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Colorimetric chemosensor for Zn2+ based on pyrogallol red and poly(diallyldimethylammonium chloride) in aqueous solution

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Abstract

We report a new sensing strategy for Zn2+ by a colorimetric chemosensor based on commercially available negatively charged pyrogallol red (PR) and positively charged poly(diallyldimethylammonium chloride) (PDADMAC) ensemble in perfect aqueous solution at pH 7.0. The addition of ten equivalents of PDADMAC to PR resulted in PR aggregation by electrostatic interactions with PDADMAC. PR and PDADMAC ensemble showed a selective and distinct color change from red to blue in the presence of Zn2+ over other competitive metal ions. The color change was clearly visible to the naked eye, corresponding to a large red shift in the absorption peak from 544 to 595 nm. This result indicated that the PR and PDADMAC ensemble can serve as a potential candidate of a naked-eye chemosensor for Zn2+ in aqueous solution. This study demonstrates that the combination of organic dyes and oppositely charged polyelectrolytes is a versatile and useful tool, and shows great potential for the determination of important analytes in environmental and biological systems.

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References

  1. Quang DT, Kim JS (2010) Fluoro- and chromogenic chemodosimeters for heavy metal ion detection in solution and biospecimens. Chem Rev 110:6280–6301

    Article  CAS  Google Scholar 

  2. Sharma H, Kaur N, Singh A, Kuwar A, Singh N (2016) Optical chemosensors for water sample analysis. J Mater Chem C 4:5154–5194

    Article  CAS  Google Scholar 

  3. Jeong Y, Yoon J (2012) Recent progress on fluorescent chemosensors for metal ions. Inorg Chim Acta 381:2–14

    Article  CAS  Google Scholar 

  4. Outten CE, O’Halloran TV (2001) Femtomolar sensitivity of metalloregulatory proteins controlling zinc homeostasis. Science 292:2488–2492

    Article  CAS  Google Scholar 

  5. Berg JM, Shi Y (1996) The galvanization of biology: a growing appreciation for the roles of zinc. Science 271:1081–1085

    Article  CAS  Google Scholar 

  6. Frederickson CJ, Koh JY, Bush AI (2005) The neurobiology of zinc in health and disease. Nat Rev Neurosci 6:449–462

    Article  CAS  Google Scholar 

  7. Assaf SY, Chung SH (1984) Release of endogenous Zn2+ from brain-tissue during activity. Nature 308:734–736

    Article  CAS  Google Scholar 

  8. Bush AI, Pettingell WH, Multhaup G, Paradis M, Vonsattel JP, Gusella JF, Beyreuther K, Masters CL, Tanzi RE (1994) Rapid induction of Alzheimer A beta amyloid formation by zinc. Science 265:1464–1467

    Article  CAS  Google Scholar 

  9. Cuajungco MP, Lees GJ (1997) Zinc metabolism in the brain: relevance to human neurodegenerative disorders. Neurobiol Dis 4:137–169

    Article  CAS  Google Scholar 

  10. Onis M, Frongillo EA, Blcssner M (2000) Is malnutrition declining? An analysis of changes in levels of child malnutrition since 1980. Bull WHO 78:1222–1233

    Google Scholar 

  11. Walker CF, Black RE (2004) Zinc and the risk for infectious disease. Annu Rev Nutr 24:255–275

    Article  CAS  Google Scholar 

  12. Wang H, Sun CL, Yue YH, Yin FF, Jiang JQ, Wu HR, Zhang HL (2013) New molecular probe for the selective detection of zinc ion. Analyst 138:5576–5579

    Article  CAS  Google Scholar 

  13. Razi CH, Akelma AZ, Akin O, Kocak M, Ozdemir O, Celik A, Kislal FM (2012) Hair zinc and selenium levels in children with recurrent wheezing. Pediatr Pulmonol 47:1185–1191

    Article  Google Scholar 

  14. Priya MDL, Geetha A (2011) Level of trace elements (copper, zinc, magnesium and selenium) and toxic elements (lead and mercury) in the hair and nail of children with autism. Biol Trace Elem Res 142:148–158

    Article  Google Scholar 

  15. Buldini PL, Ferri D, Sharma JL (1997) Determination of some inorganic species in edible vegetable oils and fats by ion chromatography. J Chromatogr A 789:549–555

    Article  CAS  Google Scholar 

  16. Hu QF, Yang GY, Zhao YY, Yin JY (2003) Determination of copper, nickel, cobalt, silver, lead, cadmium, and mercury ions in water by solid-phase extraction and the RP-HPLC with UV–Vis detection. Anal Bioanal Chem 375:831–835

