Color matched and bright fluorescent materials composed of small-molecule ionic lattices

Patent metadata

Field	Value
Publication number	US-12415927-B2
Application number	US-201916762628-A
Country	US
Kind code	B2
Filing date	Mar 10, 2019
Priority date	Mar 10, 2018
Publication date	Sep 16, 2025
Grant date	Sep 16, 2025

Abstract

The present disclosure concerns the design, formulations, preparations and optical properties of compounds of Formulas (I) and (VI):

(charged dye m+ ) x ·(counterion n− ) y ·(counterion receptor) z   (I) and

(charged dye m− ) x ·(counterion n+ ) y ·(counterion receptor) z   (VI).

The charged dye m+ is a cationic dye, counterion n− is an anion, and counterion receptor is a binding ligand for the counterion n− , wherein m, n, x and y are integers greater than or equal to 1, and products of x·n and m·y are identical for formula (I).
The charged dye m− is a anionic dye, counterion n+ is a cation, and counterion receptor is a binding ligand for the counterion n+ , wherein m, n, x and y are integers greater than or equal to 1, and products of x·n and m·y are identical for formula (VI).

First claim

What is claimed is:

1. A solid state, ionic lattice of Formula (I):
(charged dye m+ ) x ·(counterion n− ) y ·(heteromacrocycle counterion receptor) z   (I),

wherein charged dye n+ is a cationic dye, counterion n− is an anion, and heteromacrocycle counterion receptor is a binding ligand for counterion n− ,
wherein m, n, x, y, and z are integers greater than or equal to 1 and products of x·n and m·y are identical,
wherein the cationic dye comprises a light-absorbing unit or both a light-absorbing unit and a light emissive unit,
wherein the cationic dye in the solid state, ionic lattice is electronically isolated, and
wherein the heteromacrocycle counterion receptor is Formula (IV):

wherein R 1 , R 2 , R 3 , R 4 , and R 5 of Formula (IV) are identical and are selected from a group consisting of alkyl, alkyl-substituted phenyl derivatives, and substituted glycol derivatives, alkenyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR 6 , —N(R 7 R 11 ), —CO 2 R 9 , —C(O)—N(R 10 R 11 ), wherein R 6 , R 7 , R 11 , R 9 , R 10 , and R 11 are each selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NHalkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen, or a combination thereof.

2. The solid state, ionic lattice of claim 1 , wherein the cationic dye is selected from the group consisting of the following members:

3. The solid state, ionic lattice according to claim 1 , wherein the anion is selected from the group consisting of BF 4 − , ClO 4 − , PF 6 − , N(SO 2 CF 3 ) 2 − , N(SO 2 C 2 F 5 ) 2 − , CH 3 SO 3 − , CF 3 SO 3 − , AsO 4 3− , HAsO 4 2− , H 2 AsO 4 − , AsF 6 − , AlCl 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , SO 4 2− , HSO 4 − , Cl − , Br − , I − , cyanide, BrO 4 − , IO 4 − , F − , HF 2 − , TcO 4 − , SCN − , N 3 − , I 3 − , CO 3 2− , HCO 3 − , P 2 O 7 4− , HP 2 O 7 3− , H 2 P 2 O 7 2− , and H 3 P 2 O 7 − .

4. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is Formula (I-1):

5. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

6. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

7. The compound according to claim 1 , wherein the cationic dye comprises a light-absorbing unit and a light emissive unit.

8. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

9. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

10. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

11. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

12. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

13. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

14. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

15. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

16. The solid state, ionic lattice according to claim 1 , wherein Formula (I) is

17. A formulation comprising a solid state, ionic lattice of claim 1 .

18. The formulation according to claim 17 , wherein the formulation comprises a solid state material.

19. The formulation according to claim 18 , wherein the solid state material is selected from the group consisting of a powder, amorphous solid, thin films, crystals, microparticles, polymer composites, nanoparticles, colloid of microparticles, and nanoparticles.

20. The formulation according to claim 17 , wherein the formulation is prepared from a solution, a powder or a colloid.

21. The formulation according to claim 18 , wherein the formulation comprises a colloid.

22. A method of producing a material, comprising:
preparing a first mixture comprising the solid state, ionic lattice according to claim 1 ; and
condensing the first mixture to form a material in a solid state.

23. A method of detecting a substance, comprising:
contacting the substance with a solid state, ionic lattice according to claim 1 to form a mixture; and
measuring a change in at least one spectral property in the solid state, ionic lattice of the mixture as a result of the contacting step relative to the substance alone or the solid state, ionic lattice alone,
wherein the substance is detected by the change in at least one spectral property in the solid state, ionic lattice as a result of the measuring step with the mixture.

24. A method of adding light absorption or both light absorption and emission to a polymer, comprising:
providing the polymer; and
contacting the polymer with a SMILES material comprising a solid state, ionic lattice according to claim 1 .

25. A method of staining a biological material, comprising:
providing the biological material; and
contacting the biological material with microparticles or nanoparticles comprising a SMILES material comprising a solid state, ionic lattice according to claim 1 .

26. A method of increasing the photostability of an ionic dye, comprising:
providing the ionic dye; and
converting the ionic dye into a SMILES material comprising a solid state, ionic lattice according to claim 1 .

27. A method of increasing the solubility and mixability of an ionic dye with polymers and non-polar solvents, comprising:
providing the ionic dye; and
converting the ionic dye into a SMILES material comprising a solid state, ionic lattice according to claim 1 .

28. A method of generating a SMILES material with a programmable light absorption or both light absorption and emission properties, comprising:
providing an ionic dye, wherein ionic dye comprises specific light absorption properties; and
converting the ionic dye into the SMILES material comprising a solid state, ionic lattice according to claim 1 .

Assignees

• Univ Indiana Res & Tech Corp
• Univ Copenhagen

Inventors

• Flood Amar H
• Laursen Bo Wegge

Classifications

• C09B69/065

  of cationic azo dyes · CPC title

• C09B69/06 Primary

  of cationic dyes with organic acids {or with inorganic complex acids} · CPC title

• C09B69/04

  of anionic dyes with nitrogen containing compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K11/02

  Use of particular materials as binders, particle coatings or suspension media therefor · CPC title