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US-12625077-B2 - Fluorosurfactant detection

US12625077B2US 12625077 B2US12625077 B2US 12625077B2US-12625077-B2

Abstract

A method may comprise: exposing a substituted chromone dissolved in a solvent to a sample; taking a fluorescence measurement of the sample after exposure to the substituted chromone; and determining a presence or absence of one or more ions in the sample, a concentration of the one or more ions in the sample, or both based on the fluorescence measurement.

Inventors

  • Jake R. ZIMMERMAN

Assignees

  • OHIO NORTHERN UNIVERSITY

Dates

Publication Date
20260512
Application Date
20210813

Claims (20)

  1. 1 . A method comprising: exposing a substituted chromone according to Compound 1 to a sample, wherein R 1 is methyl acetate, methoxy, or methyl (2,2-dimethyl) acetate, R 2 is 4-methylbenzoyl, 4-methoxybenzoyl, naphthalene-1-carbonyl, naphthalene-2-carbonyl, 4-phenylbenzoyl, or a perfluoroalkyl sulfonic acid compound wherein the alkyl is C 5 -C 12 , R 3 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, R 4 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, R 5 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, and R 6a-e are any of hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, taking a fluorescence measurement of the sample after exposure to the substituted chromone; and determining a presence or absence of one or more per- or polyfluoroalkyl hydrocarbons (PFAS), a concentration of the one or more PFAS in the sample, or both based on the fluorescence measurement.
  2. 2 . The method of claim 1 , wherein Compound 1 is dissolved in a solvent.
  3. 3 . The method of claim 1 , wherein Compound 1 is disposed on a test strip.
  4. 4 . The method of claim 1 , wherein the fluorescence measurement is a first fluorescence measurement; wherein the method further comprises taking a second fluorescence measurement of the sample occurs before exposing the substituted chromone; and wherein determining the presence or absence of the one or more PFAS in the sample, the concentration of the one or more PFAS in the sample, or both based on a comparison of the first and second fluorescence measurements.
  5. 5 . The method of claim 1 , wherein taking the fluorescence measurement of the sample involves exposing the sample to a 365 nm wavelength source and visually inspecting fluorescence from the sample.
  6. 6 . The method of claim 1 , wherein determining the presence or absence of the one or more PFAS in the sample, the concentration of the one or more PFAS in the sample, or both is based on a comparison of the fluorescence measurement and a color chart reference.
  7. 7 . The method of claim 1 , wherein the one or more PFAS comprise one or more selected from the group consisting of: perfluorooctanoic acid, perfluoroheptanoic acid, perfluoropentanoic acid, perfluorobutyric acid, perfluoropropionic acid, perfluorobutyric sulfonic acid, perfluorooctanesulfonyl chloride, undecafluoro-2-methyl-3-oxahexanoic acid, and any combination thereof.
  8. 8 . The method of claim 1 , wherein the sample is from drinking water; ground water; or a waste water effluent from a chemical, manufacturing, or nuclear plant.
  9. 9 . The method of claim 1 , wherein the sample is an extract from a soil sample.
  10. 10 . The method of claim 1 , wherein Compound 1 is
  11. 11 . The method of claim 1 , wherein Compound 1 is
  12. 12 . The method of claim 1 , wherein Compound 1 is
  13. 13 . The method of claim 1 , wherein Compound 1 is
  14. 14 . A method comprising: exposing a substituted chromone according to Compound 2 to a sample, wherein R 1 is methyl acetate, methoxy, or methyl (2,2-dimethyl) acetate, R 2 is 4-methylbenzoyl, 4-methoxybenzoyl, naphthalene-1-carbonyl, naphthalene-2-carbonyl, 4-phenylbenzoyl, or a perfluoroalkyl sulfonic acid compound wherein the alkyl is C 5 -C 12 , R 3 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, R 4 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, R 5 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, and R 6a-e are any of hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, taking a fluorescence measurement of the sample after exposure to the substituted chromone; and determining a presence or absence of one or more per- or polyfluoroalkyl hydrocarbons (PFAS), a concentration of the one or more PFAS in the sample, or both based on the fluorescence measurement.
  15. 15 . The method of claim 14 , wherein Compound 2 is dissolved in a solvent.
  16. 16 . The method of claim 14 , wherein Compound 2 is disposed on a test strip.
  17. 17 . The method of claim 14 , wherein the fluorescence measurement is a first fluorescence measurement; wherein the method further comprises taking a second fluorescence measurement of the sample occurs before exposing the substituted chromone; and wherein determining the presence or absence of the one or more PFAS in the sample, the concentration of the one or more PFAS in the sample, or both based on a comparison of the first and second fluorescence measurements.
  18. 18 . The method of claim 14 , wherein taking the fluorescence measurement of the sample involves exposing the sample to a 365 nm wavelength source and visually inspecting fluorescence from the sample.
