Photochromic Spatiotemporal Control of Bubble-Propelled Micromotors by a Spiropyran Molecular Switch

ACS Nano

Volumn 10, Issue 3, 2016, Pages 3543-3552

  Moo, James Guo Sheng ^a   Presolski, Stanislav ^a,b   Pumera, Martin ^a  

^a Nanyang Technological University   (Singapore)

^b YALE NUS COLLEGE   (Singapore)

Author keywords

control; micromotors; photochromic; self propulsion; spiropyrans

Indexed keywords

CONTROL; IRRADIATION; MICROMOTORS; STOCHASTIC SYSTEMS;

ATTRACTIVE STRATEGIES; CONTROLLED MOTIONS; IRRADIATION SOURCES; MOLECULAR SWITCHES; PHOTOCHROMIC; SELF PROPULSION; SPATIOTEMPORAL CONTROL; SPIROPYRANS;

PHOTOCHROMISM;

EID: 84961926679     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/acsnano.5b07847     Document Type: Article

References (82)

1. Wang, J. Nanomachines: Fundamentals and Applications; John Wiley & Sons: Weinheim, Germany, 2013, ISBN 978-3-527-33120-8.
2. Gao, W.; Wang, J. Synthetic Micro/Nanomotors in Drug Delivery Nanoscale 2014, 6, 10486-10494 10.1039/C4NR03124E
3. Gao, W.; Wang, J. The Environmental Impact of Micro/Nanomachines: A Review ACS Nano 2014, 8, 3170-3180 10.1021/nn500077a
4. Soler, L.; Sanchez, S. Catalytic Nanomotors for Environmental Monitoring and Water Remediation Nanoscale 2014, 6, 7175-7182 10.1039/c4nr01321b
5. Moo, J. G. S.; Pumera, M. Chemical Energy Powered Nano/Micro/Macromotors and the Environment Chem.-Eur. J. 2015, 21, 58-72 10.1002/chem.201405011
6. Zhao, G.; Wang, H.; Sanchez, S.; Schmidt, O. G.; Pumera, M. Artificial Micro-Cinderella Based on Self-Propelled Micromagnets for the Active Separation of Paramagnetic Particles Chem. Commun. 2013, 49, 5147-5149 10.1039/c3cc41962b
7. Zhao, G.; Pumera, M. Magnetotactic Artificial Self-Propelled Nanojets Langmuir 2013, 29, 7411-7415 10.1021/la303762a
8. Solovev, A. A.; Sanchez, S.; Pumera, M.; Mei, Y. F.; Schmidt, O. G. Magnetic Control of Tubular Catalytic Microbots for the Transport, Assembly, and Delivery of Micro-objects Adv. Funct. Mater. 2010, 20, 2430-2435 10.1002/adfm.200902376
9. Xu, T.; Soto, F.; Gao, W.; Garcia-Gradilla, V.; Li, J.; Zhang, X.; Wang, J. Ultrasound-Modulated Bubble Propulsion of Chemically Powered Microengines J. Am. Chem. Soc. 2014, 136, 8552-8555 10.1021/ja504150e
10. Ibele, M.; Mallouk, T. E.; Sen, A. Schooling Behavior of Light-Powered Autonomous Micromotors in Water Angew. Chem., Int. Ed. 2009, 48, 3308-3312 10.1002/anie.200804704
11. Wu, Z.; Lin, X.; Wu, Y.; Si, T.; Sun, J.; He, Q. Near-Infrared Light-Triggered "On/Off" Motion of Polymer Multilayer Rockets ACS Nano 2014, 8, 6097-6105 10.1021/nn501407r
12. 2 Tubular Microengines with Motion Controlled by Light-Induced Bubbles Small 2015, 11, 2564-2570 10.1002/smll.201403372
13. Li, J.; Singh, V. V.; Sattayasamitsathit, S.; Orozco, J.; Kaufmann, K.; Dong, R.; Gao, W.; Jurado-Sanchez, B.; Fedorak, Y.; Wang, J. Water-Driven Micromotors for Rapid Photocatalytic Degradation of Biological and Chemical Warfare Agents ACS Nano 2014, 8, 11118-11125 10.1021/nn505029k
