IP Library › Granted Patent US 12,625,134
Granted Patent B2
US 12,625,134 · App. 17/001,401 · Granted May 12, 2026

Complex liquid crystal droplets

Inventors: Timothy Manning Swager (Newton, MA); Cassandra Zentner (Brighton, MA); Alberto Concellon Allueva (Boston, MA)
Assignee: Massachusetts Institute of Technology
G01N33/5432B01F23/414C12Q1/6834G01N21/59G01N21/77G01N33/54366G01N2021/7783
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Quick Facts
Patent No.
US 12,625,134
App. No.
17/001,401
Granted
May 12, 2026
Kind
B2
Abstract

Articles (e.g., a colloid) and methods for providing complex colloids comprising a hydrocarbon phase (e.g., a hydrocarbon phase comprising a liquid crystal) and a fluorocarbon phase are generally described. In some embodiments, the hydrocarbon phase and the fluorocarbon phase are distinct.

Claims (35)

1 . An article, comprising:

an aqueous phase;

a mesogenic surfactant;

a droplet, wherein the droplet comprises a hydrocarbon phase, second phase immiscible with the hydrocarbon phase such that an interface is formed between the hydrocarbon phase and the second phase,

wherein the article comprises a second interface formed between the hydrocarbon phase and the aqueous phase, wherein the hydrocarbon phase comprises a liquid crystal, and

wherein the mesogenic surfactant anchors the liquid crystal to the second interface thereby directing orientation of the molecules of the liquid crystal within the droplet.

2 . The article of claim 1 , wherein the second phase comprises a fluorocarbon phase, and wherein the hydrocarbon phase and the second phase have a relative interfacial tension of at least 3 mN/m.

3 . The article of claim 1 , wherein the liquid crystal is smetically ordered.

4 . The article of claim 1 , wherein the liquid crystal is cholesterically ordered.

5 . The article of claim 1 , wherein the second phase is a fluorocarbon phase comprising a hydrofluoroether.

6 . The article of claim 1 , wherein the droplet comprises a Janus droplet.

7 . The article of claim 1 , wherein the droplet comprises a plurality of Janus droplets.

8 . The article of claim 1 , wherein the hydrocarbon phase and the second phase form a Janus droplet.

9 . The article of claim 1 , wherein the hydrocarbon phase and the second phase form an asymmetric Janus droplet.

10 . The article of claim 1 , wherein the mesogenic surfactant is a nonionic surfactant.

11 . The article of claim 1 , further comprising an emulsifying agent.

12 . The article of claim 1 , wherein the second phase comprises a fluorocarbon phase, and wherein the aqueous phase, the hydrocarbon phase, and/or the second phase have a relative interfacial tension of at least 4 mN/m and at most 8 mN/m.

13 . The article of claim 1 , wherein the liquid crystal comprises at least one point defect.

14 . The article of claim 1 , wherein the droplet further comprises a plurality of functional groups dispersed uniformly over a surface at a first temperature such that the plurality of functional groups localizes into one of more clusters by a phase transition of the liquid crystal within the droplet.

15 . The article of claim 1 , wherein molecules of the liquid crystal align perpendicularly to the aqueous phase.

16 . The article of claim 1 , wherein molecules of the liquid crystal align parallel to the aqueous phase.

17 . An article, comprising:

an aqueous phase;

a nonionic surfactant;

a droplet, wherein the droplet comprises a hydrocarbon phase, second phase immiscible with the hydrocarbon phase such that an interface is formed between the hydrocarbon phase and the second phase,

wherein the article comprises a second interface formed between the hydrocarbon phase and the aqueous phase, wherein the hydrocarbon phase comprises a liquid crystal, and

wherein the nonionic surfactant anchors the liquid crystal to the second interface thereby directing orientation of the molecules of the liquid crystal within the droplet, and wherein the nonionic surfactant comprises Formula (I):

wherein

 designates connection from an intervening chemical species.

18 . A method for preparing the article of claim 17 , comprising:

providing an aqueous phase, a hydrocarbon phase, and a fluorocarbon phase, wherein the hydrocarbon phase comprises a liquid crystal; providing a non-ionic surfactant, wherein the nonionic surfactant comprises Formula (I):

wherein,

 designates connection from an intervening chemical species; emulsifying the aqueous phase, the hydrocarbon phase, the fluorocarbon phase with an emulsifying agent; and evaporating the emulsifying agent to prepare a colloid.

19 . The method of claim 18 , comprising applying a stimulus to change the position of the hydrocarbon phase and the fluorocarbon phase.

