Sulfonate modified nanocrystals
AssigneeLife Technologies Corporation
InventorsEric Tulsky, Eric Welch, Bruce Branchaud, John Mauro, Imad Naasani
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Abstract
A nanoparticle having one or more phosphonates or phosphinate ligands on their surface can be converted into nanoparticles with sulfonate ligands on their surface, by contacting the phosphonate-containing nanoparticles with a silylsulfonate reagent. Such nanoparticles are activated toward reactions with nucleophilic groups; thus the method provides activated nanoparticles, and methods of making and using them to produce modified nanoparticles.
Claims42
A population of nanoparticles, comprising:
- a plurality of nanoparticles,
- wherein each nanoparticle includes a nanocrystal core including a first semiconductor material, a shell including a second semiconductor material, and an outer layer comprised of sulfonate, nitrate, borate, or fluorous anion ligands.
A method for preparing a nanoparticle coated with sulfonate ligands, comprising:
- providing the nanoparticle coated with a surface layer comprising a phosphonate, phosphinate, or carboxylate ligand;
- and
- contacting the nanoparticle with a silylsulfonate, silylnitrate, silylborate, or silyl fluorous anion reagent in an organic solvent.
A method for preparing water-dispersible nanoparticles, comprising:
- providing a sulfonate, nitrate, borate, or fluorous anion ligand coated nanocrystal dispersed in an organic solvent;
- contacting the sulfonate, nitrate, borate, or fluorous anion ligand coated nanocrystal with a functionalized organic molecule comprising at least one nanocrystal surface attachment group;
- contacting the nanocrystal dispersion with an aqueous solution to form a biphasic mixture having an aqueous phase and a non-aqueous phase;
- and
- maintaining the biphasic mixture under conditions that cause the nanocrystal to migrate from the non-aqueous phase into the aqueous phase.
A method to prepare a nanocrystal with a surface attached functionalized organic molecule, comprising:
- providing a nanocrystal having a surface attached sulfonate, nitrate, borate, or fluorous anion group;
- and
- contacting the nanocrystal with a functionalized organic molecule comprising at least one available nucleophilic reactant group in an organic solvent.
A method to replace a phosphonate ligand, phosphinate, or carboxylate ligand on a nanocrystal surface, comprising
- contacting the nanocrystal with a silylsulfonate, silylnitrate, silylborate, or silyl fluorous anion reagent to make an activated nanocrystal comprising sulfonate, nitrate, borate, or fluorous anion groups on its surface;
- and
- contacting the activated nanocrystal with a functionalized organic molecule comprising at least one available nucleophilic reactant group in an organic solvent.
A method of preparing a nanoparticle of Formula (II), comprising:
- providing a nanocrystal coated with sulfonate groups;
- and
- reacting the nanocrystal with a dithiol compound of the Formula (III)
- whereby at least two sulfonate groups on the surface of the nanocrystal are replaced by the dithiol compound, thereby providing the nanoparticle of Formula (II), wherein the shaded sphere represents a nanocrystal;
- n is an integer from 0 to 1;
- m is an integer from 0 to 10;
- p is an integer from 1 to 4;
- q is an integer from 4 to 50;
- and
- Z is a functional group selected from COOR1, CONR1R2, SO3R1, PO3R1, OR1, NR1R2, SO2NR1R2, NR1SO2R1, NR1C(═O)R1, CN, biotin, avidin, and streptavidin;
- wherein each R1 and R2 is independently H or an optionally substituted C1-C4 alkyl, where the alkyl is optionally substituted with one or more groups selected from halo, C1-C4 alkoxy, CN, OH, and COOH;
- or Z is a linker connecting the PEG moiety to a biomolecule.
A method of preparing a nanoparticle of Formula (V), comprising:
- providing a nanocrystal coated with sulfonate groups;
- reacting the nanocrystal with a dithiol compound of the Formula (IV)
- whereby at least two sulfonate groups on the surface of a nanocrystal are replaced by the dithiol compound, to provide the nanoparticle of Formula (V),
- and
- reacting the nanoparticle of Formula (V) with an amine compound of Formula (VI),
- thereby providing the nanoparticle of Formula (II);
- wherein the shaded sphere represents a nanocrystal;
- n is an integer from 0 to 1;
- m is an integer from 0 to 10;
- p is an integer from 1 to 4;
- q is an integer from 4 to 50;
- and
- Z is a functional group selected from COOR1, CONR1R2, SO3R1, PO3R1, OR1, NR1R2, SO2NR1R2, NR1SO2R1, NR1C(═O)R1, CN, biotin, avidin, and streptavidin;
- wherein each R1 and R2 is independently H or an optionally substituted C1-C4 alkyl, where the alkyl is optionally substituted with one or more groups selected from halo, C1-C4 alkoxy, CN, OH, and COOH;
- or Z is a linker connecting the PEG moiety to a biomolecule;
Dependencies are inferred from the claim text.