Thermally stable polythiol ligands with pendant solubilizing moieties
AssigneeShoei Chemical Inc.
InventorsDavid Olmeijer, Ravisubhash Tangirala, Austin Smith
Life of this patent
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Abstract
The present invention provides nanostructure compositions and methods of producing nanostructure compositions. The nanostructure compositions comprise a population of nanostructures comprising polythiol ligands with pendant moieties. The polythiol ligand with pendant moieties increase the solubility of the nanostructures in solvents and resins. The present invention also provides nanostructure films comprising the nanostructure compositions and methods of making nanostructure films using the nanostructure compositions.
Claims16
A nanostructure composition comprising:
- (a) a nanostructure;
- and
- (b) polythiol ligands dispersed on the surface of the nanostructure, the polythiol ligands having the formula I:
- wherein:
- CM is a central moiety, wherein CM is selected from the group consisting of an alkane, a 1,3,5-triazine, a pentaerythritol, a 1,3,5-triazine-2,4,6-trione, a trimethylolpropane, and a (propane-2,2-diylbis(4,1-phenylene))bis(λ′-oxy);
- X1 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X2 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X3 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X4 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X5 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X6 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- B is —CH2—CH2—C(═O)—O—, —CH2—C(CH3)2—C(═O)—O—, —CH2—CH(CH3)—C(═O)—NH—, —C(═O)—NH—, —CH2—CH2—, or —CH2—CH(OH)—CH2—O—;
- X7 is a bond or C1-12 alkylene;
- X8 is a bond, —O—, —C(═O)—O—, or —C(═O)—N—;
- R1A and R1B independently are H or C1-20 alkyl;
- R2 is C1-20 alkyl or C1-20 alkoxy;
- a is 2 to 10;
- b is 0 to 10;
- c is 2 to 10;
- d is 0 to 10;
- e is 1 to 100;
- and
- f is 0 to 100;
- wherein a+b+c+d has a value within a range of 4 to 40.
A method of replacing a first ligand on a nanostructure with a second ligand comprising admixing a reaction mixture comprising a population of nanostructures having a first ligand non-covalently bound to the nanostructure and a second ligand which is a polythiol ligand, such that the second ligand displaces the first ligand and becomes non-covalently bound to the nanostructure, wherein the polythiol ligand has formula I:
- wherein:
- CM is a central moiety, wherein CM is selected from the group consisting of an alkane, a 1,3,5-triazine, a pentaerythritol, a 1,3,5-triazine-2,4,6-trione, a trimethylolpropane, and a (propane-2,2-diylbis(4,1-phenylene))bis(λ′-oxy);
- X1 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X2 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X3 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X4 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X5 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X6 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- B is —CH2—CH2—C(═O)—O—, —CH2—C(CH3)2—C(═O)—O—, —CH2—CH(CH3)—C(═O)—NH—, —C(═O)—NH—, —CH2—CH2—, or —CH2—CH(OH)—CH2—O—;
- X7 is a bond or C1-12 alkylene;
- X8 is a bond, —O—, —C(═O)—O—, or —C(═O)—N—;
- R1A and R1B independently are H or C1-20 alkyl;
- R2 is C1-20 alkyl or C1-20 alkoxy;
- a is 2 to 10;
- b is 0 to 10;
- c is 2 to 10;
- d is 0 to 10;
- e is 1 to 100;
- and
- f is 0 to 100;
- wherein a+b+c+d has a value within a range of 4 to 40.
A nanostructure film layer comprising:
- (a) a nanostructure;
- (b) polythiol ligands dispersed on the surface of the nanostructure, the polythiol ligands having the formula I:
- wherein:
- CM is a central moiety, wherein CM is selected from the group consisting of an alkane, a 1,3,5-triazine, a pentaerythritol, a 1,3,5-triazine-2,4,6-trione, a trimethylolpropane, and a (propane-2,2-diylbis(4,1-phenylene))bis(λ′-oxy);
- X1 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X2 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X3 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X4 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X5 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- X6 is a bond, —C(═O)—, a C1-10 alkylene, or a C2-10 heteroalkylene;
- B is —CH2—CH2—C(═O)—O—, —CH2—C(CH3)2—C(═O)—O—, —CH2—CH(CH3)—C(═O)—NH—, —C(═O)—NH—, —CH2—CH2—, or —CH2—CH(OH)—CH2—O—;
- X7 is a bond or C1-12 alkylene;
- X8 is a bond, —O—, —C(═O)—O—, or —C(═O)—N—;
- R1A and R1B independently are H or C1-20 alkyl;
- R2 is C1-20 alkyl or C1-20 alkoxy;
- a is 2 to 10;
- b is 0 to 10;
- c is 2 to 10;
- d is 0 to 10;
- e is 1 to 100;
- and
- f is 0 to 100;
- wherein a+b+c+has a value within a range of 4 to 40;
- and
- (c) at least one organic resin.
Dependencies are inferred from the claim text.