20 . The article of claim 19 , wherein the stimulus is light.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2021
From: SWAGER, TIMOTHY MANNING; ZENTNER, CASSANDRA; CONCELLON ALLUEVA, ALBERTO
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 055716/0073 →
Continuity (7)
Continuation In Part 16201961 · Nov 27, 2018
Continuation In Part 16113520 · Aug 27, 2018
Continuation 15269543 · Sep 19, 2016
Continuation In Part 14929117 · Oct 30, 2015
Provisional Application 62925756 · Oct 24, 2019
Provisional Application 62073896 · Oct 31, 2014
Related Publication 20210041425A1 · Feb 11, 2021
References Cited (224)
US 3826613A · Parikh et al. · 1974 [cited by applicant]
US 4663277A · Wang · 1987 [cited by applicant]
US 4870026A · Wands et al. · 1989 [cited by applicant]
US 4912034A · Kalra et al. · 1990 [cited by applicant]
US 5066465A · Kano et al. · 1991 [cited by applicant]
US 5217648A · Beissinger et al. · 1993 [cited by applicant]
US 5332661A · Adamczyk et al. · 1994 [cited by applicant]
US 5387676A · Zavada et al. · 1995 [cited by applicant]
US 5516635A · Ekins et al. · 1996 [cited by applicant]
US 5980936A · Krafft et al. · 1999 [cited by applicant]
US 6180418B1 · Lee · 2001 [cited by applicant]
US 6271202B1 · Kudsk · 2001 [cited by applicant]
US 6710092B2 · Scher et al. · 2004 [cited by applicant]
US 7067590B2 · Sato et al. · 2006 [cited by applicant]
US 7625951B2 · Daunert et al. · 2009 [cited by applicant]
US 7767017B2 · Lahann et al. · 2010 [cited by applicant]
US 7947772B2 · Lahann et al. · 2011 [cited by applicant]
US 8241651B2 · Lahann · 2012 [cited by applicant]
US 9415392B2 · Ismagilov et al. · 2016 [cited by applicant]
US 10005058B2 · Swager et al. · 2018 [cited by applicant]
US 10060913B2 · Swager · 2018 [cited by examiner]
US 10252231B2 · Swager et al. · 2019 [cited by applicant]
US 11119098B2 · Swager · 2021 [cited by examiner]
US 11229892B2 · Swager · 2022 [cited by examiner]
US 20020040065A1 · Scher et al. · 2002 [cited by applicant]
US 20020090608A1 · Palese et al. · 2002 [cited by applicant]
US 20040069857A1 · Leblans et al. · 2004 [cited by applicant]
US 20040176479A1 · Scher et al. · 2004 [cited by applicant]
US 20050145829A1 · Leyrer · 2005 [cited by examiner]
US 20060154234A1 · Winther et al. · 2006 [cited by applicant]
US 20060201390A1 · Lahann et al. · 2006 [cited by applicant]
US 20070105972A1 · Doyle et al. · 2007 [cited by applicant]
US 20070237800A1 · Lahann et al. · 2007 [cited by applicant]
US 20080234394A1 · Hong et al. · 2008 [cited by applicant]
US 20080242774A1 · Lahann et al. · 2008 [cited by applicant]
US 20090232856A1 · Patel · 2009 [cited by applicant]
US 20090306311A1 · Reed · 2009 [cited by applicant]
US 20100062525A1 · Abbott et al. · 2010 [cited by applicant]
US 20100069726A1 · Levinson · 2010 [cited by applicant]
US 20100097687A1 · Lipovetskaya et al. · 2010 [cited by applicant]
US 20100099048A1 · Thomas et al. · 2010 [cited by applicant]
US 20110003401A1 · Oscarsson et al. · 2011 [cited by applicant]
US 20110104777A1 · Marquez et al. · 2011 [cited by applicant]
US 20110195394A1 · Selinfreund et al. · 2011 [cited by applicant]
US 20110195421A1 · Selinfreund et al. · 2011 [cited by applicant]
US 20110196085A1 · Selinfreund et al. · 2011 [cited by applicant]
US 20110223590A1 · Chiou et al. · 2011 [cited by applicant]
US 20120028342A1 · Ismagilov et al. · 2012 [cited by applicant]
US 20120045748A1 · Willson et al. · 2012 [cited by applicant]
US 20120248020A1 · Granick et al. · 2012 [cited by applicant]
US 20120288852A1 · Willson et al. · 2012 [cited by applicant]
US 20120319043A1 · Stepien et al. · 2012 [cited by applicant]
US 20120328654A1 · Huang et al. · 2012 [cited by applicant]
US 20140016177A1 · Aizenberg et al. · 2014 [cited by applicant]
US 20140227684A1 · Hindson et al. · 2014 [cited by applicant]
US 20140323330A1 · Bergo · 2014 [cited by applicant]
US 20140350168A1 · Bormashenko · 2014 [cited by applicant]
US 20150238636A1 · Homyk et al. · 2015 [cited by applicant]
US 20160114325A1 · Tang et al. · 2016 [cited by applicant]
US 20160151753A1 · Swager et al. · 2016 [cited by applicant]
