IP Library Granted Patent US 12,365,830
Granted Patent B2
US 12,365,830 · App. 17/615,139 · Granted Jul 22, 2025

Ligand-exchangeable janus nanoparticles and methods of making the same

Inventors: Matthew Craig Beard (Arvada, CO); Marissa Sally Martinez (Wheat Ridge, CO); Zhiyuan Huang (Lakewood, CO)
Assignee: Alliance for Sustainable Energy, LLC
C09K11/025C07C57/60C09K11/661B82Y20/00B82Y40/00C07B2200/13
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,365,830
App. No.
17/615,139
Granted
Jul 22, 2025
Kind
B2
Abstract

The present disclosure relates to a nanocrystal that includes a nanocrystal core, a first ligand coordinated to a first portion of a surface of the nanocrystal core, and a second ligand coordinated to a second portion of the surface, where the second ligand includes a first functionalized aromatic molecule.

Claims (33)

1. A nanocrystal comprising:

a nanocrystal core comprising a mixed alloy; and

a Janus ligand shell comprising a first ligand coordinated to a first portion of a surface of the nanocrystal core and a second ligand coordinated to a second portion of the surface, wherein:

the first ligand comprises at least one of an alkyl carboxylate, an alkyl phosphonate, an alkyl thiolate, or a combination thereof, and

the second ligand is different than the first ligand.

2. The nanocrystal of claim 1 , wherein the second ligand comprises at least one of cinnamate, a functionalized cinnamate, or a combination thereof.

3. The nanocrystal of claim 2 , wherein the functionalized cinnamate comprises a carboxylate of at least one of 2,3,4,5,6-pentafluorocinnamic acid, 3,5-bis(trifluoromethyl) cinnamic acid, 4-(2,2-dicyanovinyl) cinnamic acid, 4-nitrocinnamic acid, 4-cyanocinnamic acid, 3,5-difluoro-4-trifluoromethyl cinnamic acid, 4-formylcinnamic acid, 4-trifluoromethylcinnamic acid, 3,5-difluorocinnamic acid, 4-chlorocinnamic acid, 4-bromocinnamic acid, 4-iodocinnamic acid, 4-fluorocinnamic acid, cinnamic acid, 4-mercaptocinnamic acid, 4-carboxycinnamic acid, 4-hydroxycinnamic acid, 3,5-dimethoxy-4-hydroxycinnamic acid, 4-methylcinnamic acid, 4-ethylcinnamic acid, 4-tertbutylcinnamic acid, 2,6-difluorocinnamic acid, 4-methoxycinnamic acid, 2,6-difluoro-4-methoxycinnamic acid, 4-dimethylaminocinnamic acid, 4-aminocinnamic acid, alpha-cyano-4-dimethylaminocinnamic acid, 4-(di-(4-methoxyphenyl)amino) cinnamic acid, 3,4-(2,5-pyrrolidinedione) cinnamic acid, or a combination thereof.

4. The nanocrystal of claim 1 , wherein the first ligand is an alkyl carboxylate.

5. The nanocrystal of claim 1 ,

wherein the first ligand is oleate.

6. The nanocrystal of claim 1 , wherein the nanocrystal core has an average particle size between 1 nm and 100 nm.

7. The nanocrystal of claim 1 , wherein the mixed alloy comprises at least two of a Group II element, a Group III element, a Group IV element, a Group V element, Group VI element, a noble metal, or a combination thereof.

8. The nanocrystal of claim 7 , wherein the mixed alloy comprises at least one of PbS, PbSe, PbTe, CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, GaN, GaP, GaAs, InP, InAs, Si, Ge, Au, Ag, Pt, Cu, Ni, AgSbS 2 , AgSbSe 2 , CuInS 2 , CuInSez, CuInSSe, CuzSnS 3 , CuzSnSe 3 , CZTS, CZTSe, or CZTSSe, or a combination thereof.

