination of trace aluminum in mineral waters by FAAS. Microchem J 99(1):76–81
Sooriyaarachchi M, Gailer J (2010) Removal of Fe3+ and Zn2+ from plasma metalloproteins by iron chelating therapeutics depicted with SEC-ICP-AES. Dalton Trans 39(32):7466–7473
Frankowski M, Zioła-Frankowska A, Kurzyca I, Novotný K, Vaculovič T, Kanický V, Siepak M, Siepak J (2011) Determination of aluminium in groundwater samples by GF-AAS, ICP-AES, ICP-MS and modelling of inorganic aluminium complexes. Environ Monit Assess 182(1–4):71–84
Das S, Dutta M, Das D (2013) Fluorescent probes for selective determination of trace level Al3+: Recent developments and future prospects. Anal Methods 5(22):6262–6285
Sahoo SK, Sharma D, Bera RK, Crisponi G, Callan JF (2012) Iron(III) selective molecular and supramolecular fluorescent probes. Chem Soc Rev 41(21):7195–7227
Yi C, Song B, Tian W, Cui X, Qi Q, Jiang W, Qi Z, Sun Y (2014) Fluorescent sensor of fluorene derivatives having phosphonic acid as a fluorogenic ionophore: Synthesis and static quenched properties for Fe(III). Tetrahedron Lett 55(37):5119–5123
Zhang G, Lu B, Wen Y, Lu L, Xu J (2012) Facile fabrication of a cost-effective, water-soluble, and electrosynthesized poly(9-aminofluorene) fluorescent sensor for the selective and sensitive detection of Fe(III) and inorganic phosphates. Sensors Actuators B Chem 171–172:786–794
Huang L, Hou F, Cheng J, Xi P, Chen F, Bai D, Zeng Z (2012) Selective off-on fluorescent chemosensor for detection of Fe3+ ions in aqueous media. Org Biomol Chem 10(48):9634–9638
Jiménez-Sánchez A, Ortiz B, Navarrete VO, Flores JC, Farfán N, Santillan R (2015) A dual-model fluorescent Zn2+/Cu2+ ions sensor with in-situ detection of S2−/(PO4)− and colorimetric detection of Fe2+ ion. Inorg Chim Acta 429:243–251
Santhoshkumar S, Velmurugan K, Prabhu J, Radhakrishnan G, Nandhakumar R (2016) A naphthalene derived Schiff base as a selective fluorescent probe for Fe2+. Inorg Chim Acta 439:1–7
Singh G, Singh J, Mangat SS (2015) Design of selective 8-methylquinolinol based ratiometric Fe2+ and Fe3+/H2PO4 − fluorescent chemosensor mimicking NOR and IMPLICATION logic gates. J Lumin 165:123–129
Kim KB, Kim H, Song EJ, Kim S, Noh I, Kim C (2013) A cap-type Schiff base acting as a fluorescence sensor for zinc(II) and a colorimetric sensor for iron(II), copper(II), and zinc(II) in aqueous media. Dalton Trans 42(47):16569–16577
Li CR, Liao ZC, Qin JC, Wang BD, Yang ZY (2015) Study on 2-acetylpyrazine (pyridine-2′-acetyl) Hydrazone as a fluorescent sensor for Al3+. J Lumin 168:330–333
Chen CH, Liao DJ, Wan CF, Wu AT (2013) A turn-on and reversible Schiff base fluorescence sensor for Al3+ ion. Analyst 138(9):2527–2530
Gou C, Qin SH, Wu HQ, Wang Y, Luo J, Liu XY (2011) A highly selective chemosensor for Cu2+ and Al3+ in two different ways based on salicylaldehyde Schiff. Inorg Chem Commun 14(10):1622–1625
Wang G-q, Qin J-c, Li C-R, Yang Z-y (2015) A highly selective fluorescent probe for Al3+ based on quinoline derivative. Spectrochim Acta A 150:21–25
An J, Li T, Wang B, Yang Z, Yan M (2014) An off-on fluorescent sensor with high selectivity and sensitivity for Fe(III). J Coord Chem 67(5):921–928
Qin JC, Cheng XY, Fang R, Wang MF, Yang ZY, Li TR, Li Y (2016) Two Schiff-base fluorescent sensors for selective sensing of aluminum (III): Experimental and computational studies. Spectrochim Acta A 152:352–357