    Article  CAS  Google Scholar 

  17. Yue W, Bange A, Riehl BL, Johnson JM, Papautsky I, Heineman WR (2013) The application of nafion metal catalyst free carbon nanotube modified gold electrode: voltammetric zinc detection in serum. Electroanalysis 25:2259–2267

    CAS  Google Scholar 

  18. Carter KP, Young AM, Palmer AE (2014) Fluorescent sensors for measuring metal ions in living systems. Chem Rev 114:4564–4601

    Article  CAS  Google Scholar 

  19. Xu Z, Kim GH, Han SJ, Jou MJ, Lee C, Shin I, Yoon J (2009) An NBD-based colorimetric and fluorescent chemosensor for Zn2+ and its use for detection of intracellular zinc ions. Tetrahedron 65:2307–2312

    Article  CAS  Google Scholar 

  20. Kaur P, Kaur S, Mahajan A, Singh K (2008) Highly selective colorimetric sensor for Zn2+ based on hetarylazo derivative. Inorg Chem Commun 11:626–629

    Article  CAS  Google Scholar 

  21. Du P, Lippard SJ (2010) A highly selective turn-on colorimetric, red fluorescent sensor for detecting mobile zinc in living cells. Inorg Chem 49:10753–10755

    Article  CAS  Google Scholar 

  22. Ivanov VM, Mamedov AM (2006) 3,4,5-Trihydroxyfluorones as analytical reagents. J Anal Chem 61:1040–1062

    Article  CAS  Google Scholar 

  23. Ivanov VM, Mamedov AM (2006) Pyrogallol red and bromopyrogallol red in new optical methods for the determination of molybdenum(VI) and tungsten(VI). J Anal Chem 61:261–268

    Google Scholar 

  24. Pelit L, Koçak S, Pelit FO, Turkmena H, Ertas FN (2013) A spectrophotometric method for determination of molybdenum in water samples by using pyrogallol red and a water soluble ionic liquid. Anal Methods 5:5792–5798

    Article  CAS  Google Scholar 

  25. Higby K, Suiter CR, Silerkhodr T (1995) A comparison between two screening methods for detection of microproteinuria. Am J Obstet Gynecol 173:1111–1114

    Article  CAS  Google Scholar 

  26. Behr S, Trumel C, Palanche F, Braun JP (2003) Assessment of a pyrogallol red technique for total protein measurement in the cerebrospinal fluid of dogs. J Small Anim Pract 44:530–533

    Article  CAS  Google Scholar 

  27. Ensafi AA, Khayamian T, Khaloo SS (2004) Application of adsorptive cathodic differential pulse stripping method for simultaneous determination of copper and molybdenum using pyrogallol red. Anal Chim Acta 505:201–207

    Article  CAS  Google Scholar 

  28. Rojas C, Arancibia V, Gómez M, Nagles E (2012) Adsorptive stripping voltammetric determination of cobalt in the presence of nickel and zinc using pyrogallol red as chelating agent. Int J Electrochem Sci 7:979–990

    CAS  Google Scholar 

  29. Safavi A, Shams E (1999) Determination of trace amounts of copper(II) by adsorptive stripping voltammetry of its complex with pyrogallol red. Anal Chim Acta 385:265–272

    Article  CAS  Google Scholar 

  30. Arancibia V, Muñoz C (2007) Determination of aluminium in water samples by adsorptive cathodic stripping voltammetry in the presence of pyrogallol red and a quaternary ammonium salt. Talanta 73:546–552

    Article  CAS  Google Scholar 

  31. Guo H, Li Y, Chen X, Nie L, He N (2005) Determination of trace antimony (III) by adsorption voltammetry at carbon paste electrode. Sensors 5:284–292

    Article  CAS  Google Scholar 

  32. Sharma RK, Chelladurai C, Tiwari AD, Rajor HK, Mehta S, Otsuka M (2008) Studies on inhibition mechanism of transcription factor NF-κB and DNA binding by chelator pyrogallol red on the basis of its interaction with metal ions. Bioorg Med Chem 16:9018–9022

    Article  CAS  Google Scholar 

  33. Ensafi AA, Aboutalebi A (2005) A versatile stable cobalt optical sensor based on pyrogallol red immobilization on cellulose acetate film. Sens Actuators B 105:479–483

    Article  CAS  Google Scholar 

  34. Butler GB, Angelo RJ (1957) Preparation and polymerization of unsaturated quaternary ammonium compounds VIII A proposed alternating intramolecular-intermolecular chain propagation. J Am Chem Soc 79:3128–3131

    Article  CAS  Google Scholar 

  35. Assem Y, Chaffey-Millar H, Barner-Kowollik C, Wegner G, Agarwal S (2007) Controlled/living ring-closing cyclopolymerization of diallyldimethylammonium chloride via the reversible addition fragmentation chain transfer process. Macromolecules 2007:3907–3913

