Methods for the synthesis of modular poly(phenyleneethynylenes) and fine tuning the electronic properties thereof for the functionalization of nanomaterials
AssigneeZyvex Performance Materials, LLC
InventorsHassan Ait-Haddou, Marni Rutkofsky
Life of this patent
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Abstract
Poly(aryleneethynylene) polymers for exfoliating and dispersing/solubilizing nanomaterial are provided herein. The poly(aryleneethynylene) polymers have unit monomer portions, each monomer portion having at least one electron donating substituent thereby forming an electron donor monomer portion, or at least one electron withdrawing substituent thereby forming an electron accepting monomer portion. Such polymers exfoliate and disperse nanomaterial without presonication of the nanomaterial.
Claims5
A composition for functionalizing nanomaterials comprising a poly(phenyleneethynylene) polymer having the following structure:
- wherein
- a+b+c is from about 20 to about 190;
- X1, X2, Y1 and Y2 are independently selected from the group consisting of CO, COO, CONN, CONHCO, COOCO, CONHCNH, CON, COS, CS, alkyl, aryl, allyl, N, NO, S, O, CN, CNN, SO, SO2, P and PO;
- R1—R6 are independently selected from the group consisting of alkyl, phenyl, benzyl, aryl, allyl, or hydrogen;
- wherein:
- when X1, X2, Y1 or Y2 is CO, COO, CONN, CONHCO, COOCO, CONHCNH, CON, COS, CS, CN, CNN, SO, SO2, NO or PO then X1R1, X2R2, Y1R3, Y2R4, X1R5 or X2R6 is an electron withdrawing substituent;
- and
- when X1, X2, Y1 or Y2 is alkyl, aryl, allyl, N, S, O or P then X1R1, X2R2, Y1R3, Y2R4, X1R5 or X2R6 is an electron donating substituent;
- and
- Z is COOR, wherein R is alkyl, aryl, allyl, phenyl, or benzyl.
A composition for functionalizing nanomaterials comprising a poly(phenyleneethynylene) polymer having the following structure:
- wherein
- a+b+c is from about 20 to about 190;
- X1, X2, Y1 and Y2 are independently selected from the group consisting of CO, COO, CONH, CONHCO, COOCO, CONHCNH, CON, COS, CS, alkyl, aryl, allyl, N, NO, S, O, CN, CNN, SO, SO2, P and PO;
- R1—R6 are independently selected from the group consisting of alkyl, phenyl, benzyl, aryl, allyl, or hydrogen;
- wherein:
- when X1, X2, Y1 or Y2 is CO, COO, CONH, CONHCO, COOCO, CONHCNH, CON, COS, CS, CN, CNN, SO, SO2, NO or PO then X1R1, X2R2, Y1R3, Y2R4, X1R5 or X2R6 is an electron withdrawing substituent;
- and
- when X1, X2, Y1 or Y2 is alkyl, aryl, allyl, N, S, O or P then X1R1, X2R2, Y1R3, Y2R4, X1R5 or X2R6 is an electron donating substituent;
- and
- Z is independently OH, SH, COOH, COOR, CHO, NH2, CO-alkoxyalkyl, CO-alkylamine, CO-arylamine, CO-alkylhydroxy, CO-arylhydroxy, CO-antibiotic, NH2-antibiotic, CO-sugar, sugar-OH, CO-dendrimer, CO-dendron, NH2-dendrimer, NH2-dendron, CO-protein, NH2-protein, CO-melamine, CO-epoxy, CO-diamine, CO-alkyl, CO-crown ether, CO-ethylene glycol, CO-polyamine, CO-DNA, CO—RNA, polyethoxyalkyl, polypropoxyalkyl, aziridine group, olefin, NHR, COR, CNR, CN, CONH2, CONHR, lipid, ligand for metal complexation, ligand for biomolecule complexation, an epoxy group, a styrene unit, an acrylate unit, or a combination thereof, wherein R of COOR is alkyl, aryl, allyl, phenyl, or benzyl.
A composition for functionalizing nanomaterials comprising a poly(phenyleneethynylene) polymer having the following structure:
- wherein
- a+b+c is from about 20 to about 190;
- X1, X2, Y1 and Y2 are independently selected from the group consisting of CO, COO, CONH, CONHCO, COOCO, CONHCNH, CON, COS, CS, alkyl, aryl, allyl, N, NO, S, O, CN, CNN, SO, SO2, P and PO;
- and
- R1—R6 are independently selected from the group consisting of alkyl, phenyl, benzyl, aryl, allyl, or hydrogen;
- wherein:
- when X1, X2, Y1 or Y2 is CO, COO, CONH, CONHCO, COOCO, CONHCNH, CON, COS, CS, CN, CNN, SO, SO2, NO or PO then X1R1, X2R2, Y1R3, Y2R4, X1R5 or X2R6 is an electron withdrawing substituent;
- and
- when X1, X2, Y1 or Y2 is alkyl, aryl, allyl, N, S, O or P then X1R1, X2R2, Y1R3, Y2R4, X1R5 or X2R6 is an electron donating substituent.
Dependencies are inferred from the claim text.