Fluorous dendrimers and methods for production thereof
The present invention concerns the design of an environmentally friendly and efficient fluorous phase based on dendritic architectures containing short semifluorinated groups on their periphery.
1. A method of producing a fluorous dendron comprising reacting a compound of formula II
with a compound of formula III
to produce a compound of the formula I
wherein:
R 1 is a C 1 -C 6 alkyl group;
each of R 2 -R 4 is, independently, H or OH; provided at least two of R 2 -R 4 are OH;
R 5 is a C 1 -C 9 perfluoroalkyl group, said C 1 -C 9 perfluoroalkyl group optionally containing 1 or 2 ether oxygens; and
each of R 6 -R 8 is, independently, H or a group of the formula
provided that at least two of R 6 -R 8 are a group of the formula
2. The method of claim 1 , wherein R 1 is methyl.
3. The method of claim 1 , wherein R 5 is a perfluoropropyl group.
4. The method of claim 1 , wherein said perfluoropropyl group is perfluoro-n-propyl.
5. The method of claim 1 , further comprising reacting the compound of formula I with a reducing agent to produce a compound of formula IV
6. The method of claim 5 , wherein said reducing agent is LiAlH 4 .
7. The method of claim 5 , further comprising reacting the compound of formula IV with a chlorinating agent to produce a compound of formula V
8. The method of claim 7 , wherein said chlorinating agent is SOCl 2 .
9. The method of claim 7 , further comprising reacting a compound of formula V with a compound of formula VI
to produce a compound of formula VII
wherein:
R 12 is a C 1 -C 6 alkyl group;
each of R 9 , R 10 and R 11 is independently H or OH; provided that at least two of R 9 , R 10 and R 11 are OH;
each of R 13 , R 14 and R 15 is independently H or a group of the formula VIII
provided that at least two of R 13 , R 14 and R 15 are of formula VIII.
10. A compound of the formula
wherein:
R 12 is a C 1 -C 6 alkyl group;
each of R 13 , R 14 and R 15 is independently H or a group of the formula VIII
provided that at least two of R 13 , R 14 and R 15 are of formula VIII;
each of R 6 -R 8 is, independently, H or a group of the formula
provided that at least two of R 6 -R 8 are a group of the formula
R 5 is a C 1 -C 9 perfluoroalkyl group, said C 1 -C 9 perfluoroalkyl group optionally containing 1 or 2 ether oxygens.
11. The compound of claim 10 , wherein R 12 is methyl.
12. The compound of claim 10 , wherein R 5 is a perfluoropropyl group.
13. The compound of claim 12 , wherein said perfluoropropyl group is perfluoro-n-propyl.
14. A compound of the formula
wherein:
R 1 is a C 1 -C 6 alkyl group;
R 5 is a C 1 -C 9 perfluoroalkyl group, said C 1 -C 9 perfluoroalkyl group optionally containing 1 or 2 ether oxygens; and
each of R 6 -R 8 is, independently, H or a group of the formula
provided that at least two of R 6 -R 8 are a group of the formula
15. The compound of claim 14 , wherein R 1 is methyl.
16. The compound of claim 15 , wherein R 5 is a perfluoropropyl group.
17. The compound of claim 16 , wherein said perfluoropropyl group is perfluoro-n-propyl.