14. Solovev, A. A.; Smith, E. J.; Bof ' Bufon, C. C.; Sanchez, S.; Schmidt, O. G. Light-Controlled Propulsion of Catalytic Microengines Angew. Chem., Int. Ed. 2011, 50, 10875-10878 10.1002/anie.201102096
15. Sanchez, S.; Ananth, A. N.; Fomin, V. M.; Viehrig, M.; Schmidt, O. G. Superfast Motion of Catalytic Microjet Engines at Physiological Temperature J. Am. Chem. Soc. 2011, 133, 14860-14863 10.1021/ja205012j
16. Soler, L.; Martinez-Cisneros, C.; Swiersy, A.; Sanchez, S.; Schmidt, O. G. Thermal Activation of Catalytic Microjets in Blood Samples Using Microfluidic Chips Lab Chip 2013, 13, 4299-4303 10.1039/c3lc50756d
17. Magdanz, V.; Stoychev, G.; Ionov, L.; Sanchez, S.; Schmidt, O. G. Stimuli-Responsive Microjets with Reconfigurable Shape Angew. Chem., Int. Ed. 2014, 53, 2673-2677 10.1002/anie.201308610
18. Sánchez, S.; Soler, L.; Katuri, J. Chemically Powered Micro- and Nanomotors Angew. Chem., Int. Ed. 2015, 54, 1414-1444 10.1002/anie.201406096
19. Sengupta, S.; Ibele, M. E.; Sen, A. Fantastic Voyage: Designing Self-Powered Nanorobots Angew. Chem., Int. Ed. 2012, 51, 8434-8445 10.1002/anie.201202044
20. Klajn, R. Spiropyran-Based Dynamic Materials Chem. Soc. Rev. 2014, 43, 148-184 10.1039/C3CS60181A
21. Bohaty, A.; Newton, M.; Zharov, I. Light-Controlled Ion Transport through Spiropyran-Modified Nanoporous Silica Colloidal Films J. Porous Mater. 2010, 17, 465-473 10.1007/s10934-009-9309-0
22. Zhao, G.; Seah, T. H.; Pumera, M. External-Energy-Independent Polymer Capsule Motors and Their Cooperative Behaviors Chem.-Eur. J. 2011, 17, 12020-12026 10.1002/chem.201101450
23. Lee, H.-i.; Wu, W.; Oh, J. K.; Mueller, L.; Sherwood, G.; Peteanu, L.; Kowalewski, T.; Matyjaszewski, K. Light-Induced Reversible Formation of Polymeric Micelles Angew. Chem., Int. Ed. 2007, 46, 2453-2457 10.1002/anie.200604278
24. Zhao, G.; Wang, H.; Khezri, B.; Webster, R. D.; Pumera, M. Influence of Real-World Environments on the Motion of Catalytic Bubble-Propelled Micromotors Lab Chip 2013, 13, 2937-2941 10.1039/c3lc50446h
25. Wang, H.; Zhao, G.; Pumera, M. Blood Proteins Strongly Reduce the Mobility of Artificial Self-Propelled Micromotors Chem.-Eur. J. 2013, 19, 16756-16759 10.1002/chem.201301906
26. Wang, H.; Zhao, G.; Pumera, M. Blood Metabolite Strongly Suppresses Motion of Electrochemically Deposited Catalytic Self-Propelled Microjet Engines Electrochem. Commun. 2014, 38, 128-130 10.1016/j.elecom.2013.11.013
27. Zhao, G.; Viehrig, M.; Pumera, M. Challenges of the Movement of Catalytic Micromotors in Blood Lab Chip 2013, 13, 1930-1936 10.1039/c3lc41423j
28. Gao, W.; Sattayasamitsathit, S.; Orozco, J.; Wang, J. Efficient Bubble Propulsion of Polymer-Based Microengines in Real-Life Environments Nanoscale 2013, 5, 8909-8914 10.1039/c3nr03254j
29. Wang, H.; Zhao, G.; Pumera, M. Blood Electrolytes Exhibit a Strong Influence on the Mobility of Artificial Catalytic Microengines Phys. Chem. Chem. Phys. 2013, 15, 17277-17280 10.1039/c3cp52726c
30. 2+ in Water Chem.-Eur. J. 2014, 20, 4292-4296 10.1002/chem.201304804