9. The composition of claim 8 , wherein the mixed alloy core comprises at least one of PbS, PbSe, or a combination thereof.

10. The nanocrystal of claim 1 , wherein the second portion is between 10% and 90% of the surface.

11. The composition of claim 10 , wherein the second portion is between 30% and 70% of the surface.

12. A method comprising:

adding a molecule to a first solution comprising a first solvent and a starting nanocrystal, wherein:

the starting nanocrystal comprises a mixed alloy core and a starting ligand coordinated to a surface of the mixed alloy core,

the starting ligand comprises at least one of an alkyl carboxylate, an alkyl phosphonate, an alkyl thiolate, or a combination thereof,

the adding results in at least a portion of the molecule forming an exchange ligand that is different than the starting ligand,

the starting ligand and the exchange ligand have a ligand-ligand coupling energy less than 0.44 k B T, where k B is the Boltzmann constant and T is the temperature in Kelvin, and

the adding results in the forming of a nanocrystal comprising the mixed alloy core and a Janus ligand shell comprising the starting ligand coordinated to a first portion of the surface and the exchange ligand coordinated to a second portion of the surface.

13. The method of claim 12 , wherein the first solution is maintained at a temperature between 20° C. and 30° C.

14. The method of claim 12 , wherein the adding of the molecule results in a ratio of moles of exchange ligand to moles of mixed alloy core between 1:10 and 1000:1.

15. The method of claim 14 , wherein the ratio is between 1:1 and 100:1.

16. The method of claim 14 , wherein the exchange ligand comprises at least one of cinnamate, a functionalized cinnamate, or a combination thereof.

17. The method of claim 12 , further comprising, prior to the adding:

preparing the first solution comprising the mixed alloy core, the starting ligand, and the first solvent to produce the starting nanocrystal, wherein:

the first solvent has a high solubility for the mixed alloy core.

18. The method of claim 12 , wherein the first solvent comprises at least one of pentane, hexane, heptane, octane, cyclohexane, toluene, benzene, chlorobenzene, dichlorobenzene, nitrobenzene, dichloromethane, tetrachoroethylene, chloroform, carbon tetrachloride, acetone, acetonitrile, methyl acetate, ethyl acetate, tetrahydrofuran, diethyl ether, methanol, ethanol, propanol, butanol, N-methylformamide, N,N-dimethylformamide, dimethyl sulfoxide, water, or a combination thereof.

