Fluorescent halogen bonding arylethynyl scaffolds for anion recognition

Patent metadata

Field	Value
Publication number	US-11021447-B2
Application number	US-201916401037-A
Country	US
Kind code	B2
Filing date	May 1, 2019
Priority date	May 14, 2018
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

A compound, or a protonate or salt thereof, of formula I:

wherein Y is aryl, substituted aryl, heteroaryl, or substituted heteroaryl;
n is 1 or 2;
each R 10 is independently alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, aryl, substituted aryl, cyano, hydroxyl, carbonylamino, aminocarbonyl, acyl, sulfonyl, or substituted sulfonyl;
a is 0 to 4;

is an aryl or heteroaryl ring; and
each R is independently halogen, carbonylamino, sulfonamide, carboxylic acid or hydrogen, provided at least one R is a halogen; and provided that if Y is

are not

respectively.

First claim

What is claimed is:

1. A compound, or a protonate or salt thereof, of formula I:

wherein Y is

wherein Z is hydrogen, halogen, amino, substituted amino, hydroxy, amido, urea or sulfonamido; and R 7 is hydrogen, alkyl, substituted alkyl, or polyethylene glycol;
n is 1 or 2;
each R 10 is independently ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, decyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, aryl, substituted aryl, cyano, hydroxyl, carbonylamino, aminocarbonyl, acyl, sulfonyl, or substituted sulfonyl;
a is 1 to 4;

is an aryl or heteroaryl ring; and
each R is independently halogen, carbonylamino, sulfonamide, carboxylic acid or hydrogen, provided at least one R is a halogen.

2. The compound of claim 1 , wherein
R 7 is C 1 -C 6 alkyl, alkoxyalkyl, aminoalkyl or sulfonylalkyl.

3. The compound of claim 2 , wherein R 7 is methyl.

4. The compound of claim 1 , wherein Z is —NH 2 , —Br, or —I.

5. The compound of claim 1 , wherein n is 1.

6. The compound of claim 1 , wherein a is 1.

7. The compound of claim 1 , wherein the

portions of the compound of formula I are:

respectively, or

respectively, or

respectively.

8. The compound of claim 1 , wherein R 10 is substituted alkyl, substituted sulfonyl, or substituted carboxyl.

9. The compound of claim 1 , wherein R 10 is —CF 3 , sulfonylC 1-6 alkyl, or —COOR wherein R is alkyl.

10. The compound of claim 1 , wherein a is 1 and both R 10 are the same.

11. The compound of claim 1 , wherein at least one R is —I.

12. The compound of claim 1 , wherein both R groups are —I.

13. The compound of claim 1 , wherein the compound is protonated.

14. The compound of claim 1 , wherein the

portions of the compound of formula I are:

respectively.

15. The compound of claim 14 , wherein both R groups are —I.

16. A receptor-ligand structure comprising the compound of claim 1 as a receptor and a ligand.

17. A receptor-ligand structure comprising the compound of claim 1 as a receptor and a ligand that includes at least one anion selected from Cl − , Br − , I − , H 2 PO 4 − , HSO 4 − , ClO 4 − , NO 3 − , PF 6 − , TsO − , OTf − , BAr F− , BF 4 − , HS − , SbF 6 − , ReO 4 − , TcO 4 − or SCN − .

18. A method for detecting for the presence of an anion in a system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, of claim 1 .

19. A compound, or a protonate or salt thereof, of formula I:

wherein Y is

wherein R 7 is C 1 -C 6 alkyl, alkoxyalkyl, aminoalkyl or sulfonylalkyl, and Z is halogen, amino, substituted amino, hydroxy, amido, urea or sulfonamido;
n is 1 or 2;
each R 10 is independently alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, aryl, substituted aryl, cyano, hydroxyl, carbonylamino, aminocarbonyl, acyl, sulfonyl, or substituted sulfonyl;
a is 0 to 4;

is an aryl or heteroaryl ring; and
each R is independently halogen, carbonylamino, sulfonamide, carboxylic acid or hydrogen, provided at least one R is a halogen.

20. The compound of claim 19 , wherein a is 0.

21. The compound of claim 19 , wherein at least one R is —I.

22. The compound of claim 19 , wherein both R groups are —I.

23. The compound of claim 19 , wherein Z is —NH 2 , —Br, or —I.

24. The compound of claim 19 , wherein Z is amino.

25. A compound, or a protonate or salt thereof, of formula I:

wherein Y is

wherein Z is hydrogen, halogen, amino, substituted amino, hydroxy, amido, urea or sulfonamido; and R 7 is hydrogen, alkyl, substituted alkyl, or polyethylene glycol;
n is 1 or 2;
each R 10 is independently alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, aryl, substituted aryl, cyano, hydroxyl, carbonylamino, aminocarbonyl, acyl, sulfonyl, or substituted sulfonyl;
a is 0 to 4;

is an aryl or heteroaryl ring; and
each R is independently halogen, carbonylamino, sulfonamide, carboxylic acid or hydrogen, provided at least one R is —I; and
provided that if Y is

then

are not

respectively.

26. The compound of claim 25 , wherein the

portions of the compound of formula I are:

respectively.

27. The compound of claim 25 , wherein both R groups are —I.

Assignees

• Univ Oregon
• Univ Of Montana

Inventors

• Lohrman Jessica
• Johnson Darren W
• Haley Michael M
• Berryman Orion B
• Riel Asia M
• Decato Daniel A

Classifications

• C07D233/56 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms · CPC title

• C07D213/90

  having more than three double bonds between ring members or between ring members and non-ring members · CPC title

• C07D213/22 Primary

  containing two or more pyridine rings directly linked together, e.g. bipyridyl · CPC title

• G01N21/6428

  Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" (in vivo A61B5/00; immunoassay G01N33/53) · CPC title