Fluorescent compositions

Patent metadata

Field	Value
Publication number	US-11680202-B2
Application number	US-202117381412-A
Country	US
Kind code	B2
Filing date	Jul 21, 2021
Priority date	Feb 19, 2018
Publication date	Jun 20, 2023
Grant date	Jun 20, 2023

Abstract

An article that includes a fluorescent composition having at least one of a fluorescent sensor compound and organic reporter molecules encapsulated in a microsphere structure. When encapsulated, the fluorescent sensor compound and the organic reporter molecules are distributed in a liquid organic matrix. When non-encapsulated, the remaining one of the fluorescent sensor compound and the organic reporter molecules reside in the matrix. In response to a force applied to the composition sufficient to break at least a portion of the microsphere structure, the fluorescent sensor compound and the organic reporter molecules are transformed into a non-reversible fluorescent state exhibiting a quantum yield greater than 0.2. The fluorescent state is objectively visually verifiable without physically contacting the composition.

First claim

What is claimed is:

1. A detection method, comprising:
combining a material and a substrate to form an article;
wherein the material comprises:
at least one of a fluorescent sensor compound and organic reporter molecules encapsulated in a microsphere structure;
wherein when encapsulated, the fluorescent sensor compound and the organic reporter molecules are distributed in a liquid organic matrix;
wherein when non-encapsulated, the remaining one of the fluorescent sensor compound and the organic reporter molecules reside in the matrix;

applying a force to the material sufficient to break at least a portion of the microsphere structure to transform the fluorescent sensor compound and the organic reporter molecules into a non-reversible fluorescent state exhibiting a quantum yield greater than 0.2; and
visually verifying the fluorescent state without physically contacting the material.

2. The method of claim 1 , wherein the substrate and material are combined by coating the material onto the substrate.

3. The method of claim 1 , wherein the article is formed by an additive manufacturing technique.

4. The method of claim 1 , wherein the substrate is an exterior surface of a container.

5. The method of claim 1 , wherein the substrate and material are combined by incorporating the material into a base material of a container prior to formation of the container.

6. The method of claim 5 , wherein incorporating the material into the base material is achieved by the method selected from a group consisting of at least one of 3-D printing, casting, molding, spraying, or a combination thereof.

7. The method of claim 1 , wherein the fluorescent state is achieved as a result of a turn-on fluorescence response accomplished with the fluorescent sensor mixing or in mass transport with the organic reporter molecules contained in the liquid organic matrix according to strategies comprising: an ion-induced conformational change, a change in pH, a Förster Resonance Energy Transfer, a charge-transfer complex formation, and combinations thereof.

8. The method of claim 7 , wherein the ion-induced conformational change strategy involves binding of a metal ion to at least one of oxygen and nitrogen atoms of the fluorescent sensor compound.

9. The method of claim 8 , wherein the metal ion includes at least one of Fe 3+ , Cu 2+ , and Zn 2+ .

10. The method of claim 7 , wherein the fluorescent sensor compound is selected from the group consisting of fluorophores based on spirolactam, rhodamine, coumarin, acridine, phenanthrene, eosin, quinoline, anthracene groups, and combinations thereof.

11. The method of claim 7 , wherein the charge-transfer complex formation charge-transfer strategy is achieved by the fluorescent sensor compound being responsive to electron-donating or electron-withdrawing components.

12. The method of claim 11 , wherein the charge transfer complex formation includes electron-donating or electron-withdrawing components selected from the group consisting of amines and nitro-groups.

13. The method of claim 7 , wherein the ion-induced conformational change involves the fluorescent sensor compound being responsive to a surfactant.

14. The method of claim 13 , wherein the surfactant is sodium dodecylsulfate.

15. The method of claim 7 , wherein the change in pH strategy includes organic reporter molecules selected from the group consisting of coumarins, imadozopyridinium compounds, carboxynaphthofluorescein, aminoacridine hydrochloride, ammonium naphthalenesulfonic acid, hydroxyl quinolones, sodium pyrenesulfonic acids, Rhodamine esters, and combinations thereof.

16. The method of claim 7 , wherein the Förster Resonance Energy Transfer strategy includes a short-wavelength emitting fluorescent donor microencapsulated in a polymer or silica shell paired with an acceptor fluorophore residing in the liquid organic matrix or in separate microcapsules.

17. The method of claim 16 , wherein pairs of microencapsulated fluorescent donors/acceptor fluorophores are selected from the group consisting of biphenyl/pyrene, 2,5-diphenyloxazole/rhodamine 6G, and naphthalene/coumarin 540A.

18. The method of claim 7 , wherein the charge transfer compound formation strategy includes a charge transfer complex formed between anthracene and N,N-diethylaniline that exhibits a red-shift in the emission spectrum following mixing.

Assignees

• Nat Tech & Eng Solutions Sandia Llc

Inventors

• Smartt Heidi A
• Blair Dianna S
• Romero Juan A
• Feng Patrick L

Classifications

• C09B6/00

  Anthracene dyes not provided for above · CPC title

• C09K11/54

  containing zinc or cadmium · CPC title

• B33Y10/00

  Processes of additive manufacturing · CPC title

• C09B57/02

  Coumarine dyes · CPC title

• C09K11/07 Primary

  having chemically-interreactive components, e.g. reactive chemiluminescent compositions · CPC title