Functionalized F-POSS monomer compositions and uses thereof

1. A compound having the formula:

wherein,

R 1 is a long chain fluorinated alkyl having from 5 to 12 carbon atoms;

R 2 is propyl substituted by an R 3 ;

R 3 is —OC(O)OR 4 ;

R 4 is selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 3-7 membered heterocyclic, and 5-7 membered heteroaryl, wherein each hydrogen atom in R 4 and R 5 is independently optionally substituted by an R 6 ;

each R 6 is independently selected from the group consisting of halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 3-7 membered heterocyclic, 5-7 membered heteroaryl, —NCO, —OR 7 , —NR 7 R 8 , —C(O)OR 7 ,—C(O)R 7 , —OC(O)OR 7 , —C(O)NR 7 R 8 , —OC(O)NR 7 R 8 , —NR 7 C(O)R 8 , —NR 7 C(O)OR 8 and —NR 7 C(O)NR 7 R 8 , and when R 6 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic or 5-7 membered heteroaryl, each hydrogen atom in R 6 is independently optionally substituted by an R 9 ;

each R 7 and R 8 is independently selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic and 5-7 membered heteroaryl, wherein each hydrogen atom in R 7 and R 8 is independently optionally substituted by one or more R 9 ;

each R 9 is independently selected from the group consisting of hydrogen, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic, 5-7 membered heteroaryl, —NCO, —OR 10 , —NR 10 R 11 , —OC(O)R 10 , —C(O)OR 10 , —C(O)R 10 , —OC(O)OR 10 , —C(O)NR 10 R 11 , —OC(O)NR 10 R 11 , —NR 10 C(O)R 11 , —NR 10 C(O)OR 11 and —NR 10 C(O)NR 10 R 11 , and when R 9 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic, C 3 -C 8 cycloalkyl or 5-7 membered heteroaryl, each hydrogen in R 9 is independently optionally substituted by a moiety selected from the group consisting of halo, —NCO, —OR 10 , —NR 10 R 11 , —C(O)OR 10 , —C(O)R 10 , —OC(O)OR 10 , —C(O)NR 10 R 11 , —OC(O)NR 10 R 11 , —NR 10 C(O)R 11 , —NR 10 C(O)OR 11 and —NR 10 C(O)NR 10 R 11 ;

each R 10 and R 11 is independently selected from the group consisting of H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl and C 2 -C 8 alkynyl, and when R 10 or R 11 are either C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkynyl, each hydrogen atom in R 10 and R 11 is independently optionally substituted by a fluorine atom;

n is an integer from 1 to 7; and,

each R 1 and R 2 is independently covalently attached at a silicon atom.

2. The compound of claim 1 , wherein R 4 is C 1 -C 8 alkyl and wherein each hydrogen atom in R 4 is independently optionally substituted by an R 6 .

3. The compound of claim 2 , wherein R 6 is either C 1 -C 8 alkyl, —NCO, —OR 7 , —NR 7 R 8 , —OC(O)R 7 , —C(O)OR 7 , —C(O)R 7 or —OC(O)OR 7 .

4. The compound of claim 3 , wherein R 7 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl or 5-7 membered heteroaryl, wherein each hydrogen atom in R 7 is independently optionally substituted by one or more R 9 .

5. The compound of claim 2 , wherein R 6 is either C 1 -C 8 alkyl, —NCO, -OR 7 , —NR 7 R 8 ,—OC(O)R 7 , —C(O)OR 7 , —C(O)R 7 or —OC(O)OR 7 .

6. The compound of claim 1 , R 4 is C 2 -C 8 alkenyl, wherein each hydrogen atom in R 4 is independently optionally substituted by an R 6 .

7. The compound of claim 6 , wherein R 6 is either C 1 -C 8 alkyl, —NCO, —OR 7 , —NR 7 R 8 , —OC(O)R 7 , —C(O)OR 7 , —C(O)R 7 or —OC(O)OR 7 .

8. The compound of claim 7 , wherein R 7 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl or 5-7 membered heteroaryl, wherein each hydrogen atom in R 7 is independently optionally substituted by one or more R 9 .

9. The compound of claim 1 , wherein R 6 is either C 1 -C 8 alkyl, —NCO, —OR 7 , —NR 7 R 8 , —OC(O)R 7 , —C(O)OR 7 , —C(O)R 7 or —OC(O)OR 7 .

10. The compound of claim 1 , wherein R 7 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl or 5-7 membered heteroaryl, wherein each hydrogen atom in R 7 is independently optionally substituted by one or more R 9 .

11. The compound of claim 1 , wherein R 9 is either hydrogen or C 1 -C 8 alkyl, and when R 9 is C 1 -C 8 alkyl, R 9 is optionally substituted by a —OC(O)R 10 .