US 20160151756A1 · Swager et al. · 2016 [cited by applicant]
US 20160193602A1 · Tsai et al. · 2016 [cited by applicant]
US 20160235670A1 · Mason et al. · 2016 [cited by applicant]
US 20170368865A1 · Macpherson et al. · 2017 [cited by applicant]
US 20170371151A1 · Brassard et al. · 2017 [cited by applicant]
US 20180080927A1 · Swager · 2018 [cited by examiner]
US 20190170736A1 · Swager · 2019 [cited by examiner]
US 20190170737A1 · Swager et al. · 2019 [cited by applicant]
US 20190184356A1 · Swager et al. · 2019 [cited by applicant]
US 20190212333A1 · Swager et al. · 2019 [cited by applicant]
US 20200056996A1 · Zarzar · 2020 [cited by examiner]
US 20200166503A1 · Swager et al. · 2020 [cited by applicant]
US 20210080456A1 · Swager et al. · 2021 [cited by applicant]
US 20220205989A1 · Swager et al. · 2022 [cited by applicant]
EP 135352A · 1985 [cited by applicant]
EP 161328A · 1985 [cited by applicant]
EP 323909A · 1989 [cited by applicant]
EP 1365240A2 · 2003 [cited by applicant]
JP H0599926A · 1993 [cited by applicant]
JP 2013518167A · 2013 [cited by applicant]
WO WO9214154A1 · 1992 [cited by applicant]
WO WO199217179A1 · 1992 [cited by applicant]
WO WO199531500A2 · 1995 [cited by applicant]
WO WO2004063707A2 · 2004 [cited by applicant]
WO WO2008066463A1 · 2008 [cited by applicant]
WO WO2009061372A1 · 2009 [cited by applicant]
WO WO2009101113A2 · 2009 [cited by applicant]
WO WO2009151390A1 · 2009 [cited by applicant]
WO WO2010092333A1 · 2010 [cited by applicant]
WO WO2011093733A1 · 2011 [cited by applicant]
WO 2013059294A1 · 2013 [cited by applicant]
WO WO2015051179A1 · 2015 [cited by applicant]
WO 2016103226A2 · 2016 [cited by applicant]
Wang et al. Thermally reconfigurable Janus droplets with nematic liquid crystalline and isotropic perfluorocarbon oil compartments. Soft Matter, 2019, 15, 2580-2590. Published online Feb. 27, 2019. (Year: 2019). [cited by examiner]
Definition of singularity. https://www.dictionary.com/browse/singularity. As viewed on May 29, 2024. (Year: 2024). [cited by examiner]
U.S. Appl. No. 16/284,722, filed Feb. 25, 2019, Swager et al. [cited by applicant]
U.S. Appl. No. 16/113,520, filed Aug. 27, 2018, Swager et al. [cited by applicant]
U.S. Appl. No. 17/545,979, filed Dec. 8, 2021, Swager et al. [cited by applicant]
International Search Report and Written Opinion mailed Jan. 22, 2016 for Application No. PCT/US2015/058268. [cited by applicant]
International Preliminary Report on Patentability mailed May 11, 2017 for Application No. PCT/US2015/058268. [cited by applicant]
Extended European Search Report mailed Jun. 11, 2018 for Application No. EP 15855674.6. [cited by applicant]
International Search Report and Written Opinion mailed Jan. 22, 2016 for Application No. PCT/US2015/058286. [cited by applicant]
International Preliminary Report on Patentability mailed May 11, 2017 for Application No. PCT/US2015/058286. [cited by applicant]
International Search Report and Written Opinion mailed Nov. 30, 2017 for Application No. PCT/US2017/052209. [cited by applicant]
International Preliminary Report on Patentability mailed Mar. 28, 2019 for Application No. PCT/US2017/052209. [cited by applicant]
[No Author Listed], Definition of Associate. Retrieved from https://www.vocabulary.com/associate. Accessed on Apr. 22, 2020. 4 pages. [cited by applicant]
Alino et al., Liquid crystal droplets as a hosting and sensing platform for developing immunoassays. Langmuir. Aug. 2011;27:11784-9. [cited by applicant]
Augustin et al., Nano- and micro-structured assemblies for encapsulation of food ingredients. Chem Soc Rev. Apr. 2009;38(4):902-12. doi: 10.1039/b801739p. Epub Dec. 4, 2008. [cited by applicant]
Bedford et al., Solubilities and vol. Changes Attending Mixing for the System: Perfluoro- n-hexane-n-Hexane. J. Am. Chem. Soc., 1958, 80(2):282-285. [cited by applicant]
Berger et al., Stimuli-responsive bicomponent polymer Janus particles by “grafting from”/“grafting to” approaches. Macromolecules. 2008;41:9669-76. Epub Nov. 21, 2008. [cited by applicant]
Besnard et al., Multiple emulsions controlled by stimuli-responsive polymers. Adv Mater. May 28, 2013;25(20):2844-8. doi: 10.1002/adma.201204496. Epub Mar. 11, 2013. [cited by applicant]
Brown et al., Stimuli-responsive surfactants. Soft Matter 2013; 9:2365-2374. [cited by applicant]
Chakravarti et al., Liquid membrane multiple emulsion process of chromium(VI) separation from waste waters. Colloid Surface A 1995; 103:59-71. [cited by applicant]
Chen et al., Janus particles templated from double emulsion droplets generated using microfluidics. Langmuir. 2009;25(8):4320-3. Epub Mar. 18, 2009. [cited by applicant]
Chen et al., Photoresponsive Monodisperse Cholesteric Liquid Crystalline Microshells for Tunable Omnidirectional Lasing Enabled by a Visible Light-Driven Chiral Molecular Switch. Adv Op Mat 2014; 2(9): 845-8. [cited by applicant]
Chevallier et al., Photofoams: remote control of foam destabilization by exposure to light using an azobenzene surfactant. Langmuir. Feb. 7, 2012;28(5):2308-12. doi: 10.1021/la204200z. Epub Jan. 27, 2012. [cited by applicant]
Choi et al., Microfluidic Design of Complex Emulsions. ChemPhysChem 2014; 15: 21-290. [cited by applicant]
Choi et al., One step formation of controllable complex emulsions: from functional particles to simultaneous encapsulation of hydrophilic and hydrophobic agents into desired position. Adv mater. 2013; 6 pages. [cited by applicant]
Choi et al., Patterned fluorescent particles as nanoprobes for the investigation of molecular interactions. Nano Letters. 2003;3(8):995-1000. Epub Jul. 11, 2003. [cited by applicant]
De La Fuente et al., Exploring the efficiency of gallic acid-based dendrimers and their block copolymers with PEG as gene carriers. Nanomed. 2012;7(11):1667-81. Epub Jul. 20, 2012. [cited by applicant]
Dominguez et al., Modelling and understanding of the vapour-liquid and liquid-liquid interfacial properties for the binary mixture of n-heptane and perfluoro-n-hexane. J. Mol. Liq. 2013; 185:36-43. [cited by applicant]
Engel et al., Insulin: intestinal absorption as water-in-oil-in-water emulsions. Nature. Aug. 24, 1968;219(5156):856-7. [cited by applicant]
Gao et al., Double Emulsion Templated Microcapsules with Single Hollow Cavities and Thickness-Controllable Shells. Langmuir, 2009, 25(6): 3832-3838. [cited by applicant]
Ge et al., Droplet topology control of Janus emulsion prepared in one-step high energy mixing. Soft Matter. 2014;10:4498-505. Epub Apr. 8, 2014. [cited by applicant]
Gladysz et al., Structural, physical, and chemical properties of fluorous compounds. Top Curr Chem. 2012;308:1-23. doi: 10.1007/128_2011_282. [cited by applicant]
Gresham et al., Use of a sustained-release multiple emulsion to extend the period of radio protection conferred by cysteamine. Nature. Nov. 19, 1971;234(5325):149-50. [cited by applicant]
Guzowski et al., The structure and stability of multiple micro-droplets. Soft Matter 2012; 8: 7269-7278. [cited by applicant]
Haase et al., Tailoring of high-order multiple emulsions by the liquid-liquid phase separation of ternary mixtures. Angew Chem Int Ed. 2014;53:1-6. [cited by applicant]
Han et al., Retroreflective Janus microparticle as a nonspectroscopic optical immunosensing probe. ACS Appl Mater & Interfaces. May 4, 2016;8(17):10767-74. [cited by applicant]
Kaufmann et al., “Sandwich” microcontact printing as a mild route towards monodisperse Janus particles with tailored bifunctionality. Adv Mater. 2011;23:79-83; Supporting Information pp. 1-8. [cited by applicant]
Kaufmann et al., Bifunctional Janus beads made by “sandwich” microcontact printing using click chemistry. J Mater Chem. 2012;22:6190-9. Epub Feb. 17, 2012. Electronic suppl info pp. 1-9. [cited by applicant]
Kim et al., Fabrication of monodisperse gel shells and functional microgels in microfluidic devices. Angew Chem Int Ed Engl. 2007;46(11):1819-22. [cited by applicant]
Kumar et al., Multiple emulsions: a review. Int J Rec Adv Pharm Rsch. Jan. 2012; 2(1):9-19. [cited by applicant]
Lemal, Perspective on fluorocarbon chemistry. J Org Chem. Jan. 9, 2004;69(1):1-11. [cited by applicant]
Li et al., Synthesis of biofunctional Janus particles. Macromol Rapid Comm. 2015;36:1200-4. [cited by applicant]
Lone et al., Fabrication of polymeric Janus particles by droplet microfluidics. RSC Adv. 2014 4: 13322-13333. [cited by applicant]
McClain et al., Interfacial roughness in a near-critical binary fluid mixture: X-ray reflectivity and near-specular diffuse scattering. Eur. Phys. J. B. 1999; 10: 45-52. [cited by applicant]
McClements et al., Factors that affect the rate of oil exchange between oil-in-water emulsion droplets stabilized by a nonionic surfactant: Droplet size, surfactant concentration, and ionic strength. J. Phys. Chem. Jun.… [cited by applicant]
Mukerjee et al., Adsorption of fluorocarbon and hydrocarbon surfactants to air-water, hexane-water and perfluorohexane-water interfaces. Relative affinities and fluorocarbon-hydrocarbon nonideality effects. J. Phys. Che… [cited by applicant]
Nie et al., Janus and ternary particles generated by microfluidic synthesis: design, synthesis, and self-assembly. J Am Chem Soc. Jul. 26, 2006;128(29):9408-12. [cited by applicant]
Nisisako et al., Synthesis of monodisperse bicolored Janus particles with electrical anisotropy using a microfluidic co-flow system. Adv Mater. 2006;18:1152-6. [cited by applicant]
Niu et al., Optical biosensor based on liquid crystal droplets for detection of cholic acid. Optics Commun. 2016;381:286-91. [cited by applicant]
Patravale et al., Novel cosmetic delivery systems: an application update. Int J Cosmet Sci. Feb. 2008;30(1):19-33. doi: 10.1111/j.1468-2494.2008.00416.x. [cited by applicant]
Perro et al., Design and synthesis of Janus micro- and nanoparticles. J Mater Chem. 2005; 15:3745-60. Epub Jul. 25, 2005. [cited by applicant]
Riess, Overview of progress in the fluorocarbon approach to in vivo oxygen delivery. Biomater Artif Cells Immobilization Biotechnol. 1992;20(2-4):183-202. [cited by applicant]
Roh et al., Biphasic Janus particles with nanoscale anisotropy. Nat Mater. Oct. 2005;4:759-63. Epub Sep. 25, 2005. [cited by applicant]
Schutt et al., Injectable microbubbles as contrast agents for diagnostic ultrasound imaging: the key role of perfluorochemicals. Angew Chem Int Ed Engl. Jul. 21, 2003;42(28):3218-35. [cited by applicant]
Shah et al., Designer emulsions using microfluidics. Materials Today, 2011; 11: 18-27. [cited by applicant]
Shah et al., Janus Supraparticles by Induced Phase Separation of Nanoparticles in Droplets. Adv. Mater. 2009; 21: 1949-1953. doi: 10.1002/adma.200803115. [cited by applicant]
Shum et al., Droplet microfluidics for fabrication of non-spherical particles. Macromol Rapid Commun. Jan. 18, 2010;31(2):108-18. doi: 10.1002/marc.200900590. Epub Nov. 24, 2009. [cited by applicant]
Song et al., Monodisperse w/w/w/ double emulsion induced by phase separation. Langmuir. 2012;28:12054-12059. [cited by applicant]
Tanaka et al., Dual stimuli-responsive “mushroom-like” Janus polymer particles as particulate surfactants. Langmuir. Jul. 20, 2010;26(14):11732-6. doi: 10.1021/la101237c. [cited by applicant]
Tu et al., One-step encapsulation and triggered release based on Janus particle-stabilized multiple emulsions. Chem Commun (Camb). Dec. 21, 2014;50(98):15549-52. doi: 10.1039/c4cc07854c. Epub Oct. 30, 2014. [cited by applicant]
Utada et al., Monodisperse double emulsions generated from a microcapillary device. Science. Apr. 22, 2005;308(5721):537-41. [cited by applicant]
Walther et al., Janus particles. Soft Matter. 2008;4:663-8. Epub Feb. 26, 2008. [cited by applicant]
Wong et al., Bioinspired self-repairing slippery surfaces with pressure-stable omniphobicity. Nature. Sep. 21, 2011;477(7365):443-7. doi: 10.1038/nature10447. [cited by applicant]
Wu et al., Bioinspired nanocorals with decoupled cellular targeting and sensing functionality. Small. 2010;6(4):503-7. [cited by applicant]
Yusa et al., Fluorescence Studies of pH-Responsive Unimolecular Micelles Formed from Amphiphilic Polysulfonates Possessing Long-Chain Alkyl Carboxyl Pendants. Macromolecules. 2002; 35(27): 10182-88. doi: 10.1021/ma02129… [cited by applicant]
Zhang et al., Interfacial bioconjugation on emulsion droplet for biosensors. Bioorg Med Chem. Oct. 15, 2018;26(19):5307-13. Author manuscript. 20 pages. [cited by applicant]
Zhang et al., Janus emulsions for the detection of bacteria. ACS Central Sci. Apr. 26, 2017;3(4):309-13. [cited by applicant]
Zhao et al., Microfluidic mass-transfer control for the simple formation of complex multiple emulsions. Angew Chem Int Ed. 2009;48:7208-11. [cited by applicant]
[No Author Listed], Definition of Fluidic. Retrieved from https://www.merriam-webster.com/dictionary/fluidic. Last accessed on Apr. 14, 2021. 10 pages. [cited by applicant]
Axenov et al., Thermotropic Ionic Liquid Crystals. Materials. 2011;4:206-59. Epub Jan. 14, 2011. [cited by applicant]
Belmonte et al., Patterned Full-Color Reflective Coatings Based on Photonic Cholesteric Liquid-Crystalline Particles. ACS Appl Mater Interfaces. Apr. 17, 2019;11(15):14376-14382. doi: 10.1021/acsami.9b02680. Epub Apr. 8… [cited by applicant]
Bijlard et al., Functional Colloidal Stabilization. Advanced Materials Interfaces. Jan. 2019;4(1):1600443. Epub Nov. 8, 2016. 31 pages. [cited by applicant]
Brake et al., Biomolecular interactions at phospholipid-decorated surfaces of liquid crystals. Science. Dec. 19, 2003;302(5653):2094-7. doi: 10.1126/science.1091749. [cited by applicant]
Braun et al., Functional liquid crystalline particles and beyond. Liquid Crystals. 2019;46(13-14):2023-41. [cited by applicant]
Broer et al., Functional organic materials based on polymerized liquid-crystal monomers: supramolecular hydrogen-bonded systems. Angew Chem Int Ed Engl. Jul. 16, 2012;51(29):7102-9. doi: 10.1002/anie.201200883. Epub May… [cited by applicant]
Brunsveld et al., Hierarchical Growth of Chiral Self-Assembled Structures in Protic Media. J. Am. Chem. Soc. 2000;122(26):6175-82. Epub Jun. 17, 2000. [cited by applicant]
Cipparrone et al., Chiral self-assembled solid microspheres: a novel multifunctional microphotonic device. Adv Mater. Dec. 22, 2011;23(48):5773-8. doi: 10.1002/adma.201102828. Epub Nov. 15, 2011. [cited by applicant]
Concellón et al., Dynamic Complex Liquid Crystal Emulsions. J. Am. Chem. Soc. 2019;141(45):18246-55. Epub Nov. 1, 2019. [cited by applicant]
Craig et al., Effect of Spacer Length on the Thermal Properties of Side-Chain Liquid Crystal Polymethacrylates. 2. Synthesis and Characterization of the Poly[.omega.-(4′-cyanobiphenyl-4-yloxy)alkyl methacrylate]s. Macro… [cited by applicant]
Eremin et al., Azodendrimers as a photoactive interface for liquid crystals. Liquid Crystals. 2018;45(13-15):2121-31. Epub Aug. 17, 2018. [cited by applicant]
Fleischmann et al., One-piece micropumps from liquid crystalline core-shell particles. Nat Commun. 2012;3:1178. doi: 10.1038/ncomms2193. Epub Nov. 6, 2012. 8 pages. [cited by applicant]
Forth et al., Building Reconfigurable Devices Using Complex Liquid-Fluid Interfaces. Advanced Materials. May 2019;31(18):1806370. Epub Mar. 4, 2019. 39 pages. [cited by applicant]
Ge et al., Recent studies of Janus emulsions prepared by one-step vibrational mixing. Current Opinion in Colloid & Interface Science. Oct. 2016;25:58-66. [cited by applicant]
He et al., Interfacial Polymerization on Dynamic Complex Colloids: Creating Stabilized Janus Droplets. ACS Applied Materials & Interfaces. 2017;9(8):7804-11. Epub Feb. 15, 2017. [cited by applicant]
Heinze et al., Microfluidic immunosensor for rapid and sensitive detection of bovine viral diarrhea virus. Sensors and Actuators B. 2009;138:491-6. [cited by applicant]
Hessberger et al., Interfacial Self-Assembly of Amphiphilic Dual Temperature Responsive Actuating Janus Particles. Adv Funct Mater. 2018;28(21):1800629. 10 pages. [cited by applicant]
Jampani et al., Micrometer-Scale Porous Buckling Shell Actuators Based on Liquid Crystal Networks. Advanced Functional Materials. 2018;28(31):1801209. Epub Jun. 5, 2018. 9 pages. [cited by applicant]
Jeong et al., Liquid crystal Janus emulsion droplets: preparation, tumbling, and swimming. Soft Matter. Sep. 14, 2015;11(34):6747-54. doi: 10.1039/c5sm01053e. Epub Jul. 14, 2015. [cited by applicant]
Joyce, Fluidics—Basic Components and Applications. U.S. Army Electronics Research and Development Command. Harry Diamond Laboratories. Adelphi, MD. Aug. 1983. 24 pages. [cited by applicant]
Kang et al., Amplified Photon Upconversion by Photonic Shell of Cholesteric Liquid Crystals. J Am Chem Soc. Apr. 26, 2017;139(16):5708-5711. doi: 10.1021/jacs.7b01981. Epub Apr. 17, 2017. [cited by applicant]
Kato et al., Functional Liquid Crystals towards the Next Generation of Materials. Angew Chem Int Ed Engl. Apr. 9, 2018;57(16):4355-4371. doi: 10.1002/anie.201711163. Epub Mar. 13, 2018. [cited by applicant]
Lin et al., Endotoxin-Induced Structural Transformations in Liquid Crystalline Droplets. Science. Jun. 10, 2011; 332(6035): 1297-1300. Epub May 11, 2011. Author manuscript provided. 8 pages. [cited by applicant]
Lin et al., Morphology-Dependent Luminescence in Complex Liquid Colloids. J Am Chem Soc. Mar. 6, 2019;141(9):3802-3806. doi: 10.1021/jacs.8b13215. Epub Feb. 20, 2019. Author manuscript provided. 16 pages. [cited by applicant]
McClements et al., Structured emulsion-based delivery systems: controlling the digestion and release of lipophilic food components. Adv Colloid Interface Sci. Sep. 15, 2010;159(2):213- 28. doi: 10.1016/j.cis.2010.06.010… [cited by applicant]
Miller et al., Design of Functional Materials based on Liquid Crystalline Droplets. Chem Mater. Jan. 14, 2014;26(1):496-506. doi: 10.1021/cm4025028. Author manuscript provided. 26 pages. [cited by applicant]
Miniewicz et al., Photochromic and nonlinear optical properties of azo-functionalized POSS nanoparticles dispersed in nematic liquid crystals. Journal of Materials C. 2014;2:432-40. Epub Oct. 30, 2013. [cited by applicant]
Mondiot et al., Liquid crystal-based emulsions for synthesis of spherical and non-spherical particles with chemical patches. J Am Chem Soc. Jul. 10, 2013;135(27):9972-5. doi: 10.1021/ja4022182. Epub Apr. 19, 2013. Autho… [cited by applicant]
Nagelberg et al., Reconfigurable and responsive droplet-based compound micro-lenses. Nat Commun. Mar. 7, 2017;8:14673. doi: 10.1038/ncomms14673. Epub Mar. 7, 2017. 9 pages. [cited by applicant]
Ohm et al., A continuous flow synthesis of micrometer-sized actuators from liquid crystalline elastomers. Adv Mater. Dec. 18, 2009;21(47):4859-62. doi: 10.1002/adma.200901522. [cited by applicant]
Schwartz et al., Cholesteric Liquid Crystal Shells as Enabling Material for Information-Rich Design and Architecture. Adv Mater. Jul. 2018;30(30):e1707382. doi: 10.1002/adma.201707382. Epub May 14, 2018. 19 pages. [cited by applicant]
Sivakumar et al., Liquid Crystal Emulsions as the Basis of Biological Sensors for the Optical Detection of Bacteria and Viruses. Advanced Functional Materials. 2009;19(14):2260-5. Epub Jul. 16, 2009. [cited by applicant]
Skarabot et al., Hierarchical self-assembly of nematic colloidal superstructures. Phys Rev E. Jun. 2008;77(6 Pt 1):061706. doi: 10.1103/PhysRevE.77.061706. Epub Jun. 12, 2008. 4 pages. [cited by applicant]
Tschierske, Development of structural complexity by liquid-crystal self-assembly. Angew Chem Int Ed Engl. Aug. 19, 2013;52(34):8828-78. doi: 10.1002/anie.201300872. Epub Aug. 9, 2013. [cited by applicant]
Van Der Asdonk et al., Liquid crystal templating as an approach to spatially and temporally organise soft matter. Chem Soc Rev. Oct. 2, 2017;46(19):5935-5949. doi: 10.1039/c7cs00029d. [cited by applicant]
Wang et al., Liquid crystals: emerging materials for use in real-time detection applications. Journal of Materials Chemistry C. 2015;3:9038-47. Epub Aug. 4, 2015. Author manuscript provided. 23 pages. [cited by applicant]
Wang et al., Thermally reconfigurable Janus droplets with nematic liquid crystalline and isotropic perfluorocarbon oil compartments. Soft Matter. Mar. 20, 2019;15(12):2580-2590. doi: 10.1039/c8sm02600a. Author manuscrip… [cited by applicant]
Wang et al., Topological defects in liquid crystals as templates for molecular self-assembly. Nat Mater. Jan. 2016;15(1):106-12. doi: 10.1038/nmat4421. Epub Sep. 21, 2015. [cited by applicant]
Yang et al., Microfluidic synthesis of multifunctional Janus particles for biomedical applications. Lab Chip. Jun. 2, 20121;12(12):2097-102. doi: 10.1039/c2lc90046g. Epub May 14, 2012. Author manuscript provided. 14 pag… [cited by applicant]
Yi et al., Janus particles for biological imaging and sensing. Analyst. Jun. 21, 2016;141(12):3526-39. doi: 10.1039/c6an00325g. Epub Apr. 7, 2016. Author manuscript provided. 24 pages. [cited by applicant]
Yoshida et al., Structurally Controlled Bio-hybrid Materials Based on Unidirectional Association of Anisotropic Microparticles with Human Endothelial Cells. Adv Mater. Dec. 2009;21:4920-5. [cited by applicant]
Yuet et al., Multifunctional Superparamagnetic Janus Particles. Langmuir. Mar. 16, 2010;26(6):4281-7. doi: 10.1021/1a903348s. Epub Oct. 20, 2009. [cited by applicant]
Zarzar et al., Dynamically reconfigurable complex emulsions via tunable interfacial tensions. Nature. Feb. 26, 2015;518(7540):520-4. doi: 10.1038/nature14168. Author manuscript provided. 20 pages. [cited by applicant]
Zeininger et al., Rapid Detection of Salmonella enterica via Directional Emission from Carbohydrate-Functionalized Dynamic Double Emulsions. ACS Cent Sci. May 22, 2019; 5(5):789-795. Epub Apr. 23, 2019. [cited by applicant]
Zeininger et al., Waveguide-based chemo- and biosensors: complex emulsions for the detection of caffeine and proteins. Lab on a Chip. 2019;19:1327-31. Epub Mar. 21, 2019. [cited by applicant]
Zhang et al., Emulsion Agglutination Assay for the Detection of Protein-Protein Interactions: An Optical Sensor for Zika Virus. ACS Sens. Jan. 25, 2019;4(1):180-184. doi: 10.1021/acssensors.8b01202. Epub Jan. 9, 2019. A… [cited by applicant]
Zhang et al., Fabrication of Janus droplets by evaporation driven liquid-liquid phase separation. Chemical Communications. 2016;52:5015-8. Epub Mar. 7, 2016. [cited by applicant]
Zhang et al., Janus Particle Synthesis, Assembly, and Application. Langmuir. 2017;33(28):6964-77. Epub Jul. 5, 2017. [cited by applicant]
Zhang et al., Toward Design Rules of Directional Janus Colloidal Assembly. Ann Rev Phys Chem. 2015;66:581-600. doi: 10.1146/annurev-physchem-040214-121241. Epub Feb. 4, 2015. [cited by applicant]
Zhang et al., Ultra-small droplet generation via volatile component evaporation. Lab Chip. Apr. 21, 2014;14(8):1395-400. doi: 10.1039/c31c51183a. [cited by applicant]
Anker et al., Magnetically modulated optical nanoprobes. Appl Phys Lett. 2003. 82(7): 1102-4. [cited by applicant]
Claessens et al., Highly Efficient Synthesis of Chloro- and Phenoxy-Substituted Subphthalocyanines. Jun. 26, 2003;2003(14):2547-51. [cited by applicant]
Erb et al., Towards holonomic control of Janus particles in optomagnetic traps. Adv Mater. Dec. 18, 2009;21(47):4825-9. [cited by applicant]
McNaughton et al., Compact sensor for measuring nonlinear rotational dynamics of driven magnetic microspheres with biomedical applications. J Magnet Magnet Materials. 2009; 321: 1648-52. [cited by applicant]
McNaughton et al., Single bacterial cell detection with nonlinear rotational frequency shifts of driven magnetic microspheres. Appl Phys Lett. 2007. 91: 224105. [cited by applicant]
Ong et al., Dynamic self-correcting nucleophilic aromatic substitution. Nat Chem. Sep. 3, 2018;10:1023-30. [cited by applicant]
Sun et al., Controlled production of size-tunable Janus droplets for submicron particle synthesis using an electrospray microfluidic chip. RSC Adv. 2016; 6: 12042-7. [cited by applicant]
Wang et al., Janus magneto-electric nanosphere dimers exhibiting unidirectional visible light scattering and strong electromagnetic field enhancement. ACS Nano. Jan. 27, 2015;9(1):436-48. doi: 10.1021/nn505606x. Epub Ja… [cited by applicant]
Yin et al., Versatile bifunctional magnetic-fluorescent responsive Janus supraballs towards the flexible bead display. Adv Mater. Jul. 12, 2011;23(26):2915-9. doi: 10.1002/adma.201100203. Epub Apr. 26, 2011. [cited by applicant]
Yu et al., Simultaneous detection of pathogenic bacteria using agglutination test based on colored silica nanoparticles. Curr Pharm Biotechnol. 2015;16(8):716-23. [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2020/042599 dated Dec. 3, 2020. [cited by applicant]
International Preliminary Report on Patentability (Chapter 1) for International Application No. PCT/US2020/042599 dated Mar. 31, 2022. [cited by applicant]