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Europium Tetrakis Dibenzoylmethide Triethylammonium: Synthesis, Additives, and Applications

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Triboluminescence

Abstract

There are a number of techniques currently being used for damage detection and monitoring of civil, aerospace, and military structures and aircraft. However, the major drawbacks of the current techniques are that they do not provide in situ and distributed sensing. Wiedemann and Schmidt defined triboluminescence (TL) as the emission of light produced by mechanical action. In recent years, triboluminescent materials have been proposed for use as the active element in smart structural sensors. To sense damage, these materials would be embedded into the structure. If damage occurs to this structure, the embedded triboluminescent material would give off visible light. This light could be transferred by lightweight fiber optics or wireless detector to a computer-based detection system to warn occupants in real time that a significant impact event has occurred. In addition, the triboluminescent based sensor could allow for real-time monitoring of both the magnitude and location of damage to the host structure. One of the brightest triboluminescent materials currently known is europium tetrakis dibenzoylmethide triethylammonium (EuD4TEA). This research delved into the feasibility of enhancing the properties of EuD4TEA by (a) modifying the synthesis process and (b) determining the reproducibility of the synthetic procedure by measuring the batch variation error. Further, the study evaluated the possible techniques that can be incorporated in to the synthesis technique to enhance the TL by (a) introducing various inorganic and organic dopants; (b) optimizing dopant concentration; (c) studying solvents effects on TL; and (d) evaluating the effects of ionizing radiation on TL. In addition, the research discusses in depth the experimental development of a simple apparatus for the measurement of TL in the laboratory by using a twofold technique consisting of measuring the triboluminecent  intensity and/or spectral characterization. This enabled for the determination of a unique decay time for a particular compound. In addition, impact studies have been conducted to correlate the impact energy (velocity) with triboluminescent emission, thus allowing a system to detect and evaluate the magnitude of the impacts. The spectra of these compounds have been analyzed in detail to investigate the cause of luminescence and designate the transitional energy levels for each of the peaks. Finally in order to study the feasibility for structural and/or sensor application, the effect of introducing EuD4TEA into poly(methyl methacrylate) and its impact on the TL emission spectra are determined.

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Author information

Authors and Affiliations

  1. Carderock Division, Naval Surface Warfare Center, Code 632, West Bethesda, 20817, USA

    Ross S. Fontenot

  2. Department of Physics, Chemistry, and Mathematics, Alabama A&M University, 1268, Normal, AL, 35762, USA

    Kamala N. Bhat & Mohan D. Aggarwal

  3. Department of Physics, University of Louisiana, 44210, Lafayette, LA, 70504, USA

    William A. Hollerman

Authors
  1. Ross S. Fontenot
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  2. Kamala N. Bhat
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  3. William A. Hollerman
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  4. Mohan D. Aggarwal
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Corresponding author

Correspondence to Ross S. Fontenot .

Editor information

Editors and Affiliations

  1. Industrial & Manufacturing Engineering Department, FAMU-FSU College of Engineering, Tallahassee, Florida, USA

    David O. Olawale

  2. Industrial & Manufacturing Engineering Department, FAMU-FSU College of Engineering, Tallahassee, Florida, USA

    Okenwa O. I. Okoli

  3. Naval Surface Warfare Center, Bethesda, Maryland, USA

    Ross S. Fontenot

  4. Dept of Physics, University of Louisiana, Lafayette, Louisiana, USA

    William A. Hollerman

Appendices

Appendix 1: Synthesizing EUD4TEA

The materials required to synthesize EuD4TEA include the following:

  1. 1.

    Europium (III) nitrate hydrate, powder, 99.999 % (Metall Rare Earth Limited, 6371).

  2. 2.

    1,3-diphenyl-1,3-propanedione (dibenzoylmethane), powder, 98 % (Sigma-Aldrich, D33454).

  3. 3.

    Triethylamine (TEA), liquid, ≥99.5 % (Sigma-Aldrich, 471283).

  4. 4.

    25 mL of solvent.

    1. (a)

      Ethanol, 200 proof, anhydrous, ≥99.5 % (Sigma-Aldrich, 459836).

    2. (b)

      Ethyl alcohol, denatured (Fisher Scientific, A407).

    3. (c)

      Acetone, laboratory reagent, ≥99.5 % (Sigma-Aldrich, 179973).

    4. (d)

      Methanol, anhydrous (Sigma-Aldrich, 322415).

    5. (e)

      Ethyl alcohol, denatured laboratory grade, 95 % (Scholar Chemistry, 9506406).

  5. 5.

    125 mL Erlenmeyer flask.

  6. 6.

    Whatman ashless, grade 42 filter paper, 125 mm diameter (Sigma-Aldrich, Z241113).

  7. 7.

    Powder funnel, polypropylene, 100 mm diameter (Ward Scientific, 6187107).

  8. 8.

    Hot plate.

  9. 9.

    Storage container, 1 oz clear round wide mouth jars (Uline, S-14487).

The common manufacturers for making EuD4TEA described in this chapter are listed . It should be noted that other manufacturers could be used as long as the purity is similar. The user must be careful, however, when using solvents. While most solvents are similar between manufacturers, denatured ethyl alcohol varies greatly. For example, using the Fisher brand denatured ethyl alcohol will yield similar results to the pure ethyl alcohol, acetone, and methanol. However, the Scholar Chemistry version will not yield similar results. These variations were observed in both the denatured and denatured anhydrous versions of ethyl alcohol. As a result, it is imperative that one solvent be used throughout the same experimental run in order to do batch comparison.

