Substrate with controlled amine density and regular spacing and method for preparing the same
OwnerJoon-Won Park, Jeo-Young Shim +2inventors
InventorsJoon-Won Park, Jeo-Young Shim, Joong-Ho Moon, Bong-Jin Hong
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Abstract
The present invention relates to a substrate useful to bio-chips comprising a molecular layer having low surface density of amines, and it provides a compound of Chemical Formula (1) represented by N—CBZ-[1]amine-[9]acid having a carboxylic acid, a substrate comprising a surface having a molecular layer prepared by reacting amine groups of aminosilylated surface of the substrates with a compound of Chemical Formula (1) having a cone shape, and methods for preparing the same.
Claims15
A compound represented by Chemical Formula 1:
- 9
- wherein R is phenyl;
- phenyl substituted with nitro, halogen or cyano group;
- naphthyl;
- or anthryl.
A preparation method of the carboxylic derivative represented by Chemical Formula 1, which comprises:
- 11
- wherein R is phenyl;
- phenyl substituted with nitro, halogen, or cyano group;
- naphthyl, or anthryl:
- a) a step of cyanoethylating tris(hydroxymethyl)aminomethane and acrylonitrile in order to prepare tris[(cyanoethoxy)methyl]aminomethane;
- b) a step of refluxing the mixture, after adding concentrated hydrochloric acid to the tris[(cyanoethoxy)methyl]aminomethane in order to prepare tris[(carboxyethoxy)ethyl]methyl]aminomethane;
- c) a step of esterificating the tris[(carboxyethoxy)ethyl]methyl]aminomethane by adding methanol to the tris[(carboxyethoxy)ethyl]methyl]aminomethane in order to prepare tris[((methoxycarbonyl)ethoxy)methyl]aminomethane;
- d) a step of protecting the tris[((methoxycarbonyl)ethoxy)methyl]aminomethane by adding a compound represented by Chemical Formula 2 to the tris[((methoxycarbonyl)ethoxy)methyl]aminomethane in order to prepare a compound represented by Chemical Formula 3:
- ROCOCI Chemical Formula 2]
- wherein R is phenyl;
- phenyl substituted with nitro, halogen or cyano group;
- naphthyl;
- or anthryl,
- 12
- wherein R is phenyl;
- phenyl substituted with nitro, halogen, or cyano group;
- naphthyl;
- or anthryl;
- e) a step of hydrolyzing the mixture after adding sodium hydroxide solution to the compound represented by Chemical Formula 3 in order to prepare a compound represented by Chemical Formula 4:
- 13
- wherein R is phenyl;
- phenyl substituted with nitro, halogen or cyano group;
- naphthyl;
- or anthryl;
- f) a step of reacting the mixture after dissolving the compound represented by Chemical Formula 4 and the tris[((methoxycarbonyl)ethoxy)methyl]aminomethane in dimethylformamide (DMF) and adding dicyclohexylcarbodiimide and hydroxybenzotriazole to the dissolved material to prepare a compound represented by Chemical Formula 5:
- 14
- wherein R is phenyl;
- phenyl substituted with nitro, halogen, or cyano group;
- naphthyl;
- or anthryl;
- and
- g) a step of hydrolyzing the mixture after adding sodium hydroxide solution to the compound represented by Chemical Formula 5 in order to prepare the compound represented by Chemical Formula 1.
A substrate comprising a molecular layer prepared by reacting amine groups on the surface of an aminosilylated substrate with a cone-shaped carboxylic derivative represented by Chemical Formula 1 on the substrate surface:
- 15
- wherein R is phenyl;
- phenyl substituted with nitro, halogen, or cyano group;
- naphthyl;
- or anthryl.
A preparation method of a substrate comprising a molecular layer with a controlled amine density and regular spacing, which comprises:
- a) a step of preparing a substrate comprising a molecular layer of aminosilane on the substrate surface;
- and
- b) a step of reacting the amine of the molecular layer with a carboxylic derivative.
Dependencies are inferred from the claim text.