Colorimetric sensors constructed of diacetylene materials
Colorimetric sensors comprising a receptor incorporated within polydiacetylene assemblies to form a transducer capable of indicating a color change when contacted with an analyte are disclosed. Methods of using the colorimetric sensor and a kit for the colorimetric detection of an analyte are also disclosed.
1. A colorimetric sensor for detecting an analyte, comprising:
a receptor; and
a polymerized composition comprising at least one compound of the formula
R 3 , R 8 , R 13 , R 21 , R 24 , R 31 and R 33 are independently C 1 -C 20 alkyl;
R 4 , R 7 , R 14 , R 16 , R 19 , R 20 , R 22 , R 25 , and R 32 are independently C 1 -C 14 alkylene;
R 6 , R 15 , R 18 , and R 26 are independently C 1 -C 14 alkylene, C 2 -C 8 alkenylene, or C 6 -C 13 arylene;
R 9 is C 1 -C 14 alkylene or —NR 34 —;
R 10 , R 12 , R 27 , and R 29 are independently C 1 -C 14 alkylene or (C 1 -C 14 alkylene)-(C 2 -C 8 arylene);
R 11 and R 28 are independently C 2 -C 30 alkynyl;
R 17 is an ester-activating group;
R 23 is C 6 -C 13 arylene;
R 30 is C 1 -C 14 alkylene or —NR 36 —;
R 34 , and R 36 are C 1 -C 4 alkyl;
p is 1-5;
n is 1-20;
wherein R 1 and R 2 are not the same;
wherein the receptor is incorporated into the polymerized composition to form a transducer; and
wherein the transducer exhibits a color change when contacted with an analyte.
2. The sensor of claim 1 , wherein R 1 is dodecyl or hexadecyl.
3. The sensor of claim 1 , wherein R 3 is undecyl or pentadecyl.
4. The sensor of claim 1 , wherein R 24 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, or dodecyl.
5. The sensor of claim 1 , wherein R 33 is dodecyl, tetradecyl, hexadecyl, or octadecyl.
6. The sensor of claim 1 , wherein R 4 is methylene, trimethylene, or tetramethylene.
7. The sensor of claim 1 , wherein R 7 , R 16 , R 19 , R 20 and R 25 are independently ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, or nonamethylene.
8. The sensor of claim 1 , wherein R 20 is methylene, trimethylene, or tetramethylene.
9. The sensor of claim 1 , wherein R 22 is ethylene, trimethylene, or tetramethylene.
10. The sensor of claim 1 , wherein R 32 is ethylene, trimethylene, tetramethylene, pentamethylene, or hexamethylene.
11. The sensor of claim 1 , wherein R 6 , R 15 , R 18 , and R 26 are independently ethylene, trimethylene, ethenylene, or phenylene.
12. The sensor of claim 1 , wherein R 8 and R 31 are independently C 1 -C 14 alkyl.
13. The sensor of claim 12 , wherein R 8 and R 31 are independently butyl, pentyl or hexyl.
14. The sensor of claim 1 , wherein R 9 and R 30 are independently methylene, NH-, -N(CH 2 CH 3 )-, or -N(CH 3 ) -.
15. The sensor of claim 1 , wherein R 10 , R 12 , R 27 , and R 29 are independently methylene, ethylene, trimethylene, tetramethylene, -C(CH 3 ) 2 -, CH((CH 2 ) 1-4 CH 3 )-, or - CH 2 -phenylene.
16. The sensor of claim 1 , wherein R 11 and R 28 are independently C 2 -C 30 alkynyl having at least two carbon-carbon triple bonds.
17. The sensor of claim 16 , wherein R 11 and R 28 are independently - (CH 2 ) 8 -C≡C-C≡C-(CH 2 ) 9 CH 3 , or -(CH 2 ) 8 -C≡C-C≡C-(CH 2 ) 11 CH 3 .
18. The sensor of claim 1 , wherein R 13 is C 1 -C 4 alkyl.
19. The sensor of claim 1 , wherein R 14 is C 1 -C 4 alkylene.
20. The sensor of claim 1 , wherein R 17 is 2,5-dioxo-1-pyrrolidinyl.
21. The sensor of claim 1 , wherein R 23 is phenylene.
22. The sensor of claim 1 , wherein n 3-17, 6-14, or 9-11.
23. The sensor of claim 1 , wherein p is 1 or 2.
24. The sensor of claim 1 wherein R 1 is
wherein R 7 is ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, or nonamethylene, and R 6 is ethylene, trimethylene, ethenylene, or phenylene; and
wherein R 2 is
wherein R 20 is ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, or nonamethylene, and wherein R 21 is undecyl, tridecyl, pentadecyl, heptadecyl; and
wherein p is 1.
25. The sensor of claim 24 , wherein R 1 is
R 20 is tetramethylene, and wherein R 21 is tridecyl; and
p is 1.
26. The sensor of claim 1 , wherein the receptor is selected from the group consisting of phospholipid and glycerol.
27. The sensor of claim 1 , wherein the transducer is dispersed in an aqueous solution.
28. The sensor of claim 1 , wherein the transducer is coated on a substrate.
29. The sensor of claim 28 , wherein the substrate exhibits a contact angle less than 50 degrees using methylene iodide.
30. The sensor of claim 29 , wherein the substrate is selected from the group consisting of silica gel plate, paper, glass, textured photo paper, gloss photo paper, and microporous film.
31. The sensor of claim 1 , wherein the receptor is incorporated into the polymerized composition by physical mixing.
32. The sensor of claim 1 , wherein the receptor is incorporated into the polymerized composition by covalently binding the receptor to the polymerized composition.