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New Colorimetric and Fluorometric Fluoride Ion Probe Based on Anthra[1,9-cd]pyrazol-6(2H)-one

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Abstract

New colorimetric and fluorometric fluoride ion probe, anthra[1,9-cd]pyrazol- 6(2H)-one (1), was synthesized by one-step condensation. The probe 1 shows F-selective color change from colorless to pink and appearance of red fluorescence. The fluorescence quantum yield of free probe 1 in DMSO was calculated to be 0.03. After addition of 15 equiv. of F, its fluorescence quantum yield can be increased to 0.37. The analytical detection limit for F was 2.8 × 10− 7 M. 1H NMR analysis and DFT calculation show that the F-induced colorimetric and fluorometric responses of 1 are driven by deprotonation process.

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References

  1. 1.

    Kirk KL (1995) Biochemistry of the halogens and inorganic halides. Plenum Pless, New York, p 58

  2. 2.

    Kleerekoper M (1998) The role of fluoride in the prevention of osteoporosis. Endocrinol Metab Clin N Am 27:441–452

  3. 3.

    Gavrilescu M, Pavel LV, Cretescu I (2009) Characterization and remediation of soils contaminated with uranium. J Hazard Mater 163:475–510

  4. 4.

    John GH, May I, Collison D, Helliwell M (2004) Synthesis, structural and spectroscopic characterisation of three di-μ-fluoro-bis [dioxouranyl] complexes. Polyhedron 23:3097–3103

  5. 5.

    Seneda J, Figueiredo F, Abrao A, Carvalho F, Frajndlich E (2001) J Alloys Compd 323:838–841

  6. 6.

    Matuso S, Kiyomiya KI, Kurebe M (1998) Mechanism of toxic action of fluoride in dental fluorosis: whether trimeric G proteins participate in the disturbance of intracellular transport of secretory ameloblast exposed fluoride. Arch Toxicol 72:798–806

  7. 7.

    Weatherall JA (1969) Pharmacology of fluorides. In: Handbook of experimental pharmacology XX/1. Springer-Verlag, Berlin, pp 141–172 Part 1

  8. 8.

    Willard HH, Winter OB (1933) Volumetric method for determination of fluorine. Ind Eng Chem Anal Ed 5:7–10

  9. 9.

    De Marco R, Clarke G, Pejcic B (2007) Ion-selective electrode potentiometry in environmental analysis. Electroanalysis 19:1987–2001

  10. 10.

    van den Hoop MAGT, Cleven RFMJ, van Staden JJ, Neele JJ (1996) Analysis of fluoride in rain water comparison of capillary electrophoresis with ionchromatography and ion-selective electrode potentiometry. J Chromatogr A 739:241–248

  11. 11.

    Suksai C, Tuntulani T (2003) Chromogenic anion sensors. Chem Soc Rev 32:192–202

  12. 12.

    Cao YC (2015) A capillary based chemiluminscent multi-target immunoassay. J Fluoresc 25:563–568

  13. 13.

    Liu C, Zhou Z, Zou L, Cao YC, Liu JA, Lin Y (2016) High sensitivity bacillus thuringiensis cry1Ac protein detections using fluorescein diacetate nanoparticles. J Fluoresc 26:451–457

  14. 14.

    Okutan E, Tümay SO, Yeşilot S (2016) Colorimetric fluorescent sensors for hemoglobin based on BODIPY dyes. J Fluoresc 26:2333–2343

  15. 15.

    de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley ATM, McCoy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566

  16. 16.

    Cao YC, Wang Z, Yang R, Zou L, Zhou Z, Mi T, Shi H (2016) Quantum dots encoded Au coated polystyrene bead arranged micro-channel for multiplex arrays. Talanta 146:749–753

  17. 17.

    Lu W, Zhang M, Liu K, Fan B, Xia Z, Jiang L (2011) A fluoride-selective colorimetric and fluorescent chemosensor and its use for the design of molecular-scale logic devices. Sensors Actuators B 160:1005–1010

  18. 18.

