Highly fluorinated oils and surfactants and methods of making and using same
Disclosed are compounds comprising the structure: In one aspect, the compounds exhibit maximum symmetric branching. Also disclosed are bilayers, micelles, coatings, and nanoparticles comprising the disclosed compounds. Also disclosed are processes for the preparation of the disclosed compounds and methods of using the disclosed compounds. Also disclosed are highly fluorinated dendrons and methods for making same. Also disclosed are methods for Fluorous Mixture Synthesis and tagging. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
1. A compound comprising the structure:
wherein R 11 , R 12 , R 13 , R 21 , R 22 , R 23 , R 31 , R 32 , and R 33 are CF 3 ; and
wherein R 4 is H, OH, OBn, OC(CF 3 ) 3 , alkyl, or alkoxy.
2. The compound of claim 1 , wherein the compound is a surfactant.
3. The compound of claim 1 , comprising a structure selected from:
wherein n is from 2 to 10.
4. The compound of claim 1 , wherein the compound is an oil.
5. The compound of claim 1 , comprising a structure selected from:
6. The compound of claim 1 , wherein the compound exhibits maximum symmetric branching.
7. A process for the preparation of a compound comprising the structure:
wherein R is CF 3 and wherein R 4 is H, OH, OBn, alkyl, or alkoxy;
the process comprising the steps of:
providing a triol,
reacting the triol with or nonafluoro-tert-butanol to provide a triperfluoro-tert-butyl ether.
8. The process of claim 7 , wherein the compound comprises the structure:
wherein n is 0 or a positive integer;
wherein R 51 , R 52 , R 61 , and R 62 are, independently, H or alkyl; and
wherein R 7 , R 8 , and R 9 are, independently, H, CH 2 CO 2 H, or alkyl.
9. The process of claim 8 , wherein n is an integer from 4 to 12.
10. A delivery method comprising the steps of:
a. complexing a payload with one or more compounds of claim 6 ; and
b. administering the complex to a mammal in an effective amount.
11. The method of claim 10 , comprising the steps of:
a. complexing a metal ion with a compound of claim 6 ; and
b. administering the complex to a subject in an amount effective for detection by 1 H MRI.
12. The method of claim 10 , comprising the steps of:
a. complexing a radionuclide with a compound of claim 6 ; and
b. administering the complex to a mammal in an amount effective for radiotherapy.