The steps to synthesize EuD4TEA are as follows:

  1. 1.

    Set the hot plate to a low heat, between 2 and 3, under a vent hood.

  2. 2.

    Transfer 25 mL of the desired solvent to an Erlenmeyer flask.

  3. 3.

    Place the Erlenmeyer flask on the hot plate.

  4. 4.

    Add 4 mmol (1.44 g) of europium nitrate to the solvent.

  5. 5.

    Add 13 mmol (2.93 g) of DBM to the solution.

  6. 6.

    Place a funnel on top of the Erlenmeyer flask to prevent solvent loss by evaporation.

  7. 7.

    Mix the slurry over a hot plate until completely dissolved.

  8. 8.

    Remove from the hot plate.

  9. 9.

    Add 14 mmol (2 mL) of TEA to the solution.

  10. 10.

    Place a paper towel over the Erlenmeyer flask to ensure that nothing is added while crystallizing.

  11. 11.

    Set aside to cool overnight.

  12. 12.

    Once precipitation is complete, fold the filter paper in half twice.

  13. 13.

    Make a funnel out of the filter paper and place it inside a funnel.

  14. 14.

    Swirl the solution inside the Erlenmeyer flask so that the crystals break free from the Erlenmeyer flask.

  15. 15.

    Pour the solution into the funnel.

  16. 16.

    Let the solution pass through the paper so that only the crystals remain.

  17. 17.

    Repeat steps 12–14 until all the crystals have been transferred to the beaker into the filter paper.

  18. 18.

    Let dry for a few days.

  19. 19.

    Once dry, transfer to a container for storage.

Dopants can enhance the luminescence of many compounds. Depending on the type of dopant, a new synthesis procedure is required. For compound dopants such as caffeine or DMMP, the synthesis method is modified slightly. Step five above is replaced with add the required amount of dopant. The rest of the synthesis process remains unchanged. If the results from the added dopant does not take the shape of a Gaussian curve or the data is scattered, then the solution must be heated. It has been found that in the case of elemental dopants such as dysprosium, samarium, or uranium requires heating. The steps to synthesize EuD4TEA doped with elements are as follows:

  1. 1.

    Set the hot plate to 250 °C under a vent hood.

  2. 2.

    Set the stirrer to maximum.

  3. 3.

    Add 75 mL of the desired solvent to the Erlenmeyer flask.

  4. 4.

    Place the Erlenmeyer flask on the hot plate.

  5. 5.

    Add 4 mmol (1.44 g) of europium nitrate to the solution.

  6. 6.

    Add the desired amount of dopant.

  7. 7.

    Add 13 mmol (2.93 g) of DBM to the solution.

  8. 8.

    Place a funnel upside down on top of the Erlenmeyer flask to ensure that most of the solvent does not evaporate completely.

  9. 9.

    Let mix for 20 min.

  10. 10.

    Remove from the hot plate.

  11. 11.

    Remove the stirrer.

  12. 12.

    Add 14 mmol (2 mL) of TEA to the solution.

  13. 13.

    Place a paper towel over the many Erlenmeyer flask to ensure that nothing is added while crystallizing.

  14. 14.

    Set aside to cool overnight.

  15. 15.

    Once precipitation is complete, fold the filter paper in half twice.

  16. 16.

    Make a funnel out of the filter paper and place it inside a funnel.

  17. 17.

    Swirl the solution inside the Erlenmeyer flask so that the crystals break free from the Erlenmeyer flask.

  18. 18.

    Pour the solution into the funnel.

  19. 19.

    Let the solution pass through the paper so that only the crystals remain.

  20. 20.

    Repeat steps 12–14 until all the crystals have been transferred to the Erlenmeyer flask into the filter paper.

  21. 21.

    Let dry for a few days.

  22. 22.

    Once dry, transfer to a many container for storage.

Appendix 2: Directions for Drop Tower

The directions on how to perform the drop tower test are as follows:

  1. 1.

    Get a new Plexiglas.

  2. 2.

    Set the Photodiode 2.25 cm away from the bottom of the Plexiglas.

  3. 3.

    Set the Amplifier to the appropriate settings (200 μA for ZnS:Mn and EuD4TEA).

  4. 4.

    Place 1.068 ± 0.005 g of material in the center of the drop tower.

  5. 5.

    Place the pin and ball 42 in. from the sample.

  6. 6.

    Set the oscilloscope to the required settings.

    1. (a)

      Channel 1: 2.00 V (varies between materials).

    2. (b)

      M Time Scale = 500 μs (EuD4TEA), 250 μs (ZnS:Mn).

    3. (c)

      Center Position M = 780 μs.

    4. (d)

      CH 1 trigger ʃ = 80 mV

    5. (e)

      Probe attenuation = 20×

  7. 7.

    Release the ball (130.276 g).

  8. 8.

    Save the light duration and repeat until you have five good data sets.

  9. 9.

    Clean out the drop tower and place the powder and Plexiglas into a storage bag making the date, material, and number of drops.

  10. 10.

    Copy the data to the computer.

  11. 11.

    Run the Area under curves2 LabVIEW program to determine the light yield.

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Fontenot, R.S., Bhat, K.N., Hollerman, W.A., Aggarwal, M.D. (2016). Europium Tetrakis Dibenzoylmethide Triethylammonium: Synthesis, Additives, and Applications. In: Olawale, D., Okoli, O., Fontenot, R., Hollerman, W. (eds) Triboluminescence. Springer, Cham. https://doi.org/10.1007/978-3-319-38842-7_7

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