    Thiagarajan V, Ramamurthy P, Thirumalai D, Ramakrishnan VT (2005) A novel colorimetric and fluorescent chemosensor for anions involving PET and ICT pathways. Org Lett 7:657–660

  19. 19.

    Santos-Figueroa LE, Moragues ME, Raposo MM, Batista RM, Costa SP, Ferreira RC, Sancenon F, Martinez-Manez R, Ros-Lis JV, Soto J (2012) HBT-based chemosensors for the detection of fluoride through deprotonation process: experimental and DFT studies. Org Biomol Chem 10:7418–7428

  20. 20.

    Cho EJ, Moon JW, Ko SW, Lee JY, Kim SK, Yoon J, Nam KC (2003) A new fluoride selective fluorescent as well as chromogenic chemosensor containing a naphthalene urea derivative. J Am Chem Soc 125:12376–12377

  21. 21.

    Wu Y, Peng X, Fan J, Gao S, Tian M, Zhao J, Sun S (2007) Fluorescence sensing of anions based on inhibition of excited-state intramolecular proton transfer. J Org Chem 72:62–70

  22. 22.

    Ke B, Chen W, Ni N, Cheng Y, Dai C, Dinh H, Wang B (2013) A fluorescent probe for rapid aqueous fluoride detection and cell imaging. Chem Commun 49:2494–2496

  23. 23.

    Zhao P, Jiang J, Leng B, Tian H (2009) Polymer fluoride sensors synthesized by RAFT polymerization. Rapid Commun 30:1715–1718

  24. 24.

    Hung HC, Chang YY, Luo L, Hung CH, Diau EW, Chung WS (2014) Different sensing modes of fluoride and acetate based on a calix [4] arene with 25, 27-bistriazolylmethylpyrenylacetamides. Photochem Photobiol Sci 13:370–379

  25. 25.

    Bhosale SV, Bhosale SV, Kalyankar MB, Langford SJ (2009) A core- substituted naphthalene diimide fluoride sensor. Org Lett 11:5418–5421

  26. 26.

    Im HG, Kim HY, Choi MG, Chang SK (2013) Reaction-based dual signaling of fluoride ions by resorufin sulfonates. Org Biomol Chem 11:2966–2971

  27. 27.

    Fu L, Tian FF, Lai L, Liu Y, Harvey PD, Jiang FL (2014) A ratiometric “two-in-one” fluorescent chemodosimeter for fluoride and hydrogen sulfide. Sensors Actuators B 193:701–707

  28. 28.

    Lee HN, Singh NJ, Kim SK, Kwon JY. Kim YY, Kim KS, Yoon J (2007) New imidazolium systems bearing two pyrene groups as fluorescent chemosensors for anions and anion induced logic gates. Tetrahedron Lett 48:169–172

  29. 29.

    Yoon J, Kim SK, Singh NJ, Kim KS (2006) Imidazolium receptors for the recognition of anions. Chem Soc Rev 35:355–360

  30. 30.

    Jeyanthi D, Iniya M, Krishnaveni K, Chellappa D (2015) Novel indole based dual responsive “turn-on” chemosensor for fluoride ion detection. Spectrochim Acta A 136:1269–1274

  31. 31.

    Shiraishi Y, Maehara H, Hirai T (2009) Indole-azadiene conjugate as a colorimetric and fluorometric probe for selective fluoride ion sensing. Org Biomol Chem 7:2072–2076

  32. 32.

    Mahapatra AK, Maji R, Maiti K, Adhikari SS, Das Mukhopadhyay C, Mandal D (2014) Ratiometric sensing of fluoride and acetate anions based on a BODIPY-azaindole platform and its application to living cell imaging. Analyst 139:309–317

  33. 33.

