Light sensitive PDMS for complex pattern formation
View Patent ↗Disclosed herein is a surface functionalized poly(dimethylsiloxane) (PDMS) and methods for making the same. The surface functionalized PDMS disclosed herein is applicable in the general field of microfluidics, bioMEMS (bio-microelectromechanical systems), soft lithography, and other related biotechnology fields.
1. A compound of formula I:
wherein:
R 1 is hydrogen or methyl;
R 2 is selected from the group consisting of alkyl optionally substituted with 1-3 R 4 groups, aryl optionally substituted with 1-4 R 4 groups, cycloalkyl optionally substituted with 1-4 R 4 groups, heterocycloalkyl optionally substituted with 1-4 R 4 groups, and heteroaryl optionally substituted with 1-4 R 4 groups;
X is O or NR 3 , where R 3 is hydrogen or alkyl;
L 1 and L 2 are independently selected from the group consisting of a direct bond, methylene optionally substituted with 1-2 R 4 groups, (C 2 -C 12 )alkylene optionally substituted with 1-4 R 4 groups, (C 6 -C 12 )arylene optionally substituted with 1-4 R 4 groups, and (C 3 -C 12 )cycloalkylene optionally substituted with 1-4 R 4 groups; and
each R 4 is independently selected from the group consisting of halo, nitro, cyano, oxo, aminoacyl, aminoacyloxy, carboxyl, carboxyl ester, carbonate ester, aminosulfonyl, (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 1 -C 10 )alkoxy, (C 6 -C 12 )aryl, (C 5 -C 12 )heteroaryl, (C 6 -C 12 )aryloxy, (C 3 -C 12 )cycloalkyl and (C 3 -C 12 )heterocycloalkyl.
2. The compound of claim 1 , wherein R 1 is hydrogen.
3. The compound of claim 1 , wherein R 2 is aryl.
4. The compound of claim 1 , wherein R 2 is phenyl.
5. The compound of claim 1 , wherein X is O.
6. The compound of claim 1 , wherein L 1 is (C 2 -C 12 )alkylene.
7. The compound of claim 1 , wherein L 1 is —(CH 2 ) 9 —.
8. The compound of claim 1 , wherein L 2 is (C 6 -C 12 )arylene.
9. The compound of claim 1 , wherein L 2 is phenylene.
10. The compound of claim 1 , wherein R 1 is hydrogen; R 2 is aryl; X is O; L 1 is (C 2 -C 12 )alkylene; and L 2 is (C 6 -C 12 )arylene.
11. A surface functionalized poly(dimethylsiloxane) (PDMS), comprising:
a poly(dimethylsiloxane) (PDMS) substrate having a linker of formula III incorporated therein:
wherein:
R 1 is hydrogen or methyl;
R 2 is selected from the group consisting of alkyl optionally substituted with 1-3 R 4 groups, aryl optionally substituted with 1-4 R 4 groups, cycloalkyl optionally substituted with 1-4 R 4 groups, heterocycloalkyl optionally substituted with 1-4 R 4 groups, and heteroaryl optionally substituted with 1-4 R 4 groups;
X is O or NR 3 , where R 3 is hydrogen or alkyl;
L 1 and L 2 are independently selected from the group consisting of a direct bond, methylene optionally substituted with 1-2 R 4 groups, (C 2 -C 12 )alkylene optionally substituted with 1-4 R 4 groups, (C 6 -C 12 )arylene optionally substituted with 1-4 R 4 groups, and (C 3 -C 12 )cycloalkylene optionally substituted with 1-4 R 4 groups; and
each R 4 is independently selected from the group consisting of halo, nitro, cyano, oxo, aminoacyl, aminoacyloxy, carboxyl, carboxyl ester, carbonate ester, aminosulfonyl, (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 1 -C 10 )alkoxy, (C 6 -C 12 )aryl, (C 5 -C 12 )heteroaryl, (C 6 -C 12 )aryloxy, (C 3 -C 12 )cycloalkyl and (C 3 -C 12 )heterocycloalkyl;
wherein said linker is bonded to an initiator compound through the pyrazole and the PDMS through the —(CH 2 )—.
12. The surface functionalized poly(dimethylsiloxane) (PDMS) of claim 11 , wherein R 1 is hydrogen.
13. The surface functionalized poly(dimethylsiloxane) (PDMS) of claim 11 , wherein X is O.
14. The surface functionalized poly(dimethylsiloxane) (PDMS) of claim 11 , wherein L 1 is (C 2 -C 12 )alkylene.
15. The surface functionalized poly(dimethylsiloxane) (PDMS) of claim 11 , wherein L 2 is (C 6 -C 12 )arylene.
16. The surface functionalized poly(dimethylsiloxane) (PDMS) of claim 11 , wherein R 1 is hydrogen; X is O; L 1 is (C 2 -C 12 )alkylene; and L 2 is (C 6 -C 12 )arylene.
17. The surface functionalized poly(dimethylsiloxane) (PDMS) of claim 11 , wherein the linker is incorporated therein at a ratio of from about 11:0.5 to about 11:10 −3 .
18. The surface functionalized poly(dimethylsiloxane) (PDMS) of claim 11 , wherein the contact angle is from about 110 to about 120 degrees.
19. The surface functionalized poly(dimethylsiloxane) (PDMS) of claim 11 , further comprising at least one indentation disposed on the surface of said PDMS substrate.
20. A method of preparing a surface functionalized poly(dimethylsiloxane) (PDMS), comprising:
1) providing a poly(dimethylsiloxane) (PDMS) substrate having a compound of formula I incorporated therein:
wherein:
R 1 is hydrogen or methyl;
R 2 is selected from the group consisting of alkyl optionally substituted with 1-3 R 4 groups, aryl optionally substituted with 1-4 R 4 groups, cycloalkyl optionally substituted with 1-4 R 4 groups, heterocycloalkyl optionally substituted with 1-4 R 4 groups, and heteroaryl optionally substituted with 1-4 R 4 groups;
X is O or NR 3 , where R 3 is hydrogen or alkyl;
L 1 and L 2 are independently selected from the group consisting of a direct bond, methylene optionally substituted with 1-2 R 4 groups, (C 2 -C 12 )alkylene optionally substituted with 1-4 R 4 groups, (C 6 -C 12 )arylene optionally substituted with 1-4 R 4 groups, and (C 3 -C 12 )cycloalkylene optionally substituted with 1-4 R 4 groups; and
each R 4 is independently selected from the group consisting of halo, nitro, cyano, oxo, aminoacyl, aminoacyloxy, carboxyl, carboxyl ester, carbonate ester, aminosulfonyl, (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 1 -C 10 )alkoxy, (C 6 -C 12 )aryl, (C 5 -C 12 )heteroaryl, (C 6 -C 12 )aryloxy, (C 3 -C 12 )cycloalkyl and (C 3 -C 12 )heterocycloalkyl; and
2) contacting said compound with an initiator compound under reaction conditions to provide a surface functionalized poly(dimethylsiloxane) (PDMS).