초록

This invention provides mixed-mode stationary phase compositions, devices and systems comprising the stationary phases as well as methods of producing these compositions using epoxide ring-opening reactions. Also provided are methods of using the stationary phases of the invention in separations.

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1. A composition comprising a compound covalently bound to a substrate, said compound having a structure according to Formula (I): in which n is an integer selected from 0 and 1;X is selected from the group consisting of NRfR21R22, SRf or ORf wherein, when X is NRfR21R22, Rf is selected from the gro

1. A composition comprising a compound covalently bound to a substrate, said compound having a structure according to Formula (I): in which n is an integer selected from 0 and 1;X is selected from the group consisting of NRfR21R22, SRf or ORf wherein, when X is NRfR21R22, Rf is selected from the group consisting of unsubstituted alkyl or substituted alkyl with at least one member selected from carboxylic acid, sulfonic acid, phosphoric acid, and an amino moiety and unsubstituted heteroalkyl or substituted heteroalkyl with at least one member selected from carboxylic acid, sulfonic acid, phosphoric acid, and an amino moiety;R21 is selected from the group consisting of H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl; andR22 is selected from the group consisting of a lone pair of electrons, H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl:wherein when X is SRf or ORf, Rf is substituted alkyl or substituted heteroalkyl each with at least one member selected from carboxylic acid, sulfonic acid, phosphoric acid and an amino acid;R1, R2 and R3 are selected independently from the group consisting of halogen, OR10, NR10R11, OC(O)R12, OS(O)2R12, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl and a bond to said substrate wherein each R10 and each R11 is selected independently from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl and a bond to a silica gel substrate,with the proviso that at least one of R1, R2 and R3 is unsubstituted C1-C3 alkyl or OH, and further with the proviso that at least one of R1, R2 and R3 is covalently bound to said substrate;each R12 is selected independently from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heterocycloalkyl;L1 and L2 are linker groups independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and substituted or unsubstituted heterocycloalkyl; andY is O. 2. The composition of claim 1, wherein R1, R2 and R3 are selected independently from the group consisting of OR10, OC(O)R12, OS(O)2R12, and unsubstituted alkyl, wherein each R10 and each R11 is selected independently from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl and a bond to a silica gel substrate;each R12 is selected independently from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heterocycloalkyl;L1 is C3 unsubstituted alkyl; andL2 is C1-C8 unsubstituted alkyl. 3. The composition of claim 1, wherein the structure is according to Formula (II): 4. The composition of claim 2, wherein R21 is unsubstituted alkyl and R22 is unsubstituted alkyl. 5. The composition of claim 2, wherein R21 is unsubstituted C1 or C2 or C3 alkyl and R22 is unsubstituted C1 or C2 or C3 alkyl. 6. The composition of claim 2, wherein R22 is a lone pair of electrons. 7. The composition of claim 2, wherein R21 is H and R22 is a lone pair of electrons. 8. The composition of claim 1, wherein Rf is alkyl substituted with a member selected from carboxylic acid, sulfonic acid, phosphoric acid, an amino acid and a combination thereof. 9. The composition of claim 1, wherein the structure is according to Formula (III): 10. The composition of claim 9, wherein Rf is alkyl substituted with a carboxylic acid. 11. The composition of claim 1, with the proviso that at least two of R1, R2 and R3 is covalently bound to said substrate. 12. The composition of claim 1, with the proviso that R1 and Rare covalently bound to said substrate and further, R3 is unsubstituted C1-C3 alkyl or OH. 13. The composition of claim 1, with the proviso that R1 and R2 are covalently bound to said substrate, and R3 is methyl. 14. The composition of claim 1, with the proviso that R1 and R2 are covalently bound to said substrate, and R3 is OH. 15. The composition of claim 1, wherein n is 0, and L2 is C1-C8 unsubstituted alkyl. 16. The composition of a claim 1, wherein n is 0, and L2 is C5-C8 unsubstituted alkyl. 17. The composition of claim 1, wherein n is 0, and L2 is C8 unsubstituted alkyl. 18. The composition of claim 1, wherein n is 1, and L1 is C2-C5 unsubstituted alkyl, and L2 is C1-C3 unsubstituted alkyl. 19. The composition of claim 1, wherein n is 1, and L1 is C3 unsubstituted alkyl, and L2 is C1 unsubstituted alkyl. 20. A chromatographic system comprising the composition of claim 1 in a chromatographic column in fluidic communication with one or more of: a) a suppressor;b) an injection valve;c) a source of eluent; andd) a detector. 21. The composition of claim 3, wherein, Rf is an unsubstituted alkyl. 22. The composition of claim 3, wherein, Rf is an unsubstituted heteroalkyl.