Compound and composition for detecting phosgene and diethyl chlorophosphate

• US 10,640,513 B2
• Filed: 02/23/2017
• Issued: 05/05/2020
• Est. Priority Date: 02/24/2016
• Status: Active Grant

• Current Assignee: EWHA University-Industry Collaboration Foundation (Ewha Womans University)
• Original Assignee: EWHA University-Industry Collaboration Foundation (Ewha Womans University)
• Inventors: Yoon, Juyoung, Zhou, Xin, Hu, Ying, Chen, Liyan
• Primary Examiner(s): Hixson, Christopher Adam
• Assistant Examiner(s): Berkeley, Emily R.
• Application Number:
  US15/440,748
• Publication Number:
  US 20170240557A1
• Time in Patent Office: Days
• Field of Search: 436 92
• CPC Class Codes: C07D 209/14 Radicals substituted by nitrogen atoms, not forming part of a nitro radical
• CPC Class Codes: C07D 221/14 Aza-phenalenes, e.g. 1,8-naphthalimide
• CPC Class Codes: C07D 271/12 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 311/88 Nitrogen atoms
• CPC Class Codes: C07D 491/107 with only one oxygen atom as ring hetero atom in the oxygen-containing ring
• CPC Class Codes: G01N 2021/7783 Transmission, loss
• CPC Class Codes: G01N 2021/7786 Fluorescence
• CPC Class Codes: G01N 31/223 for investigating presence of specific gases or aerosols G01N31/221, G01N31/222 take precedence; actuation of fire alarm by presence of smoke or gases G08B17/10

Abstract

The present invention relates to a compound for detecting phosgene and DCP (diethyl chlorophosphate) and a composition for detecting phosgene and DCP (diethyl chlorophosphate) comprising the said compound. More precisely, the compound for detecting phosgene and DCP of the present invention can selectively detect phosgene and DCP either in the liquid phase of gas phase by detecting the changes of fluorescence and color development very quickly within a few seconds with nM sensitivity. Therefore, the compound can also be effectively used as an ingredient for the composition and kit for the detection of one or more materials selected from the group consisting of phosgene and DCP.

Claims

1. A method for the detection of phosgene and/or diethyl chlorophosphate (DCP) comprising:

contacting a compound represented by formula 1 below with a sample to be analyzed; and

evaluating changes of fluorescence or absorption properties of the compound after contacting the compound with the sample;

2. The method according to claim 1, wherein R¹ is —

H, C1-5 straight or C3-5 branched alkyl, C1-5 straight or C3-5 branched alkoxy, or 4-6 membered heterocycloalkyl containing 2-3 hetero atoms selected from N, O, and S.

3. The method according to claim 1, wherein R¹ is C1-4 straight or C3-4 branched alkyl, or 6 membered heterocycloalkyl containing 2-3 hetero atoms selected from N, O, and S.

4. The method according to claim 1, wherein the compound represented by formula 1 above is the compound selected from the following compounds:

5. The method according to claim 1, wherein the compound is provided in a kit for the detection of phosgene and/or DCP.

6. The method according to claim 5, wherein the kit is capable of detecting changes of fluorescence or absorbance caused by the changes of -conjugation system of the compound, which results from nucleophilic attack of phenylenediamine included in the compound against phosgene or DCP.

7. The method of claim 1, wherein the method detects phosgene, and evaluating the fluorescence or absorption properties of the compound comprises detecting a yellow or purple fluorescence color in the presence of phosgene.

8. The method of claim 7, wherein the fluorescence color changes from yellow to a purple color as a concentration of phosgene increases.

9. The method of claim 1, wherein the method detects DCP, and evaluating the fluorescence or absorption properties of the compound comprises detecting a green fluorescence color in the presence of DCP.

10. The method of claim 9, wherein the green fluorescence color increases in intensity as a concentration of DCP increases.

11. The method of claim 1, wherein the method detects phosgene or DCP in a gas phase.

12. The method of claim 1, wherein the method detects phosgene or DCP in a liquid phase.

13. A method for the detection of phosgene and/or diethyl chlorophosphate (DCP), comprising:

contacting a gas or liquid sample to be analyzed with a compound selected from;

14. The method of claim 13, wherein the sample is a gas sample.