    Ghosh T, Maiya BG, Wong MW (2004)) Fluoride ion receptors based on dipyrrolyl derivatives bearing electron-withdrawing groups: synthesis, optical and electrochemical sensing, and computational studies. J Phys Chem A 108:11249–11259

  34. 34.

    Rivadehi S, Reid EF, Hogan CF, Bhosale SV, Langford SJ (2012) Fluoride-selective optical sensor based on the dipyrrolyl-tetrathiafulvalene chromophore. Org Biomol Chem 10:705–709

  35. 35.

    Shahid M, Srivastava P, Misra A (2011) An efficient naphthalimide based fluorescent dyad (ANPI) for F and Hg 2+ mimicking OR, XNOR and INHIBIT logic functions. New J Chem 35:1690–1700

  36. 36.

    Bose P, Ahamed BN, Ghosh P (2011) Functionalized guanidinium chloride based colourimetric sensors for fluoride and acetate: single crystal X-ray structural evidence of-NH deprotonation and complexation. Org Biomol Chem 9:1972–1979

  37. 37.

    Zhou Y, Zhang JF, Yoon J (2014) Fluorescence and colorimetric chemosensors for fluoride-ion detection. Chem Rev 114:5511–5571

  38. 38.

    Iniya M, Jeyanthi D, Krishnaveni K, Chellappa D (2015) A bifunctional chromogenic and fluorogenic probe for F and Al3+ based on azo-benzimidazole conjugate. J Lumin 157:383–389

  39. 39.

    Pereira G, Castanheira EMS, Ferreira PMT, Queiroz MRP (2010) Synthesis and photophysical studies of new fluorescent indole derivatives obtained from β-bromodehydroamino acids–interaction with fluoride anions. Eur J Org Chem 464–475

  40. 40.

    Anand T, Sivaraman G, Iniya M, Siva A, Chellappa D (2015) Aminobenzohydrazide based colorimetric and ‘turn-on’ fluorescence chemosensor for selective recognition of fluoride. Anal Chim Acta 876:1–8

  41. 41.

    Jeong HY, Lee SY, Kim C (2017) Furan and julolidine-based “turn-on” fluorescence chemosensor for detection of F in a near-perfect aqueous solution. J Fluoresc 27:1457–1466

  42. 42.

    Kim M, Wiemer DF (2004) EDC-mediated condensations of 1-chloro-5- hydrazino-9, 10-anthracenedione, 1-hydrazino-9, 10-anthracenedione, and the corresponding anthrapyrazoles. Tetrahedron Lett 45:4977–4980

  43. 43.

    Yang X, Pan ZT, Ma Y (2003) Rhoda mine B as standard substance to measure the fluorescence-quantum yield. J Anal Sci 19:588–589 (in Chinese)

  44. 44.

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

  45. 45.

    Joshi BP, Park J, Lee WI, Lee KH (2009) Ratiometric and turn-on monitoring for heavy and transition metal ions in aqueous solution with a fluorescent peptide sensor. Talanta 78:903–909

  46. 46.

    Boiocchi M, Del Boca L, Gómez DE, Fabbrizzi L, Licchelli M, Monzani E (2004) Nature of urea-fluoride interaction: incipient and definitive proton transfer. J Am Chem Soc 126:16507–16514

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Acknowledgements

This study was supported by the Science Foundation for Creative Research Groups of HBNU (No. T201501) and Foundation for Hubei Key Laboratory of Pollutant Analysis and Reuse Technology (No. PA150204).

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Correspondence to Sheng-Li Hu.

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Hu, Y., Liu, Y., Li, Q. et al. New Colorimetric and Fluorometric Fluoride Ion Probe Based on Anthra[1,9-cd]pyrazol-6(2H)-one. J Fluoresc 27, 2287–2294 (2017). https://doi.org/10.1007/s10895-017-2170-7

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Keywords

  • Colorimetric
  • Fluorometric
  • Fluoride ion
  • Anthra[1,9-cd]pyrazol-6(2H)-one
  • Theoretical calculations