Fan L, Li TR, Wang BD, Yang ZY, Liu CJ (2014) A colorimetric and turn-on fluorescent chemosensor for Al(III) based on a chromone Schiff-base. Spectrochim Acta A 118:760–764
Qin J-c, Li T-r, Wang B-d, Yang Z-y, Fan L (2014) Fluorescent sensor for selective detection of Al3+ based on quinoline–coumarin conjugate. Spectrochim Acta A 133:38–43
Sen S, Sarkar S, Chattopadhyay B, Moirangthem A, Basu A, Dhara K, Chattopadhyay P (2012) A ratiometric fluorescent chemosensor for iron: discrimination of Fe2+ and Fe3+ and living cell application. Analyst 137(14):3335–3342
Aydin Z, Wei Y, Guo M (2012) A highly selective rhodamine based turn-on optical sensor for Fe3+. Inorg Chem Commun 20:93–96
Devaraj S, Tsui YK, Chiang CY, Yen YP (2012) A new dual functional sensor: Highly selective colorimetric chemosensor for Fe3+ and fluorescent sensor for Mg2+. Spectrochim Acta A 96:594–599
Choi YW, Park GJ, Na YJ, Jo HY, Lee SA, You GR, Kim C (2014) A single schiff base molecule for recognizing multiple metal ions: A fluorescence sensor for Zn(II) and Al(III) and colorimetric sensor for Fe(II) and Fe(III). Sensors Actuators B Chem 194:343–352
Bronson RT, Bradshaw JS, Savage PB, Fuangswasdi S, Lee SC, Krakowiak KE, Izatt RM (2001) Bis-8-hydroxyquinoline-armed diazatrithia-15-crown-5 and diazatrithia-16-crown-5 ligands: Possible fluorophoric metal ion sensors. J Organomet Chem 66(14):4752–4758
Farruggia G, Iotti S, Prodi L, Montalti M, Zaccheroni N, Savage PB, Trapani V, Sale P, Wolf FI (2006) 8-Hydroxyquinoline derivatives as fluorescent sensors for magnesium in living cells. J Am Chem Soc 128(1):344–350
Song EJ, Park GJ, Lee JJ, Lee S, Noh I, Kim Y, Kim S-J, Kim C, Harrison RG (2015) A fluorescence sensor for Zn2+ that also acts as a visible sensor for Co2+ and Cu2+. Sensors Actuators B Chem 213:268–275
Vaswani KG, Keränen MD (2009) Detection of aqueous mercuric ion with a structurally simple 8-hydroxyquinoline derived on-off fluorosensor. Inorg Chem 48(13):5797–5800
Zhao Y, Lin Z, Liao H, Duan C, Meng Q (2006) A highly selective fluorescent chemosensor for Al3+ derivated from 8-hydroxyquinoline. Inorg Chem Commun 9(9):966–968
Jiang XH, Wang BD, Yang ZY, Liu YC, Li TR, Liu ZC (2011) 8-Hydroxyquinoline-5-carbaldehyde Schiff-base as a highly selective and sensitive Al3+ sensor in weak acid aqueous medium. Inorg Chem Commun 14(8):1224–1227
Fan L, Jiang XH, Wang BD, Yang ZY (2014) 4-(8′-Hydroxyquinolin-7′-yl)methyleneimino-1-phenyl-2,3-dimethyl-5-pyzole as a fluorescent chemosensor for aluminum ion in acid aqueous medium. Sensors Actuators B Chem 205:249–254
Ramos ML, Justino LLG, Salvador AIN, De Sousa ARE, Abreu PE, Fonseca SM, Burrows HD (2012) NMR, DFT and luminescence studies of the complexation of Al(III) With 8-hydroxyquinoline-5-sulfonate. Dalton Trans 41(40):12478–12489
Pierre J-L, Baret P, Serratrice G (2003) Hydroxyquinolines as iron chelators. Curr Med Chem 10:1077–1084
Li Z, Li H, Shi C, Zhang W, Zhou W, Wei L, Yu M (2016) Naked-eye-based highly selective sensing of Fe3+ and further for PPi with nano copolymer film. Sensors Actuators B Chem 226:127–134
Zarabadi-Poor P, Badiei A, Yousefi AA, Barroso-Flores J (2013) Selective optical sensing of Hg(II) in aqueous media by H-Acid/SBA-15: A combined experimental and theoretical study. J Phys Chem C 117(18):9281–9289
