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Detection of low concentrations of volatile amines in aqueous solutions using pH-dependent fluorophores

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Abstract

The fluorescence of 2-haphthole (NL) and 1-naphthylamine (NA) has been studied depending on the concentration of amines: dimethylamine (DMA), trimethylamine (TMA), and pyridine (Pyr). The fluorescence spectrum of NL has two well-resolved bands with the maxima at 355 and 415 nm, corresponding to the protonated and deprotonated forms of 2-naphthole, the relative intensity of which depends on the concentration of aliphatic amines, but is essentially independent of the Pyr concentration. The parallel measurements of the pH of the medium showed that there is an unequivocal correlation between pH, ratio of intensities of two bands of the NL fluorescence, and concentration of aliphatic amines. It has been shown that NA has only one fluorescence band (447 nm); however, its intensity (quantum yield) is high and it is sensitive to the concentration of all three amines and pH. The pH-Metric titration of NA makes it possible to determine pK of protonation of this sensor and the pH value corresponding to the maximum slope of the titration curve, or to the maximum slope of the dependence of fluorescence intensity on the concentration of amine. This point (pH ≈ 4.2) is used as the initial one in the determination of low concentrations of amines. The effect of β-cyclodextrin (β-CD), crown ether 18-crown-6, and NA concentration on the NA sensitivity to the concentration of amines has been studied. The sensitivity of NA to Pyr is lower than to DMA, but higher than for TMA. In the presence of 2 mM of β-CD in the solution, the sensitivity of NA in relation to three amines is approximately similar.

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References

  1. W. L. Gong, K. J. Sears, J. E. Alleman, and E. R. Blatchley, “Toxicity of model aliphatic amines and their chlorinated forms,” Environ. Toxicol. Chem. 23(2), 239–244 (2004).

    Article  Google Scholar 

  2. B. Timmer, W. Olthuis, and A. van den Berg, “Ammonia sensors and their applications—a review,” Sensors Actuators B Chem. 107(2), 666–677 (2005).

    Article  Google Scholar 

  3. R. J. Shakila, K. Vijayalakshmi, and G. Jeyasekaran, “Changes in histamine and volatile amines in six commercially important species of fish of the Thoothukkudi coast of Tamil Nadu, India stored at ambient temperature,” Food Chem. 82(3), 347–352 (2003).

    Article  Google Scholar 

  4. G. Suzzi and F. Gardini, “Biogenic amines in dry fermented sausages: a review,” Int. J. Food Microbiol. 88(1), 41–54 (2003).

    Article  Google Scholar 

  5. A. D. Eaton, L. S. Clesceri, and A. E. Greenberg, Standard Methods for the Examination of Water and Wastewater (American Public Health Association, Association A.P.H., Association A.W.W., Federation W.E., 1995).

    Google Scholar 

  6. R. G. Compton and G. H. W. Sanders, Electrode Potentials (Oxford Univ. Press, 1996).

    Google Scholar 

  7. Z. Marczenko, Spectrophotometric Determination of Elements (E. Horwood, 1976).

    Google Scholar 

  8. H. Nanto, T. Minami, and S. Takata, “Zinc-oxide thin-film ammonia gas sensors with high-sensitivity and excellent selectivity,” J. Appl. Phys. 60(2), 482–484 (1986).

    Article  Google Scholar 

  9. G. S. T. Rao and D. T. Rao, “Gas sensitivity of ZnO based thick film sensor to NH3 at room temperature,” Sensors Actuators B. Chem. 55(2–3), 166–169 (1999).

    Article  Google Scholar 

  10. R. Sharma and A. A. Sagade, “Copper sulphide (CuxS) as an ammonia gas sensor working at room temperature,” Sensors Actuators B. Chem. 133(1), 135–143 (2008).

    Article  Google Scholar 

  11. J. M. Charlesworth and C. A. McDonald, “A fibreoptic fluorescing sensor for amine vapours,” Sensors and Actuators B. Chem. 8, 137–142 (1992).

    Article  Google Scholar 

  12. R. C. Weast, Handbook of Chemistry and Physics (CRC Press, Boca Raton, FL, 1978).

    Google Scholar 

  13. K. Waich, T. Mayr, and I. Klimant, “Fluorescence sensors for trace monitoring of dissolved ammonia,” Talanta 77, 66–72 (2008).

    Article  Google Scholar 

  14. D. Staneva, R. Betcheva, and J.-M. Chovelon, “Optical sensor for aliphatic amines based on the simultaneous colorimetric and fluorescence responses of smart textile,” J. Appl. Polymer Sci. 106, 1950–1956 (2007).

    Article  Google Scholar 

  15. K. Oberg, R. Hodyss, and J. L. Beauchamp, “Simple optical sensor for amine vapors based on dyed silica microspheres,” Sensors Actuators B. Chem. 115(1), 79–85 (2006).

    Article  Google Scholar 

  16. R. H. Yang, Wang KeMin, and D. Xiao, “A host-guest optical sensor for aliphatic amines based on lipophilic cyclodextrin,” Fresenius J. Anal. Chem. 367, 429–435 (2006).

    Article  Google Scholar 

  17. R. Waich, T. Mayr, and I. Klimant, “Microsensors for detection of ammonia at ppb-concentration levels,” Meas. Sci. Technol. 18, 3195–3201 (2007).

    Article  Google Scholar 

  18. Kim Ha, K. M. K. Na Swamy, and J. Yoon, “Study on various fluorescein derivatives as pH sensors,” Tetrahedron Lett. 52, 2340–2343 (2011).

    Article  Google Scholar 

  19. Ma Li-jun, W. Cao, J. Liu, D. Deng, Y. Wu, Y. Yan, and L. Yuhua Yang, “A highly selective and sensitive dualresponsive pH probe in water,” Sensors Actuators B. Chem. 169, 243–247 (2012).

    Article  Google Scholar 

  20. I. Suzuki, M. Ui, and A. Yamauchi, “Pyrene-appended alpha-cyclodextrin as a fluorescent probe responding to a wide range,” Anal. Sci. 23, 655–657 (2006).

    Article  Google Scholar 

  21. I. Oliveri and S. D. Di Bella, “Sensitive fluorescence detection and Lewis basicity of aliphatic amines,” J. Phys. Chem. A 115, 14325–14330 (2011).

    Article  Google Scholar 

  22. X. Zhang, X. Liu, R. Lu, H. Zhang, and P. Gong, “Fast detection of organic amine vapors based on fluorescent nanofibrils fabricated from triphenylamine functionalized beta-diketone-boron difluoride,” J. Mater. Chem. 22, 1167 (2012).

    Article  Google Scholar 

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Correspondence to B. B. Meshkov.

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Original Russian Text © B.B. Meshkov, I.V. Ionova, V.P. Tsybyshev, M.V. Alfimov, V.A. Livshits, 2015, published in Rossiiskie Nanotekhnologii, 2015, Vol. 10, Nos. 5–6.

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Meshkov, B.B., Ionova, I.V., Tsybyshev, V.P. et al. Detection of low concentrations of volatile amines in aqueous solutions using pH-dependent fluorophores. Nanotechnol Russia 10, 337–344 (2015). https://doi.org/10.1134/S199507801503012X

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