Separation of nanoparticles

A method of separation, filtration or purification of nano-materials comprising (a) transferring an aqueous solution or emulsion comprising a perylene supramolecular structure through porous solid support, thereby forming a noncovalent self-assembly perylene based membrane on said porous solid support;

• (b) transferring a solution of nano-materials through said noncovalent self-assembled perylene based membrane of step (a);
• wherein the particles size which are larger than the pores of said membrane remain on said membrane;
• wherein said noncovalent self-assembled perylene diimide comprises a perylene, a salt thereof or a metal thereof as a monomeric unit represented by the structure of formula I:
• wherein
• R1 and R1′ are independently [(CH2)nO]oCH3, [(CH2)nC(O)O]oCH3, [(CH2)nC(O)NH]oCH3, [(CH2)nCH2═CH2]oCH3, [(CH2)nCH≡CH]oCH3, [(CH2)nNH]oCH3, [(alkylene)nO]oCH3, [(alkylene)nC(O)O]oCH3, [(alkylene)nC(O)NH]oCH3, [(alkylene)nCH2═CH2]oCH3, [(alkylene)nCH≡CH]oCH3, [(alkylene)nNH]oCH3, (C1-C32)alkyl, (C3-C8)cycloalkyl, aryl, heteroaryl, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)NHR3NH]pH wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• wherein A comprises three same or different of the following substituents Cl, Br, I, O(C1-C8)alkyl or (C1-C8)alkyl;
• and wherein R3 in said [C(O)NHR3NH]pH is an alkyl, haloalkyl, hydroxyalkyl, hydroxyl, aryl, phenyl, alkylphenyl, alkylamino and independently the same or different when p is larger than 1;
• R2 and R2′ are independently [(CH2)qO]rCH3, [(CH2)qC(O)O]rCH3, [(CH2)qC(O)NH]rCH3, [(CH2)qCH2═CH2]rCH3, [(CH2)qCH≡CH]rCH3, [(CH2)qNH]rCH3, [(alkylene)qO]rCH3, [(alkylene)qC(O)O]rCH3, [(alkylene)qC(O)NH]rCH3, [(alkylene)qCH2═CH2]rCH3, [(alkylene)qCH≡CH]rCH3, [(alkylene)qNH]rCH3, (C1-C32)alkyl, (C3-C8)cycloalkyl, aryl, heteroaryl, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)NHR4NH]sH wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• wherein A comprises three same or different of the following substituents Cl, Br, I, O(C1-C8)alkyl or (C1-C8)alkyl;
• and wherein R4 in said [C(O)NHR4NH]sH is an alkyl, haloalkyl, hydroxyalkyl, hydroxyl, aryl, phenyl, alkylphenyl, alkylamino and independently the same or different when s is larger than 1;
• R5 and R5′ are independently H, —ORx where Rx is C1-C6 alkyl or [(CH2)qO]rCH3, [(CH2)qC(O)O]rCH3, [(CH2)qC(O)NH]rCH3, [(CH2)qCH2═CH2]rCH3, [(CH2)qCH≡CH]rCH3, [(CH2)qNH]rCH3, [(alkylene)qO]rCH3, [(alkylene)qC(O)O]rCH3, [(alkylene)qC(O)NH]rCH3, [(alkylene)qCH2═CH2]rCH3, [(alkylene)qCH≡CH]rCH3, [(alkylene)qNH]rCH3, aryl, heteroaryl, C≡C—R7, CH═CR8R9, NR10R11, amino acid, peptide or a saturated carbocyclic or heterocyclic ring wherein said saturated heterocyclic ring or heteroaryl contains at least one nitrogen atom and R5 or R5′ are connected via the nitrogen atom and wherein said saturated carbocyclic ring, heterocyclic ring, aryl and heteroaryl groups are optionally substituted by 1-3 groups selected from halide, aryl, heteroaryl, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• R7 is H, halo, (C1-C32)alkyl, aryl, NH2, alkyl-amino, COOH, C(O)H, alkyl-COOH heteroaryl, Si(H)3 or Si[(C1-C8)alkyl]3 wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups selected from halide, aryl, heteroaryl, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• R8, R9, R10 and R11 are independently H, (C1-C32)alkyl, aryl, NH2, alkyl-amino, COOH, C(O)H, alkyl-COOH or heteroaryl wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• L is a linker;
• n is an integer from 1-5;
• o is an integer from 1-100;
• p is an integer from 1-100;
• q is an integer from 1-5;
• r is an integer from 1-100;
• and
• s is an integer from 1-100;
• wherein if R5 and R5′ independently are amino acid or peptide;
• said membrane will form a chiral membrane.