12. The compound of claim 1 , wherein R 10 is either H or C 1 -C 8 alkyl, and when R 10 is C 1 -C 8 alkyl, each hydrogen atom in R 10 is independently optionally substituted by a fluorine atom.

13. The compound claim 1 , wherein the long chain fluorinated alkyl is either 8/2, 6/2 or 4/2.

14. A compound having the formula:

wherein,

R 1 is a long chain fluorinated alkyl having from 5 to 12 carbon atoms;

R 2 is propyl, wherein each hydrogen atom is independently optionally substituted by an R 3 ;

each R 3 is selected from the group consisting of halo, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 3-7 membered heterocyclic, 5-7 membered heteroaryl, —NCO, —OR 4 , —NR 4 R 5 , —C(O)OR 4 , —C(O)R 4 , —OC(O)OR 4 , —C(O)NR 4 R 5 , —OC(O)NR 4 R 5 , —NR 4 C(O)R 5 , —NR 4 C(O)OR 5 and —NR 4 C(O)NR 4 R 5 , and when R 3 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic or 5-7 membered heteroaryl, each hydrogen atom in R 3 is independently optionally substituted by an R 6 ;

R 4 is —CH═CH 2 , wherein each hydrogen atom in R 4 is independently optionally substituted by methyl;

each R 6 is independently selected from the group consisting of halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 3-7 membered heterocyclic, 5-7 membered heteroaryl, —NCO, —OR 7 , —NR 7 R 8 , —C(O)OR 7 , —C(O)R 7 , —OC(O)OR 7 , —C(O)NR 7 R 8 , —OC(O)NR 7 R 8 , —NR 7 C(O)R 8 , —NR 7 C(O)OR 8 and —NR 7 C(O)NR 7 R 8 , and when R 6 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic or 5-7 membered heteroaryl, each hydrogen atom in R 6 is independently optionally substituted by an R 9 ;

each R 7 and R 8 is independently selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic and 5-7 membered heteroaryl, wherein each hydrogen atom in R 7 and R 8 is independently optionally substituted by one or more R 9 ;

each R 9 is independently selected from the group consisting of hydrogen, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic, 5-7 membered heteroaryl, —NCO, —OR 10 , —NR 10 R 11 , —OC(O)R 10 , —C(O)OR 10 , —C(O)R 10 , —OC(O)OR 10 , —C(O)NR 10 R 11 , —OC(O)NR 10 R 11 , —NR 10 C(O)R 11 , —NR 10 C(O)OR 11 and —NR 10 C(O)NR 10 R 11 , and when R 9 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl, C 3 -C 8 cycloalkyl, 5-7 membered heterocyclic, C 3 -C 8 cycloalkyl or 5-7 membered heteroaryl, each hydrogen in R 9 is independently optionally substituted by a moiety selected from the group consisting of halo, —NCO, —OR 10 , —NR 10 R 11 , —C(O)OR 10 , —C(O)R 10 , —OC(O)OR 10 , —C(O)NR 10 R 11 , —OC(O)NR 10 R 11 , —NR 10 C(O)R 11 , —NR 10 C(O)OR 11 and —NR 10 C(O)NR 10 R 11 ;

each R 10 and R 11 is independently selected from the group consisting of H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl and C 2 -C 8 alkynyl, and when R 10 or R 11 are either C 1 -C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkynyl, each hydrogen atom in R 10 and R 11 is independently optionally substituted by a fluorine atom;

n is an integer from 1 to 6; and,

each R 1 and R 2 is independently covalently attached at a silicon atom.

15. The compound of claim 14 , wherein R 3 is either —NCO, —OR 4 , —OC(O)R 4 , —C(O)OR 4 , —C(O)R 4 or —OC(O)OR 4 .

16. The compound of claim 14 , wherein R 6 is either C 1 -C 8 alkyl, —NCO, —OR 7 , —NR 7 R 8 , —OC(O)R 7 , —C(O)OR 7 , —C(O)R 7 or —OC(O)OR 7 .

17. The compound of claim 14 , wherein R 7 is either C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 6 -C 10 aryl or 5-7 membered heteroaryl, wherein each hydrogen atom in R 7 is independently optionally substituted by one or more R 9 .

18. The compound of claim 14 , wherein R 9 is either hydrogen or C 1 -C 8 alkyl, and when R 9 is C 1 -C 8 alkyl, R 9 is optionally substituted by a —OC(O)R 10 .

19. The compound of claim 14 , wherein R 10 is either H or C 1 -C 8 alkyl, and when R 10 is C 1 -C 8 alkyl, each hydrogen atom in R 10 is independently optionally substituted by a fluorine atom.

20. The compound claim 14 , wherein the long chain fluorinated alkyl is either 8/2, 6/2 or 4/2.