Water soluble fluorescent or colored dyes and methods for their use

Patent metadata

Field	Value
Publication number	US-11939474-B2
Application number	US-202217869366-A
Country	US
Kind code	B2
Filing date	Jul 20, 2022
Priority date	Aug 22, 2013
Publication date	Mar 26, 2024
Grant date	Mar 26, 2024

Abstract

Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I):

including stereoisomers, salts and tautomers thereof, wherein R 1 , R 2 , R 3 , L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , M 1 , M 2 , A, q, w and n are as defined herein. Methods associated with preparation and use of such compounds are also provided.

First claim

What is claimed is:

1. A compound having the following structure (Ig):

wherein:
M 1 is a moiety comprising three or more aryl or heteroaryl rings, or combinations thereof;
R 1 is H, an unsubstituted C 1 -C 6 alkyl or an unsubstituted alkoxy;
R 2 is cyanoalkyl;
R 3 is H or —Oaralkyl;
R 6 is an unsubstituted C 1 -C 6 alkyl;
R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are, at each occurrence, independently H; and
x, y and z are, at each occurrence, independently an integer from 1 to 5.

2. The compound of claim 1 , wherein each R 6 is isopropyl.

3. The compound of claim 1 , wherein R 2 is 2-cyanoethyl.

4. The compound of claim 1 , wherein R 3 is —ODMT.

5. The compound of claim 1 , wherein x, y and z are each 1.

6. The compound of claim 1 , wherein M 1 is a moiety comprising four or more aryl or heteroaryl rings, or combinations thereof.

7. The compound of claim 1 , wherein M 1 is fluorescent or colored.

8. The compound of claim 1 , wherein M 1 is a dimethylaminostilbene, quinacridone, fluorophenyl-dimethyl-BODIPY, bis-fluorophenyl-BODIPY, acridine, terrylene, sexiphenyl, porphyrin, benzopyrene, (fluorophenyl-dimethyl-difluorobora-diaza-indacene)phenyl, (bis-fluorophenyl-difluorobora-diaza-indacene)phenyl, quaterphenyl, bi-benzothiazole, ter-benzothiazole, bi-naphthyl, bi-anthracyl, squaraine, squarylium, 9, 10-ethynylanthracene or ter-naphthyl moiety.

9. The compound of claim 1 , wherein M 1 is p-terphenyl, perylene, azobenzene, phenazine, phenanthroline, acridine, thioxanthrene, chrysene, rubrene, coronene, cyanine, perylene imide, or perylene amide or derivative thereof.

10. The compound of claim 1 , wherein M 1 is a coumarin dye, resorufin dye, dipyrrometheneboron difluoride dye, ruthenium bipyridyl dye, energy transfer dye, thiazole orange dye, polymethine or N-aryl-1,8-naphthalimide dye.

11. The compound of claim 1 , wherein M 1 is pyrene, perylene, perylene monoimide or 6-FAM or derivative thereof.

12. The compound of claim 1 , wherein M 1 has one of the following structures:

13. A compound having the following structure (IIi):

wherein:
M 1 is a moiety comprising three or more aryl or heteroaryl rings, or combinations thereof;
R 1 is an unsubstituted C 1 -C 6 alkyl or an unsubstituted alkoxy;
R 2 is cyanoalkyl;
R 6 is an unsubstituted C 1 -C 6 alkyl; and
L 1 and L 4 are each independently unsubstituted alkylene or unsubstituted heteroalkylene linkers.

14. The compound of claim 13 , wherein each R 6 is isopropyl.

15. The compound of claim 13 , wherein R 2 is 2-cyanoethyl.

16. The compound of claim 13 , wherein L 1 and L 4 are each independently alkylene linkers.

17. The compound of claim 13 , wherein M 1 is fluorescent or colored.

18. The compound of claim 13 , wherein:
A) M 1 is a dimethylaminostilbene, quinacridone, fluorophenyl-dimethyl-BODIPY, his-fluorophenyl-BODIPY, acridine, terrylene, sexiphenyl, porphyrin, benzopyrene, (fluorophenyl-dimethyl-difluorobora-diaza-indacene)phenyl, (bis-fluorophenyl-difluorobora-diaza-indacene)phenyl, quaterphenyl, bi-benzothiazole, ter-benzothiazole, bi-naphthyl, bi-anthracyl, squaraine, squarylium, 9, 10-ethynylanthracene or ter-naphthyl moiety;
B) M 1 is p-terphenyl, perylene, azobenzene, phenazine, phenanthroline, acridine, thioxanthrene, chrysene, rubrene, coronene, cyanine, perylene imide, or perylene amide or derivative thereof;
C) M 1 is a coumarin dye, resorufin dye, dipyrrometheneboron difluoride dye, ruthenium bipyridyl dye, energy transfer dye, thiazole orange dye, polymethine or N-aryl-1,8-naphthalimide dye;
D) M 1 is pyrene, perylene, perylene monoimide or 6-FAM or derivative thereof, or
E) M 1 has one of the following structures:

Assignees

• Sony Group Corp

Inventors

• Matray Tracy
• Sherif Hesham
• Battrell C Frederick

Classifications

• C09B3/14 Primary

  Perylene derivatives · CPC title

• C07F9/094

  with arylalkanols · CPC title

• C07F9/098

  Esters of polyphosphoric acids or anhydrides · CPC title

• C07F9/5765

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07F9/65522

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title