A biocatalytic membrane comprising a noncovalent self-assembled porous membrane comprising a perylene diimide supramolecular structure and an enzyme;

• wherein said enzyme is immobilized within said membrane;
• wherein said noncovalent self-assembled perylene diimide comprises a perylene, a salt thereof or a metal thereof as a monomeric unit represented by the structure of formula I:
• wherein
• R1 and R1′ are independently [(CH2)nO]oCH3, [(CH2)nC(O)O]oCH3, [(CH2)nC(O)NH]oCH3, [(CH2)nCH2═CH2]oCH3, [(CH2)nCH≡CH]oCH3, [(CH2)nNH]oCH3, [(alkylene)nO]oCH3, [(alkylene)nC(O)O]oCH3, [(alkylene)nC(O)NH]oCH3, [(alkylene)nCH2═CH2]oCH3, [(alkylene)nCH≡CH]oCH3, [(alkylene)nNH]oCH3, (C1-C32)alkyl, (C3-C8)cycloalkyl, aryl, heteroaryl, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)NHR3NH]pH wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• wherein A comprises three same or different of the following substituents Cl, Br, I, O(C1-C8)alkyl or (C1-C8)alkyl;
• and wherein R3 in said [C(O)NHR3NH]pH is an alkyl, haloalkyl, hydroxyalkyl, hydroxyl, aryl, phenyl, alkylphenyl, alkylamino and independently the same or different when p is larger than 1;
• R2 and R2′ are independently [(CH2)qO]rCH3, [(CH2)qC(O)O]rCH3, [(CH2)qC(O)NH]rCH3, [(CH2)qCH2═CH2]rCH3, [(CH2)qCH≡CH]rCH3, [(CH2)qNH]rCH3, [(alkylene)qO]rCH3, [(alkylene)qC(O)O]rCH3, [(alkylene)qC(O)NH]rCH3, [(alkylene)qCH2═CH2]rCH3, [(alkylene)qCH≡CH]rCH3, [(alkylene)qNH]rCH3, (C1-C32)alkyl, (C3-C8)cycloalkyl, aryl, heteroaryl, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)NHR4NH]sH wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• wherein A comprises three same or different of the following substituents Cl, Br, I, O(C1-C8)alkyl or (C1-C8)alkyl;
• and wherein R4 in said [C(O)NHR4NH]sH is an alkyl, haloalkyl, hydroxyalkyl, hydroxyl, aryl, phenyl, alkylphenyl, alkylamino and independently the same or different when s is larger than 1;
• R5 and R5′ are independently H, —ORx where Rx is C1-C6 alkyl or [(CH2)qO]rCH3, [(CH2)qC(O)O]rCH3, [(CH2)qC(O)NH]rCH3, [(CH2)qCH2═CH2]rCH3, [(CH2)qCH≡CH]rCH3, [(CH2)qNH]rCH3, [(alkylene)qO]rCH3, [(alkylene)qC(O)O]rCH3, [(alkylene)qC(O)NH]rCH3, [(alkylene)qCH2═CH2]rCH3, [(alkylene)qCH≡CH]rCH3, [(alkylene)qNH]rCH3, aryl, heteroaryl, C≡C—R7, CH═CR8R9, NR10R11, amino acid, peptide or a saturated carbocyclic or heterocyclic ring wherein said saturated heterocyclic ring or heteroaryl contains at least one nitrogen atom and R5 or R5′ are connected via the nitrogen atom and wherein said saturated carbocyclic ring, heterocyclic ring, aryl and heteroaryl groups are optionally substituted by 1-3 groups selected from halide, aryl, heteroaryl, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• R7 is H, halo, (C1-C32)alkyl, aryl, NH2, alkyl-amino, COOH, C(O)H, alkyl-COOH heteroaryl, Si(H)3 or Si[(C1-C8)alkyl]3 wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups selected from halide, aryl, heteroaryl, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• R8, R9, R10 and R11 are independently H, (C1-C32)alkyl, aryl, NH2, alkyl-amino, COOH, C(O)H, alkyl-COOH or heteroaryl wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups selected from halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl), and O—(C1-C6 alkyl);
• L is a linker;
• n is an integer from 1-5;
• o is an integer from 1-100;
• p is an integer from 1-100;
• q is an integer from 1-5;
• r is an integer from 1-100;
• and
• s is an integer from 1-100;
• wherein if R5 and R5′ independently are amino acid or peptide;
• said membrane will form a chiral membrane.