31. Wang, H.; Zhao, G.; Pumera, M. Crucial Role of Surfactants in Bubble-Propelled Microengines J. Phys. Chem. C 2014, 118, 5268-5274 10.1021/jp410003e
32. Simmchen, J.; Magdanz, V.; Sanchez, S.; Chokmaviroj, S.; Ruiz-Molina, D.; Baeza, A.; Schmidt, O. G. Effect Of Surfactants on the Performance of Tubular and Spherical Micromotors-A Comparative Study RSC Adv. 2014, 4, 20334-20340 10.1039/C4RA02202E
33. Zhao, G.; Pumera, M. Concentric Bimetallic Microjets by Electrodeposition RSC Adv. 2013, 3, 3963-3966 10.1039/c3ra23128c
34. Manesh, K. M.; Cardona, M.; Yuan, R.; Clark, M.; Kagan, D.; Balasubramanian, S.; Wang, J. Template-Assisted Fabrication of Salt-Independent Catalytic Tubular Microengines ACS Nano 2010, 4, 1799-1804 10.1021/nn1000468
35. Gao, W.; Sattayasamitsathit, S.; Wang, J. Catalytically Propelled Micro-/Nanomotors: How Fast Can They Move? Chem. Rec. 2012, 12, 224-231 10.1002/tcr.201100031
36. Solovev, A. A.; Mei, Y.; Bermúdez Ureña, E.; Huang, G.; Schmidt, O. G. Catalytic Microtubular Jet Engines Self-Propelled by Accumulated Gas Bubbles Small 2009, 5, 1688-1692 10.1002/smll.200900021
37. Li, J.; Huang, G.; Ye, M.; Li, M.; Liu, R.; Mei, Y. Dynamics of Catalytic Tubular Microjet Engines: Dependence on Geometry and Chemical Environment Nanoscale 2011, 3, 5083-5089 10.1039/c1nr10840a
38. Tyer, N. W.; Becker, R. S. Photochromic Spiropyrans. I. Absorption Spectra and Evaluation of the π-Electron Orthogonality of the Constituent Halves J. Am. Chem. Soc. 1970, 92, 1289-1294 10.1021/ja00708a031
39. Moniruzzaman, M.; Sabey, C. J.; Fernando, G. F. Photoresponsive Polymers: An Investigation of Their Photoinduced Temperature Changes During Photoviscosity Measurements Polymer 2007, 48, 255-263 10.1016/j.polymer.2006.08.066
40. Swansburg, S.; Buncel, E.; Lemieux, R. P. Thermal Racemization of Substituted Indolinobenzospiropyrans: Evidence of Competing Polar and Nonpolar Mechanisms J. Am. Chem. Soc. 2000, 122, 6594-6600 10.1021/ja0001613
41. Song, X.; Zhou, J.; Li, Y.; Tang, Y. Correlations between Solvatochromism, Lewis Acid-Base Equilibrium And Photochromism of an Indoline Spiropyran J. Photochem. Photobiol., A 1995, 92, 99-103 10.1016/1010-6030(95)04164-5
42. Rosario, R.; Gust, D.; Hayes, M.; Springer, J.; Garcia, A. A. Solvatochromic Study of the Microenvironment of Surface-Bound Spiropyrans Langmuir 2003, 19, 8801-8806 10.1021/la0344332
43. Berman, E.; Fox, R. E.; Thomson, F. D. Photochromic Spiropyrans. I. The Effect of Substituents on the Rate of Ring Closure J. Am. Chem. Soc. 1959, 81, 5605-5608 10.1021/ja01530a021
44. Vlassiouk, I.; Park, C.-D.; Vail, S. A.; Gust, D.; Smirnov, S. Control of Nanopore Wetting by a Photochromic Spiropyran: A Light-Controlled Valve and Electrical Switch Nano Lett. 2006, 6, 1013-1017 10.1021/nl060313d
45. Muñoz, M.; Rodríguez, A.; Graciani, M. d. M.; Moyá, M. L. Conductometric, Surface Tension, and Kinetic Studies in Mixed SDS-Tween 20 and SDS-SB3-12 Micellar Solutions Langmuir 2004, 20, 10858-10867 10.1021/la048247n
