Separation of nanoparticles

Noncovalent self-assembled porous membrane comprising a perylene diimide supramolecular structure, which provides a chromatography medium for size-selective separation of nano-material;

• wherein said perylene diimide supramolecular structure comprises a mixture of perylene diimide compounds, wherein each perylene diimide compound is a monomeric unit represented by the structure of formula I:
• wherein
• R1 and R1′ are each independently [(CH2)qO]rCH3, [(CH2)qO]rH [(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, chiral group, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)CHR3NH]pH wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups comprising halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl) or 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)CHR3NH]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 each 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, chiral group, (C1-C32)alkyl-COOH, (C1-C32)alkyl-Si-A, or [C(O)CHR3NH]pH wherein said aryl or heteroaryl groups are optionally substituted by 1-3 groups comprising halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl) or 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)CHR4NH]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 each independently R5 and R5′ are each independently H, —ORx where Rx is C1-C6 alkyl, [(CH2)nO]oCH3 or [(CH2)nO]oH;
• [(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, aryl, heteroaryl, C≡C—R7, CH═CR8R9, NR10R11, chiral group, 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 comprising halide, aryl, heteroaryl, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl) or 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 comprising halide, aryl, heteroaryl, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl) or O—(C1-C6 alkyl);
• R8, R9, R10 and R11 are each 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 comprising halide, CN, CO2H, OH, SH, NH2, CO2—(C1-C6 alkyl) or O—(C1-C6 alkyl);
• L diethynyldipyridine group;
• 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/or R5′ are chiral;
• said membrane will form a chiral membrane;
• wherein said mixture comprises between 2 to 10 different perylene diimide compounds of formula I;
• wherein if R1, R1′, R2 and R2′ are isopentyl and both R5 and R5′ are [(CH2)nO]oCH3] and n is 2, then o is different for each compound and o is between 15-20 or 30-60.