Semiconductor nanocrystal composite

A waveguide comprising a plurality of layers, at least one layer containing a first semiconductor nanocrystal in a first metal oxide matrix and a coordinating ligand associated with the semiconductor nanocrystal;

• wherein the coordinating ligand has the formula
• wherein k is 2, 3 or 5, n is 1, 2, 3, 4 or 5, and m is 1 or 2, 3, 4, 5, 6, 7, 8, 9 or 10;
• X is O, S, S═O, SO2, Se, Se═O, N, N═O, P, P═O, As, or As═O;
• each of Y and L, independently, is a straight or branched C2−12 hydrocarbon chain optionally containing at least one double bond, at least one triple bond, or at least one double bond and one triple bond, the hydrocarbon chain being optionally substituted with one or more C1−4 alkyl, C2−4 alkenyl, C2−4 alkynyl, C1−4 alkoxy, hydroxyl, halo, amino, nitro, cyano, C3−5 cycloalkyl, 3−5 membered heterocycloalkyl, monocyclic aryl, 5−6 membered heteroaryl, C1−4 alkylcarbonyloxy, C1−4 alkyloxycarbonyl, C1−4 alkylcarbonyl, or formyl and the hydrocarbon chain being optionally interrupted by -O-, -S-, -N(Re)-C(O)-O-, -O-C(O)-N(Re)-, -N(Re)-C(O)-N(Rf)-, -O-C(O)-O-, -P(Re)-, or -P(O)(Re)-;
• each of Re and Rf, independently, is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylakyl, hydroxyl, or haloalkyl;
• and
• Z is hydroxy, sulfhydryl, sulfinate, sulfinic acid, sulfonate, sulfonic acid, disulphide, carboxyl, carboxylate, amine, amide, alkoxysilyl, halosilyl, phosphate, phosphonic acid, phosphonate ester, phosphinate, phosphinic acid, or phosphinate ester.

A method of manufacturing a composite comprising:

• providing a semiconductor nanocrystal;
• providing a matrix precursor;
• contacting the semiconductor nanocrystal with a coordinating ligand that includes a moiety that is compatible with, soluble within, or reacts with a matrix;
• and
• forming a solid including titanium from the precursor and the semiconductor nanocrystal;
• wherein the coordinating ligand has the formula
• wherein k is 2, 3 or 5, n is 1, 2, 3, 4 or 5, and m is 1 or 2, 3, 4, 5, 6, 7, 8, 9 or 10;
• X is O, S, S═O, SO2, Se, Se═O, N, N═O, P, P═O, As, or As═O;
• each of Y and L, independently, is a straight or branched C2−12 hydrocarbon chain optionally containing at least one double bond, at least one triple bond, or at least one double bond and one triple bond, the hydrocarbon chain being optionally substituted with one or more C1−4 alkyl, C2−4 alkenyl, C2−4 alkynyl, C1−4 alkoxy, hydroxyl, halo, amino, nitro, cyano, C3−5 cycloalkyl, 3−5 membered heterocycloalkyl, monocyclic aryl, 5−6 membered heteroaryl, C1−4 alkylcarbonyloxy, C1−4 alkyloxycarbonyl, C1−4 alkylcarbonyl, or formyl and the hydrocarbon chain being optionally interrupted by -O-, -S-, -N(Re)-, -N(Re)-C(O)-O-, -O-C(O)-N(Re)-, -N(Re)-C(O)-N(Rf)-, -O-C(O)-O-, -P(Re)-, or -P(O)(Re)-;
• each of Re and Rf, independently, is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylakyl, hydroxyl, or haloalkyl;
• and
• Z is hydroxy, sulfhydryl, sulfinate, sulfinic acid, sulfonate, sulfonic acid, disulphide, carboxyl, carboxylate, amine, amide, alkoxysilyl, halosilyl, phosphate, phosphonic acid, phosphonate ester, phosphinate, phosphinic acid, or phosphinate ester.

A composite comprising:

