Water soluble fluorescent or colored dyes and methods for their use
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.
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: