IP Library Granted Patent US 12,104,106
Granted Patent B2
US 12,104,106 · App. 17/360,064 · Granted Oct 1, 2024

Compositions of chiral molecules and perovskite nanocrystals and methods of making the same

Inventors: Joseph Matthew Luther (Boulder, CO); Matthew Craig Beard (Arvada, CO); Young-Hoon Kim (Lakewood, CO)
Assignee: Alliance for Sustainable Energy, LLC
C09K11/664C07F7/24C09K11/025C09K11/665H01F10/3259H10N50/80G02B1/08H10K30/10
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Quick Facts
Patent No.
US 12,104,106
App. No.
17/360,064
Granted
Oct 1, 2024
Kind
B2
Abstract

The present disclosure relates to a composition that includes a nanocrystalline core that includes a perovskite and having an outer surface, and a chiral molecule having a functional group, where the functional group is bonded to a first portion of the outer surface, and the composition is capable of circularly polarized luminescence (CPL). In some embodiments of the present disclosure, the composition is capable of absorbing circularly-polarized light.

Claims (29)

1. A composition comprising:

a nanocrystalline core comprising a perovskite having an outer surface;

a chiral molecule comprising a functional group and a second group; and

a halide, wherein:

the perovskite comprises at least one of FAPb(X y X′ z X″ 1−y−z ) 3 , CsPb(X y X′ z X″ 1−y−z ) 3 , MAPb(X y X′ z X″ 1−y−z ) 3 , or Cs 1−u−v MA u FA v Pb(X y X′ z X″ 1−y−z ) 3 ,

X comprises at least one of iodide, bromide, or chloride,

X′ comprises at least one of iodide, bromide, or chloride and is different than X,

X″ comprises at least one of iodide, bromide, or chloride and is different than X and X′,

0≤z≤1, 0≤y≤1, 0≤u≤1, 0≤v≤1,

the functional group comprises an amine group,

the second group comprises a hydrocarbon having between 3 and 30 carbon atoms,

the functional group is bonded to a first portion of the outer surface,

the halide interacts with at least one of the outer surface or with the chiral molecule, and

the composition is capable of circularly polarized luminescence (CPL).

2. The composition of claim 1 , wherein the nanocrystalline core has a characteristic length between about 1 nm and about 1000 nm.

3. The composition of claim 1 , wherein the CPL has an average luminescence dissymmetry g-factor between about 1.0 and about 0.0001 in a wavelength range between about 400 nm and about 1000 nm.

4. The composition of claim 1 , wherein the chiral molecule is present on the outer surface at a concentration between about 1 molecule/nm 2 and about 10 molecules/nm 2 .

5. The composition of claim 1 , wherein the second group comprises a hydrocarbon comprising at least one of a straight chained functional group, a branched functional group, or a ringed functional group.

6. The composition of claim 1 , wherein the halide comprises at least one of bromide, chloride, or iodide.

7. The composition of claim 1 , wherein the nanocrystalline core has a shape comprising at least one of a cube, a rod, a wire, or a plate.

8. The composition of claim 1 , wherein the chiral molecule comprises at least one of (R)-2-octylamine, (S)-2-octylamine, R-methylbenzylammonium, S-methylbenzyleammonium, R-cysteine, S-cysteine, L-canavanine, L-canavanine sulfate salt, L-leucine, L-proline, N-acetyl-D-penicillamine, L-cysteine hydrochloride monohydrate, (R)-(−)-sec-butylamine, (S)-(+)-sec-butylamine, (R)-(−)-2-amino-3-methylbutane, (S)-(+)-2-amino-3-methylbutane, (S)-(+)-3,3-dimethyl-2-butylamine, (R)-(−)-3,3-dimethyl-2-butylamine, (S)-(+)-1-cyclohexylethylamine, (R)-(−)-1-cyclohexylethylamine, R-ethylbenzylamine, S-ethylbenzylamine, sulfobetaine, phosphocholine, (S)-(−)-1-(1-naphthyl)ethylamine, (S)-(+)-1,2,3,4-tetrahydro-1-naphthylamine, (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, (S)-(+)-3-amino-1-boc-piperidine, (S)-(−)-1-(4-bromophenyl)ethylamine, (S)-(+)-1-aminoindan, (S)-1-cyclopropylethylamine, (S)-(−)-3-cyclohexene-1-carboxylic acid, (S)-(−)-1-(2-naphthyl)ethylamine, (S)-1-(2-fluorophenyl)ethylamine, (S)-(−)-1-amino-2-(methoxymethyl)pyrrolidine, (R)-(+)-bornylamine, (S)-1-m-tolylethanamine, (S)-(+)-1-methoxy-2-propylamine, (S)-(+)-1-methyl-3-phenylpropylamine, (S)-(+)-1-amino-2-propanol, (S)-1,4-benzodioxane-2-carboxylic acid, (S)-1,2,3,4-tetrahydro-1-naphthoic acid, (R)-1,2,3,4-tetrahydro-1-naphthoic acid, (R)-(−)-1,2,3,4-tetrahydro-1-naphthylamine, (R)-(+)-1,2-dithiolane-3-pentanoic acid, (S)-1-boc-4-oxopiperidine-2-carboxylic acid, penicillamine, glutathione, oligopeptide, or L-cystathionine.

9. The composition of claim 1 , further comprising:

a non-chiral molecule, wherein:

the non-chiral molecule is bonded to a second portion of the outer surface.

10. The composition of claim 9 , wherein the non-chiral molecule is present on the outer surface at a concentration between about 1 molecule/nm 2 and about 10 molecules/nm 2 .

11. The composition of claim 9 , wherein the non-chiral molecule comprises at least one of oleylammonium, oleate, a zwitterion, an alkyl halide, a primary alcohol, a secondary alcohol, a tertiary alcohol, an alkylamine, a p-substituted aniline, a phenyl ammonium, a fluorine ammonium, a carboxylic acid, acetic acid, 5-aminosalicylic acid, acrylic acid, L-aspentic acid, 6-bromohexanoic acid, bromoacetic acid, dichloroacetic acid, ethylenediaminetetraacetic acid, isobutyric acid, itaconic acid, maleic acid, r-maleimidobutyric acid, L-malic acid, 4-nitrobenzoic acid, 1-pyrenecarboxylic acid, or oleic acid.

12. The composition of claim 11 , wherein the alkyl halide comprises an acyclic alkyl having a structure of C n H 2n+1 .

13. The composition of claim 11 , wherein the carboxylic acid comprises 4,4′-azobis(4-cyanovaleric acid).

14. The composition of claim 11 , wherein the zwitterion comprises sulfobetaine.

Assignments (3)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
CONFIRMATORY LICENSE Recorded Mar 30, 2022
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 059447/0656 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2021
From: LUTHER, JOSEPH MATTHEW; BEARD, MATTHEW CRAIG; KIM, YOUNG-HOON
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 056686/0701 →