Chemical functionalization of surfaces
First Claim
1. A method for producing a functionalized surface on a substance, comprising the steps:
- (a) providing a non-fluid substrate having a surface comprising surface molecules having chemical moieties each capable of undergoing an addition reaction with a nitrene;
(b) providing a first functionalizing reagent comprising molecules each having a nitrenogenic group and a first functional group, the first functionalizing reagent being selected from the group consisting of functionalized perfluorophenyl azides having the structure;
##STR22## wherein X is selected from the group consisting of CN;
CONH2 ;
CHO;
CO2 CH3 ;
COCH3 ;
NO2 ;
CO2 H;
COCl;
CO-imidazole;
CONHS;
CH2 OH;
CH2 NH2 ;
COCH2 Br;
N-maleimido;
NH-biotinyl;
CONH--R, wherein R is a polypeptide;
CONH--X--S--S--Y--NH-biotinyl, wherein X and Y are spacer atoms; and
CONHS--SO3 Na;
(c) applying the first functionalizing reagent to the substrate surface; and
(d) either subsequent to or simultaneously with step (c), exposing preselected regions on the substrate surface to a reaction-energy source so as to convert the nitrenogenic groups, on molecules of the first functionalizing reagent on the surface, to nitrenes that undergo addition reactions with the chemical moieties on the surface molecules, thereby covalently bonding the first functional groups to the surface molecules to create a pattern of functionalized surface regions relative to non-functionalized regions.
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Abstract
Methods for covalently modifying surfaces of various substrates are disclosed, along with various substrates having surfaces modified by such methods. Candidate surfaces include various polymeric, siliceous, metallic, allotrophic forms of carbon, and semiconductor surfaces. The surfaces are exposed to a reagent, having molecules each comprising a nitrenogenic group and a functionalizing group, in the presence of energized charged particles such as electrons and ions, photons, or heat, which transform the nitrenogenic reagent to a nitrene intermediate. The nitrene covalently reacts with any of various chemical groups present on the substrate surface, thereby effecting nitrene addition of the functionalizing groups to the substrate surface. The functionalizing groups can then participate in downstream chemistry whereby any of a large variety of functional groups, including biological molecules, can be covalently bonded to the surface, thereby dramatically altering the chemical behavior of the surface. Such functionalizations of the surface can be done in a single reactive step or in multiple reactive steps.
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Citations
29 Claims
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1. A method for producing a functionalized surface on a substance, comprising the steps:
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(a) providing a non-fluid substrate having a surface comprising surface molecules having chemical moieties each capable of undergoing an addition reaction with a nitrene; (b) providing a first functionalizing reagent comprising molecules each having a nitrenogenic group and a first functional group, the first functionalizing reagent being selected from the group consisting of functionalized perfluorophenyl azides having the structure;
##STR22## wherein X is selected from the group consisting of CN;
CONH2 ;
CHO;
CO2 CH3 ;
COCH3 ;
NO2 ;
CO2 H;
COCl;
CO-imidazole;
CONHS;
CH2 OH;
CH2 NH2 ;
COCH2 Br;
N-maleimido;
NH-biotinyl;
CONH--R, wherein R is a polypeptide;
CONH--X--S--S--Y--NH-biotinyl, wherein X and Y are spacer atoms; and
CONHS--SO3 Na;(c) applying the first functionalizing reagent to the substrate surface; and (d) either subsequent to or simultaneously with step (c), exposing preselected regions on the substrate surface to a reaction-energy source so as to convert the nitrenogenic groups, on molecules of the first functionalizing reagent on the surface, to nitrenes that undergo addition reactions with the chemical moieties on the surface molecules, thereby covalently bonding the first functional groups to the surface molecules to create a pattern of functionalized surface regions relative to non-functionalized regions. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 23)
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20. A method for producing a functionalized surface on a substance, comprising the steps:
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(a) providing a non-fluid substrate having a surface comprising surface molecules having chemical moieties each capable of undergoing an addition reaction with a nitrene; (b) providing a first functionalizing reagent comprising molecules each having a nitrenogenic group and a first functional group; (c) providing a second functionalizing reagent comprising molecules each having a second functional group reactive with the first functional group; (d) adding the first functionalizing reagent to the second functionalizing reagent under conditions conducive for an addition reaction of the first functional group with the second functional group so as to cause molecules of the second functionalizing reagent to bond to molecules of the first functionalizing reagent, thereby forming a reaction product of molecules each comprising a molecule of the first functionalizing reagent bonded to a molecule of the second functionalizing reagent; (e) applying molecules of the reaction product to the substrate surface; (f) either subsequent to or simultaneously with step (e), exposing the surface to a reaction-energy source so as to convert the nitrenogenic groups, on molecules of the reaction product on the surface, to nitrenes that undergo addition reactions with the chemical moieties on the surface molecules, thereby covalently bonding molecules of the reaction product to the surface molecules. - View Dependent Claims (24)
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21. A method for functionalizing a polymeric substrate, comprising the steps:
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(a) providing a polymeric material comprised of polymer molecules possessing at least one reactive group selected from a group consisting of --NH, --CH, --OH, --C--C--, and --C═
C-- groups;(b) applying an N-hydroxysuccinimide-functionalized perfluorophenyl azide to a surface of the substrate to produce an NHS-PFPA-coated surface of the substrate; and (c) exposing the NHS-PFPA-coated surface to a reaction-energy source so as to cause the N-hydroxysuccinimide-functionalized perfluorophenyl azide to undergo nitrene addition to the reactive groups on the polymer molecules. - View Dependent Claims (22)
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25. A method for functionalizing surface molecules of a substrate, comprising:
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providing a substrate having chemical moieties each capable of undergoing an addition reaction with a nitrene; providing a first functionalizing reagent from a group consisting of functionalized perfluorophenyl azides according to the formula ##STR23## wherein X is selected from a group consisting of CN;
CONH2 ;
CHO;
CO2 CH3 ;
COCH3 ;
NO2 ;
CO2 H;
COCl;
CO-imidazole;
CONHS;
CH2 OH;
CH2 NH2 ;
COCH2 Br;
N-maleimido;
NH-biotinyl;
CONH--R, wherein R is a polypeptide;
CONH--X--S--S--Y--NH-biotinyl, wherein X and Y are spacer atoms; and
CONHS--SO3 Na;bringing the first functionalizing reagent into reactive proximity to the substrate molecules; and while the substrate molecules and the first functionalizing reagent are in reactive proximity, exposing the substance to a particle beam to convert the nitrenogenic groups to nitrenes that undergo addition reactions with the chemical moieties on the polymer molecules, thereby covalently bonding the first functionalizing reagent to preselected portions of the polymer molecules. - View Dependent Claims (26, 27, 28, 29)
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Specification