Karimi M, Badiei A, Mohammadi Ziarani G (2015) A novel naphthalene-immobilized nanoporous SBA-15 as a highly selective optical sensor for detection of Fe3+ in water. J Fluoresc 25(5):1297–1302
Afshani J, Badiei A, Karimi M, Lashgari N, Mohammadi Ziarani G (2016) A single fluorescent sensor for Hg2+ and discriminately detection of Cr3+ and Cr(VI). J Fluoresc 26:263–270
Karimi M, Badiei A, Mohammadi Ziarani G (2015) A single hybrid optical sensor based on nanoporous silica type SBA-15 for detection of Pb2+ and I− in aqueous media. RSC Adv 5(46):36530–36539
Wang F, Peng R, Sha Y (2008) Selective dendritic fluorescent sensors for Zn(II). Molecules 13(4):922–930
Maity D, Govindaraju T (2010) Conformationally constrained (coumarin − triazolyl − bipyridyl) click fluoroionophore as a selective Al3+ sensor. Inorg Chem 49(16):7229–7231
Kim S, Noh JY, Kim KY, Kim JH, Kang HK, Nam SW, Kim SH, Park S, Kim C, Kim J (2012) Salicylimine-based fluorescent chemosensor for aluminum ions and application to bioimaging. Inorg Chem 51(6):3597–3602
Qin JC, Yang ZY (2015) Selective fluorescent sensor for Al3+ using a novel quinoline derivative in aqueous solution. Synth Metals 209:570–576
Bardez E, Devol I, Larrey B, Valeur B (1997) Excited-state processes in 8-hydroxyquinoline: Photoinduced tautomerization and solvation effects. J Phys Chem B 101(39):7786–7793
Huston ME, Haider KW, Czarnik AW (1988) Chelation enhanced fluorescence in 9,10-bis[[(2-(dimethylamino)ethyl)methylamino]methyl]anthracene. J Am Chem Soc 110(13):4460–4462
Bronson RT, Montalti M, Prodi L, Zaccheroni N, Lamb RD, Dalley NK, Izatt RM, Bradshaw JS, Savage PB (2004) Origins of ‘on–off’ fluorescent behavior of 8-hydroxyquinoline containing chemosensors. Tetrahedron 60(49):11139–11144
Erdemir S, Kocyigit O, Karakurt S (2015) A new perylene bisimide-armed calix[4]-aza-crown as "turn on" fluorescent sensor for Hg2+ ion and its application to living cells. Sensors Actuators B Chem 220:381–388
Afshani J, Badiei A, Lashgari N, Mohammadi Ziarani G (2016) A simple nanoporous silica-based dual mode optical sensor for detection of multiple analytes (Fe3+, Al3+ and CN−) in water mimicking XOR logic gate. RSC Adv 6(7):5957–5964
Meier MAR, Schubert US (2005) Fluorescent sensing of transition metal ions based on the encapsulation of dithranol in a polymeric core shell architecture. Chem Commun. doi:10.1039/b505409e
Hao E, Meng T, Zhang M, Pang W, Zhou Y, Jiao L (2011) Solvent dependent fluorescent properties of a 1,2,3-triazole linked 8-hydroxyquinoline chemosensor: tunable detection from zinc(II) to iron(III) in the CH3CN/H2O system. J Phys Chem A 115(29):8234–8241
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The authors thank the research council of University of Tehran for financial support.
This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.
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Lashgari, N., Badiei, A. & Mohammadi Ziarani, G. A Fluorescent Sensor for Al(III) and Colorimetric Sensor for Fe(III) and Fe(II) Based on a Novel 8-Hydroxyquinoline Derivative. J Fluoresc 26, 1885–1894 (2016). https://doi.org/10.1007/s10895-016-1883-3
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DOI: https://doi.org/10.1007/s10895-016-1883-3