• a plurality of semiconductor nanocrystals in an inorganic matrix, wherein a semiconductor nanocrystal of the plurality includes a core including a first semiconductor material and an overcoating including a second semiconductor material on a surface of the core;
• and
• a coordinating ligand associated with the semiconductor nanocrystal;
• wherein the coordinating ligand has the formula
• wherein k is 2, 3 or 5, n is 1, 2, 3, 4 or 5, and m is 1 or 2, 3, 4, 5, 6, 7, 8, 9 or 10;
• X is O, S, S═O, SO2, Se, Se═O, N, N═O, P, P═O, As, or As═O;
• each of Y and L, independently, is a straight or branched C2−12 hydrocarbon chain optionally containing at least one double bond, at least one triple bond, or at least one double bond and one triple bond, the hydrocarbon chain being optionally substituted with one or more C1−4 alkyl, C2−4 alkenyl, C2−4 alkynyl, C1−4 alkoxy, hydroxyl, halo, amino, nitro, cyano, C3−5cycloalkyl, 3−5 membered heterocycloalkyl, monocyclic aryl, 5−6 membered heteroaryl, C1−4 alkylcarbonyloxy, C1−4 alkyloxycarbonyl, C1−4 alkylcarbonyl, or formyl and the hydrocarbon chain being optionally interrupted by -O-, -S-, -N(R+°)-, -N(Re)-C(O)-O-, -O-C(O)-N(Re)-, -N(Re)-C(O)-N(Rf)-, -O-C(O)-O-, -P(Re)-, or -P(O)(Re)-;
• each of Re and Rf, independently, is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylakyl, hydroxyl, or haloalkyl;
• and
• Z is hydroxy, sulfhydryl, sulfinate, sulfinic acid, sulfonate, sulfonic acid, disulphide, carboxyl, carboxylate, amine, amide, alkoxysilyl, halosilyl, phosphate, phosphonic acid, phosphonate ester, phosphinate, phosphinic acid, or phosphinate ester.

A waveguide comprising a plurality of layers, at least one layer containing a first semiconductor nanocrystal in a first metal oxide matrix and a coordinating ligand associated with the first semiconductor nanocrystal, wherein the first semiconductor nanocrystal includes a core including a first semiconductor material and an overcoating including a second semiconductor material on a surface of the core;

• wherein the coordinating ligand has the formula
• wherein k is 2,3 or 5, n is 1, 2, 3, 4 or 5, and m is 1 or 2, 3, 4, 5, 6, 7, 8, 9 or 10;
• X is O, S, S═O, SO2, Se, Se═O, N, N═O, P, P═O, As, or As═O;
• each of Y and L, independently, is a straight or branched C2−12 hydrocarbon chain optionally containing at least one double bond, at least one triple bond, or at least one double bond and one triple bond, the hydrocarbon chain being optionally substituted with one or more C1−4 alkyl, C2−4 alkenyl, C2−4 alkynyl, C1−4 alkoxy, hydroxyl, halo, amino, nitro, cyano, C3−5cycloalkyl, 3−5 membered heterocycloalkyl, monocyclic aryl, 5−6 membered heteroaryl, C1−4 alkylcarbonyloxy, C1−4 alkyloxycarbonyl, C1−4 alkylcarbonyl, or formyl and the hydrocarbon chain being optionally interrupted by -O-, -S-, -N(Re)-C(O)-O-, -O-C(O)-N(Re)-, -N(Re)-C(O)-N(Rf)-, -O-C(O)-O-, -P(Re)-, or -P(O)(Re)-;
• each of Re and Rf, independently, is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylakyl, hydroxyl, or haloalkyl;
• and
• Z is hydroxy, sulfhydryl, sulfinate, sulfinic acid, sulfonate, sulfonic acid, disulphide, carboxyl, carboxylate, amine, amide, alkoxysilyl, halosilyl, phosphate, phosphonic acid, phosphonate ester, phosphinate, phosphinic acid, or phosphinate ester.

A method of manufacturing a composite comprising:

• providing a semiconductor nanocrystal including a core including a first semiconductor material and an overcoating including a second semiconductor material on a surface of the core;
• providing a matrix precursor;
• contacting the semiconductor nanocrystal with a coordinating ligand that includes a moiety that is compatible with, soluble within, or reacts with a matrix;
• contacting the semiconductor nanocrystal with a precursor of the matrix;
• and
• forming a solid from the precursor and the semiconductor nanocrystal;
• wherein the coordinating ligand has the formula
• wherein k is 2, 3 or 5, n is 1, 2, 3, 4 or 5, and m is 1 or 2, 3, 4, 5, 6, 7, 8, 9 or 10;
• X is O, S, S═O, SO2, Se, Se═O, N, N═O, P, P═O, As, or As═O;
• each of Y and L, independently, is a straight or branched C2−12 hydrocarbon chain optionally containing at least one double bond, at least one triple bond, or at least one double bond and one triple bond, the hydrocarbon chain being optionally substituted with one or more C1−4 alkyl, C2−4 alkenyl, C2−4 alkynyl, C1−4 alkoxy, hydroxyl, halo, amino, nitro, cyano, C3−5cycloalkyl, 3−5 membered heterocycloalkyl, monocyclic aryl, 5−6 membered heteroaryl, C1−4 alkylcarbonyloxy, C1−4 alkyloxycarbonyl, C1−4 alkylcarbonyl, or formyl and the hydrocarbon chain being optionally interrupted by -O-, -S-, -N(Re)-, -N(Re)-C(O)-O-, -O-C(O)-N(Re)-, -N(Re)-C(O)-N(Rf)-, -O-C(O)-O-, -P(Re)-, or -P(O)(Re)-;
• each of Re and Rf, independently, is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylakyl, hydroxyl, or haloalkyl;
• and
• Z is hydroxy, sulfhydryl, sulfinate, sulfinic acid, sulfonate, sulfonic acid, disulphide, carboxyl, carboxylate, amine, amide, alkoxysilyl, halosilyl, phosphate, phosphonic acid, phosphonate ester, phosphinate, phosphinic acid, or phosphinate ester.