  19. 19 . The method of claim 14 , wherein determining the presence or absence of the one or more PFAS in the sample, the concentration of the one or more PFAS in the sample, or both is based on a comparison of the fluorescence measurement and a color chart reference.
  20. 20 . The method of 14 , wherein the one or more PFAS comprise one or more selected from the group consisting of: perfluorooctanoic acid, perfluoroheptanoic acid, perfluoropentanoic acid, perfluorobutyric acid, perfluoropropionic acid, perfluorobutyric sulfonic acid, perfluorooctanesulfonyl chloride, undecafluoro-2-methyl-3-oxahexanoic acid, and any combination thereof.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS The present invention is a national stage application of pending International Patent Application No. PCT/US2021/045925 filed Aug. 13, 2021, which claims the benefit of U.S. Provisional Patent Application No. 62/706,413 filed Aug. 14, 2020, which are incorporated by reference herein in their entirety. FIELD OF THE INVENTION This invention relates to a new class of fluorophores that, in some instances, shifts emission wavelength upon interaction of per- and poly-fluoroalkyl substances (PFASs). The fluorophores are useful for, for example, detecting the presence of PFASs in field samples. BACKGROUND Once heralded as wonder chemicals, PFASs are now better known for their persistence in the environment and their bioaccumulation, contaminating water and soil and subsequently exerting toxic effects. The extent of PFAS contamination is currently unknown, and clean-up efforts are hampered because of the difficulty in detecting the compositions. Currently, samples must be removed from the site and sent to laboratories with sophisticated instrumentation to determine the presence of PFASs. Thus, a test for PFASs that is faster and less expensive is sought after, particularly a test that could be used in the field. BRIEF SUMMARY In some instances, a method of detecting PFASs may comprise exposing a substituted chromone according to Compound 1 to a sample. Subsequently, the method comprises taking a fluorescence measurement of the sample after exposure to the substituted chromone and determining a presence or absence of one or more per- or polyfluoroalkyl hydrocarbons (PFAS), a concentration of the one or more PFAS in the sample, or both based on the fluorescence measurement. R1 of Compound 1 is methyl acetate, methoxy, or methyl (2,2-dimethyl) acetate. R2 is 4-methylbenzoyl, 4-methoxybenzoyl, naphthalene-1-carbonyl, naphthalene-2-carbonyl, 4-phenylbenzoyl, or a perfluoroalkyl sulfonic acid compound wherein the alkyl is C5-C12. R3 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl; R4 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R5 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R6a-e are any of hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. In some instances, a method of detecting PFASs may comprise exposing a substituted chromone according to Compound 2 to a sample. Subsequently, the method comprises taking a fluorescence measurement of the sample after exposure to the substituted chromone and determining a presence or absence of one or more per- or polyfluoroalkyl hydrocarbons (PFAS), a concentration of the one or more PFAS in the sample, or both based on the fluorescence measurement. R1 of Compound 2 is methyl acetate, methoxy, or methyl (2,2-dimethyl) acetate. R2 is 4-methylbenzoyl, 4-methoxybenzoyl, naphthalene-1-carbonyl, naphthalene-2-carbonyl, 4-phenylbenzoyl, or a perfluoroalkyl sulfonic acid compound wherein the alkyl is C5-C12, R3 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, R4 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl, R5 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R6a-e are any of hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. In some instances, a method of detecting PFASs may comprise exposing a substituted chromone according to Compound 3 to a sample, taking a fluorescence measurement of the sample after exposure to the substituted chromone, and determining a presence or absence of one or more per- or polyfluoroalkyl hydrocarbons (PFAS), a concentration of the one or more PFAS in the sample, or both based on the fluorescence measurement. R1 is methyl acetate, methoxy, or methyl (2,2-dimethyl) acetate. R2 is 4-methylbenzoyl, 4-methoxybenzoyl, naphthalene-1-carbonyl, naphthalene-2-carbonyl, 4-phenylbenzoyl, or a perfluoroalkyl sulfonic acid compound wherein the alkyl is C5-C12. R3 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R4 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R5 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R6a-e are any of hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. In some instances, a PFAS detecting composition may comprise Compound 1, above, where R1 is methyl acetate, methoxy or methyl (2,2-dimethyl) acetate. R2 is 4-methylbenzoyl, 4-methoxybenzoyl, naphthalene-1-carbonyl, 4-phenylbenzoyl, a perfluoroalkyl sulfonic acid compound wherein the alkyl is C5-C12. R3 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R4 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R5 is hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. R6a-e is any of hydrogen, methoxy, bromo, chloro, fluoro, methyl, ethyl, or isopropyl. BRIEF DESCRIPTION OF THE FIGURES FIG. 1 illustrates an inve