19. The method of claim 12 , wherein the starting ligand is an alkyl carboxylate.

20. The method of claim 19 , wherein the starting ligand is oleate.

Assignments (4)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 28, 2025
From: KROUPA, DANIEL, MR.
To: THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE
Reel/Frame 071854/0287 →
CONFIRMATORY LICENSE Recorded May 18, 2022
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 059941/0535 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 30, 2021
From: BEARD, MATTHEW CRAIG; HUANG, ZHIYUAN
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 058237/0668 →
Continuity (2)
Provisional Application 62861850 · Jun 14, 2019
Related Publication 20220259490A1 · Aug 18, 2022
References Cited (46)
US 10128390B2 · Santiago-Berrios · 2018 [cited by examiner]
US 20080234394A1 · Hong · 2008 [cited by examiner]
US 20150218442A1 · Jun et al. · 2015 [cited by applicant]
US 20150233936A1 · Tulsky et al. · 2015 [cited by applicant]
US 20170362255A1 · Beard et al. · 2017 [cited by applicant]
US 20190367805A1 · Kim et al. · 2019 [cited by applicant]
US 20200067006A1 · Ippen · 2020 [cited by examiner]
WO 2019084119A1 · 2019 [cited by applicant]
WO 20200067006A1 · 2020 [cited by applicant]
Babajani et al., J. Phys. Chem. C, 2014, 118, 27142-27149. Published online Oct. 27, 2014 (Year: 2014). [cited by examiner]
Bronstein et al., ACS Nano, 2019, 13, 38393846. Published online Mar. 11, 2019 (Year: 2019). [cited by examiner]
Vilain et al., J. Mater. Chem, 2007, 17, 3509-3514. published online Jun. 19, 2007 (Year: 2007). [cited by examiner]
Amin, V.A. et al., “Dependence of the Band Gap of CdSe Quantum Dots on the Surface Coverage and Binding Mode of an Exciton-Delocalizing Ligand, Methylthiophenolate,” Journal of Physical Chemistry C, vol. 119, 2015, 7 pa… [cited by applicant]
Bhattacharya, D. et al., “Designing Coupled Quantum Dots with ZnS-CdSe Hybrid Structures for Enhancing Exciton Lifetime,” Journal of Physical Chemistry C, vol. 122, 2018, 11 pages. [cited by applicant]
Coleman, B. et al., “Amphiphilic Quantum Dots with Asymmetric, Mixed Polymer Brush Layers: From Single Core-Shell Nanoparticles to Salt-Induced Vesicle Formation,” Polymers, vol. 10, No. 327, 2018, 14 pages. [cited by applicant]
Du, J. et al., “Anisotropic particles with patchy, multicompartment and Janus architectures: preparation and application,” Chem Soc. Rev., vol. 40, 2011, 15 pages. [cited by applicant]
Ebbens, S.J. et al., “Catalytic Janus Colloids: Controlling Trajectories of Chemical Microswimmers,” Accounts of Chemical Research, vol. 51, 2018, 9 pages. [cited by applicant]
Embden, J.V. et al., “The formation mechanism of Janus nanostructures in one-pot reactions: the case of Ag-Ag8GeS6,” Journal of Materials Chemistry A, vol. 4, 2016, 11 pages. [cited by applicant]
Falireas, P.G. et al., “pH-responsive polyampholytic hybrid Janus nanoparticles,” Elsevier Polymer, vol. 130, 2017, 11 pages. [cited by applicant]
Frederick, M.T. et al., “Relaxation of Exciton Confinement in CdSe Quantum Dots by Modification with a Conjugated Dithiocarbamate Ligand,” ACS Nano, vol. 4, No. 6, 2010, 6 pages. [cited by applicant]
Gandra, N. et al., “Bimetallic Janus nanostructures via programmed shell growth,” Nanoscale, vol. 5, 2013, 4 pages. [cited by applicant]
Giansante,C. et al., “Darker-than-Black” PbS Quantum Dots: Enhancing Optical Absorption of Colloidal Semiconductor Nanocrystals via Short Conjugated Ligands, Journal of the American Chemical Society, vol. 137, 2015, 12 … [cited by applicant]
Green, M.L.H., “A new approach to the formal classification of covalent compounds of the elements,” Journal of Organometallic Chemistry, vol. 500, 1995, 22 pages. [cited by applicant]
Harris, R.D. et al., “Role of Interligand Coupling in Determining the Interfacial Electronic Structure of Colloidal CdS Quantum Dots,” ACS Nano, vol. 10, 2016, 9 pages. [cited by applicant]