A method of manufacturing a composite comprising:

• providing a semiconductor nanocrystal;
• providing a matrix precursor;
• contacting the semiconductor nanocrystal with a coordinating ligand that includes a moiety that is compatible with, soluble within, or reacts with a matrix;
• contacting the semiconductor nanocrystal with a precursor of the matrix;
• and
• forming a solid from the precursor and the semiconductor nanocrystal;
• wherein the precursor is a metal halide or a metal alkoxide;
• wherein the coordinating ligand has the formula
• wherein k is 2, 3 or 5, n is 1, 2, 3, 4 or 5, and m is 1 or 2, 3, 4, 5, 6, 7, 8, 9 or 10;
• X is O, S, S═O, SO2, Se, Se═O, N, N═O, P, P═O, As, or As═O;
• each of Y and L, independently, is a straight or branched C2−12 hydrocarbon chain optionally containing at least one double bond, at least one triple bond, or at least one double bond and one triple bond, the hydrocarbon chain being optionally substituted with one or more C1−4 alkyl, C2−4 alkenyl, C2−4 alkynyl, C1−4 alkoxy, hydroxyl, halo, amino, nitro, cyano, C3−5cycloalkyl, 3−5 membered heterocycloalkyl, monocyclic aryl, 5−6 membered heteroaryl, C1−4 alkylcarbonyloxy, C1−4 alkyloxycarbonyl, C1−4 alkylcarbonyl, or formyl and the hydrocarbon chain being optionally interrupted by -O-, -S-, -N(Re)-, -N(Re)-C(O)-O-, -O-C(O)-N(Re)-, -N(Re)-C(O)-N(Rf)-, -O-C(O)-O-, -P(Re)-, or -P(O)(Re)-;
• each of Re and Rf, independently, is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylakyl, hydroxyl, or haloalkyl;
• and
• Z is hydroxy, sulfhydryl, sulfinate, sulfinic acid, sulfonate, sulfonic acid, disulphide, carboxyl, carboxylate, amine, amide, alkoxysilyl, halosilyl, phosphate, phosphonic acid, phosphonate ester, phosphinate, phosphinic acid, or phosphinate ester.

A method of manufacturing a composite comprising:

• providing a semiconductor nanocrystal;
• providing a matrix precursor;
• contacting the semiconductor nanocrystal with a coordinating ligand that includes a moiety that is compatible with, soluble within, or reacts with a matrix;
• contacting the semiconductor nanocrystal with a precursor of the matrix;
• and
• forming a solid from the precursor and the semiconductor nanocrystal;
• wherein the precursor is a titanium alkoxide, an aluminum alkoxide, a silicon alkoxide, a magnesium alkoxide, a boron alkoxide, a phosphorous alkoxide, a germanium alkoxide, an indium alkoxide, a tin alkoxide, a zirconium alkoxide, or a mixture thereof;
• wherein the coordinating ligand has the formula
• wherein k is 2, 3 or 5, n is 1, 2, 3, 4 or 5, and m is 1 or 2, 3, 4, 5, 6, 7, 8, 9 or 10;
• X is O, S, S═O, SO2, Se, Se═O, N, N═O, P, P═O, As, or As═O;
• each of Y and L, independently, is a straight or branched C2−12 hydrocarbon chain optionally containing at least one double bond, at least one triple bond, or at least one double bond and one triple bond, the hydrocarbon chain being optionally substituted with one or more C1−4 alkyl, C2−4 alkenyl, C2−4 alkynyl, C1−4 alkoxy, hydroxyl, halo, amino, nitro, cyano, C3−5cycloalkyl, 3−5 membered heterocycloalkyl, monocyclic aryl, 5−6 membered heteroaryl, C1−4 alkylcarbonyloxy, C1−4 alkyloxycarbonyl, C1−4 alkylcarbonyl, or formyl and the hydrocarbon chain being optionally interrupted by -O-, -S-, -N(Re)-, -N(Re)-C(O)-O-, -O-C(O)-N(Re)-, -N(Re)-C(O)-N(Rf)-, -O-C(O)-O-, -P(Re)-, or -P(O)(Re)-;
• each of Re and Rf, independently, is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, hydroxylakyl, hydroxyl, or haloalkyl;
• and
• Z is hydroxy, sulfhydryl, sulfinate, sulfinic acid, sulfonate, sulfonic acid, disulphide, carboxyl, carboxylate, amine, amide, alkoxysilyl, halosilyl, phosphate, phosphonic acid, phosphonate ester, phosphinate, phosphinic acid, or phosphinate ester.