    Article  Google Scholar 

  36. Wang Y, Chen J, Jiao H, Chen Y, Li W, Zhang Q, Yu C (2013) Polymer-templated perylene-probe noncovalent self-assembly: a new strategy for label-free ultrasensitive fluorescence turn-on biosensing. Chem Eur J 19:12846–12852

    Article  CAS  Google Scholar 

  37. Dubas ST, Limsavarn L, Iamsamai C, Potiyaraj P (2006) Assembly of polyelectrolyte multilayers on nylon fibers. J Appl Polym Sci 101:3286–3290

    Article  CAS  Google Scholar 

  38. Job P (1928) Formation and stability of inorganic complexes in solution. Ann Chim-Puris 9:113–203

    CAS  Google Scholar 

  39. Irving HMNH, Freiser H, West TS (1978) IUPAC compendium of analytical nomenclature, definitive rules. Pergamon Press, Oxford

    Google Scholar 

  40. Benesi AH, Hildebrand HJ (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707

    Article  CAS  Google Scholar 

  41. Dahm KG, Guerra KL, Xu P, Drewes JE (2011) Composite geochemical database for coalbed methane produced water quality in the rocky mountain region. Environ Sci Technol 45:7655–7663

    Article  CAS  Google Scholar 

  42. WHO (2008) Guidelines for drinking water quality, Geneva

  43. Kumar YP, King P, Prasad VSKR (2006) Zinc biosorption on Tectona grandis L.f. leaves biomass:equilibrium and kinetic studies. Chem Eng J 124:63–70

    Article  CAS  Google Scholar 

  44. 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 42:16569–16577

    Article  CAS  Google Scholar 

  45. Tsikalas GK, Lazarou P, Klontzas E, Pergantis SA, Spanopoulos I, Trikalitis PN, Froudakis GE, Katerinopoulos HE (2014) A “turn-on”-turning-to-ratiometric sensor for zinc(II) ions in aqueous media. RSC Adv 4:693–696

    Article  CAS  Google Scholar 

  46. 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 42:16569–16577

    Article  CAS  Google Scholar 

  47. Kim TS, Lee JJ, Lee SY, Jo TG, Kim C (2016) A highly sensitive benzimidazole-based chemosensor for the colorimetric detection of Fe(II) and Fe(III) and the fluorometric detection of Zn(II) in aqueous media. RSC Adv 6:61505–61515

    Article  CAS  Google Scholar 

  48. Li M, Lu HY, Liu RL, Chen JD, Chen CF (2012) Turn-on fluorescent sensor for selective detection of Zn2+, Cd2+, and Hg2+ in water. J Org Chem 77:3670–3673

    Article  CAS  Google Scholar 

  49. Mikata Y, Kawata K, Takeuchi S, Nakanishi K, Konno H, Itami S, Yasuda K, Tamotsu S, Burdette SC (2014) Isoquinoline-derivatized tris(2-pyridylmethyl)-amines as fluorescent zinc sensors with strict Zn2+/Cd2+ selectivity. Dalton Trans 43:10751–10759

    Article  CAS  Google Scholar 

  50. Aragoni MC, Arca M, Bencini A, Caltagirone C, Garau A, Isaia F, Light ME, Lippolis V, Lodeiro C, Mameli M, Montis R, Mostallino MC, Pintusa A, Puccioni S (2013) Zn2+/Cd2+ optical discrimination by fluorescent chemosensors based on 8-hydroxyquinoline derivatives and sulfur-containing macrocyclic units. Dalton Trans 42:14516–14530

    Article  CAS  Google Scholar 

  51. Madden T, Datye A, Fulton M, Prairie M, Majumdar S, Stange B (1997) Oxidation of metal-EDTA complexes by TiO2 photocatalysis. Environ Sci Technol 31:3475–3481

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Faculty of Science and Engineering, Toyo University, 2100 Kujirai, Kawagoe, Saitama, 350-8585, Japan

    Masaru Sakamaki & Yasumasa Fukushima

  2. Research Institute of Industrial Technology, Toyo University, 2100 Kujirai, Kawagoe, Saitama, 350-8585, Japan

    Shunichi Aikawa

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  1. Masaru Sakamaki
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  2. Shunichi Aikawa
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  3. Yasumasa Fukushima
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Correspondence to Yasumasa Fukushima.

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Sakamaki, M., Aikawa, S. & Fukushima, Y. Colorimetric chemosensor for Zn2+ based on pyrogallol red and poly(diallyldimethylammonium chloride) in aqueous solution. Polym. Bull. 75, 1667–1680 (2018). https://doi.org/10.1007/s00289-017-2119-7

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  • DOI: https://doi.org/10.1007/s00289-017-2119-7

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