Harris, R.D. et al., “Electronic Processes within Quantum Dot-Molecule Complexes,” Chemical Reviews, vol. 116, 2016, 55 pages. [cited by applicant]
Hendricks, M.P. et al., “A tunable library of substituted thiourea precursors to metal sulfide nanocrystals,” Science, vol. 348, Issue 6240, 2015, 6 pages. [cited by applicant]
Jana, S. et al., “Ligand-induced twisting of nanoplatelets and their self-assembly into chiral ribbons,” Science Advances Research Article, vol. 3, 2017, 7 pages. [cited by applicant]
Jiang, Z. et al., “Subnanometre ligand-shell asymmetry leads to Janus-like nanoparticle membranes,” Nature Materials Letters, vol. 14, 2015, 7 pages. [cited by applicant]
Kroupa, D.M. et al., “In situ spectroscopic characterization of a solution-phase X-type ligand exchange at colloidal lead sulphide quantum dot surfaces,” ChemComm Communication, vol. 52, 2016, 4 pages. [cited by applicant]
Kroupa, D.M. et al., “Tuning colloidal quantum dot band edge positions through solution-phase surface chemistry modification,” Nature Communications, DOI: 10.1038/ncomms15257; 8 pages. [cited by applicant]
Kroupa, D.M. et al., “Optical Absorbance Enhancement in PbS QD/Cinnamate Ligand Complexes,” Journal of Physical Chemistry Letters, vol. 9, 2018, 9 pages. [cited by applicant]
Liu,X. et al., “Determination of monolayer-protected gold nanoparticle ligand-shell morphology using NMR,” Nature Communications, vol. 3, 2012, 9 pages. [cited by applicant]
Moreels, I. et al., “Ligand AdsorptionDesorption on Sterically Stabilizined InP Colloidal Nanocrystals: Observation and Thermodynamic Analysis,” ChemPhysChem, vol. 7, 2006, 4 pages. [cited by applicant]
Moreels, I. et al., “Size-Dependent Optical Properties of Colloidal PbS Quantum Dots,” ACS Nano, vol. 3, No. 10, 2009 8 pages. [cited by applicant]
Nomoev, A.V. et al, “Synthesis, Characterization, and Mechanism of Formation of Janus-Like Nanoparticles of Tantalum Silicide-Silicon (TaSix/Si),” Nanomaterials, vol. 5, 2015, 10 pages. [cited by applicant]
Ong, Q. et al., “Characterization of Ligand Shell for Mixed-Ligand Coated Gold Nanoparticles,” Accounts of Chemical Research, vol. 50, 2017, 9 pages. [cited by applicant]
Owen, J., “The coordination chemistry of nanocrystal surfaces,” Science, vol. 347, Issue 6222, 2015, 3 pages. [cited by applicant]
Percebom, A.M. et al., “Janus gold nanoparticles obtained via spontaneous binary polymer shell segregation,” ChemComm Communication, vol. 52, 2016, 4 pages. [cited by applicant]
Ruhland, T.M. et al., “Nanoscale hybrid silica/polymer Janus particles with a double-responsive hemicorona,” Polymer, vol. 79, 2015, 10 pages. [cited by applicant]
Schnitzenbaumer, K.J. et al., “Chalcogenide-Ligand Passivated CdTe Quantum Dots Can Be Treated as Core/Shell Semiconductor Nanostructures,” Journal of Physical Chemistry C, vol. 118, 2014, 9 pages. [cited by applicant]
Sologan, M. et al., “Patchy and Janus Nanoparticles by Self-Organization of Mixtures of Fluorinated and Hydrogenated Alkanethiolates on the Surface of a Gold Core,” ACS Nano, vol. 10, 2016, 10 pages. [cited by applicant]
Widmer-Cooper, A. et al., “Ligand-Mediated Interactions between Nanoscale Surfaces Depend Sensitively and Nonlinearly on Temperature, Facet Dimensions, and Ligand Coverage,” ACS Nano, Vo. 10, 2016, 11 pages. [cited by applicant]
Yuwen, L. et al., “One-Pot Encapsulation of Luminescent Quantum Dots Synthesized in Aqueous Solution by Amphiphillic Polymers,” Wiley Small, vol. 7, No. 10, 2011, 8 pages. [cited by applicant]
Zhang, J. et al., “Preparation of Cd/Pb Chalcogenide Heterostructured Janus Particles via Controllable Cation Exchange,” ACS Nano Vol. 9, No. 7, 2015, 13 pages. [cited by applicant]
Zhang, Z. et al., “Tethered Nano Building Blocks: Toward a Conceptual Framework for Nanoparticle Self-Assembly,” Nano Letters, vol. 3, No. 10, 2003, 6 pages. [cited by applicant]
Search Report and Written Opinion from Corresponding PCT Patent Application No. PCT/US20/37073, dated Sep. 11, 2020, 10 pages. [cited by applicant]