IP Library Granted Patent US 10,538,701
Granted Patent B1
US 10,538,701 · App. 15/898,906 · Granted Jan 21, 2020

Fluorescent compositions

Inventors: Heidi A. Smartt (Albuquerque, NM); Dianna S. Blair (Albuquerque, NM); Juan A. Romero (Bayfield, CO); Patrick L. Feng (Livermore, CA)
Assignee: National Technology & Engineering Solutions of Sandia, LLC
C09K11/07C09K11/54C09K11/58C09K11/60B33Y10/00C07D311/82C09B6/00C09B15/00C09B57/02C09B57/14
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Quick Facts
Patent No.
US 10,538,701
App. No.
15/898,906
Granted
Jan 21, 2020
Kind
B1
Abstract

A fluorescent composition includes 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.

Claims (20)

1. A fluorescent composition comprising:

microspheres encapsulating at least one component selected from a group consisting of a fluorescent sensor compound and organic reporter molecules;

wherein the microspheres are distributed in a liquid organic matrix; and

wherein when either the fluorescent sensor compound or the organic reporter molecules component is non-encapsulated, the non-encapsulated component resides in the liquid organic matrix; and

wherein in response to a force applied to the composition sufficient to break at least a portion of the microspheres, 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;

wherein the fluorescent state is objectively visually verifiable without physically contacting the composition; and

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.

2. The composition of claim 1 , 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.

3. The composition of claim 1 , wherein the charge-transfer complex formation strategy is achieved by the fluorescent sensor compound being responsive to electron-donating or electron-withdrawing components.

4. The composition of claim 3 , wherein the electron-donating or electron-withdrawing components include amines and nitro-groups.

5. The composition of claim 1 , wherein the ion-induced conformational change involves the fluorescent sensor compound being responsive to a surfactant.

6. The composition of claim 1 , 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.

7. The composition of claim 1 , wherein the Förster Resonance Energy Transfer strategy includes one wherein the fluorescent sensor compound is a short-wavelength emitting fluorescent donor and wherein the microspheres are polymer or silica shells and wherein the organic reporter molecules are an acceptor fluorophore residing in the liquid organic matrix or in microspheres.

8. The composition of claim 7 , wherein pairs of microencapsulated fluorescent donors/acceptor fluorphores are selected from the group consisting of biphenyl/pyrene, 2,5-diphenyloxazole/rhodamine 6G, and naphthalene/coumarin 540A.

9. The composition of claim 1 , wherein the charge-transfer complex 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.

10. An article comprising:

a substrate and a coating comprising the composition of claim 1 applied over the substrate.

11. An article comprising:

a base material combined with the composition of claim 1 to form the article.

12. The article of claim 11 , wherein the article is formed by an additive manufacturing technique.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2018
From: SMARTT, HEIDI A.; BLAIR, DIANNA S.; ROMERO, JUAN A.; FENG, PATRICK L.
To: NATIONAL TECHNOLOGY & ENGINEERING SOLUTIONS OF SANDIA, LLC
Reel/Frame 045767/0405 →
CONFIRMATORY LICENSE Recorded Apr 10, 2018
From: NATIONAL TECHNOLOGY & ENGINEERING SOLUTIONS OF SANDIA, LLC
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 045879/0669 →