46. Corrin, M. L.; Harkins, W. D. The Effect of Salts on the Critical Concentration for the Formation of Micelles in Colloidal Electrolytes1 J. Am. Chem. Soc. 1947, 69, 683-688 10.1021/ja01195a065
47. Emerson, M. F.; Holtzer, A. On the Ionic Strength Dependence of Micelle Number. II J. Phys. Chem. 1967, 71, 1898-1907 10.1021/j100865a057
48. Liu, X.; Abbott, N. L. Spatial and Temporal Control of Surfactant Systems J. Colloid Interface Sci. 2009, 339, 1-18 10.1016/j.jcis.2009.07.006
49. Xu, Q.; Nakajima, M.; Ichikawa, S.; Nakamura, N.; Roy, P.; Okadome, H.; Shiina, T. Effects of Surfactant and Electrolyte Concentrations on Bubble Formation and Stabilization J. Colloid Interface Sci. 2009, 332, 208-214 10.1016/j.jcis.2008.12.044
50. ábrahám, á.; Kardos, A.; Mezei, A.; Campbell, R. A.; Varga, I. Effects of Ionic Strength on the Surface Tension and Nonequilibrium Interfacial Characteristics of Poly(sodium styrenesulfonate)/Dodecyltrimethylammonium Bromide Mixtures Langmuir 2014, 30, 4970-4979 10.1021/la500637v
51. Chang, C.-H.; Franses, E. I. Adsorption Dynamics of Surfactants at the Air/Water Interface: A Critical Review of Mathematical Models, Data, And Mechanisms Colloids Surf., A 1995, 100, 1-45 10.1016/0927-7757(94)03061-4
52. Lin, S.-Y.; McKeigue, K.; Maldarelli, C. Diffusion-Controlled Surfactant Adsorption Studied by Pendant Drop Digitization AIChE J. 1990, 36, 1785-1795 10.1002/aic.690361202
53. Eastoe, J.; Dalton, J. S. Dynamic Surface Tension and Adsorption Mechanisms of Surfactants at the Air-Water Interface Adv. Colloid Interface Sci. 2000, 85, 103-144 10.1016/S0001-8686(99)00017-2
54. Vazquez, G.; Alvarez, E.; Navaza, J. M. Surface Tension of Alcohol Water + Water from 20 to 50 °C J. Chem. Eng. Data 1995, 40, 611-614 10.1021/je00019a016
55. Zhao, G.; Stuart, E. J.; Pumera, M. Enhanced Diffusion of Pollutants by Self-Propulsion Phys. Chem. Chem. Phys. 2011, 13, 12755-12757 10.1039/c1cp21237k
56. Xiao, M.; Jiang, C.; Shi, F. Design of a UV-Responsive Microactuator on a Smart Device for Light-Induced ON-OFF-ON Motion NPG Asia Mater. 2014, 6, e128 10.1038/am.2014.76
57. Berkovic, G.; Krongauz, V.; Weiss, V. Spiropyrans and Spirooxazines for Memories and Switches Chem. Rev. 2000, 100, 1741-1754 10.1021/cr9800715
58. Kundu, P. K.; Samanta, D.; Leizrowice, R.; Margulis, B.; Zhao, H.; Börner, M.; Udayabhaskararao, T.; Manna, D.; Klajn, R. Light-Controlled Self-Assembly of Non-Photoresponsive Nanoparticles Nat. Chem. 2015, 7, 646-652 10.1038/nchem.2303
59. Karube, I.; Ishimori, Y.; Suzuki, S.; Sato, T. Photocontrol of Affinity Chromatography: Purification of Asparaginase by Photosensitive AHA-Gel Biotechnol. Bioeng. 1978, 20, 1775-1783 10.1002/bit.260201107
60. Rosario, R.; Gust, D.; Garcia, A. A.; Hayes, M.; Taraci, J. L.; Clement, T.; Dailey, J. W.; Picraux, S. T. Lotus Effect Amplifies Light-Induced Contact Angle Switching J. Phys. Chem. B 2004, 108, 12640-12642 10.1021/jp0473568
61. Rosario, R.; Gust, D.; Hayes, M.; Jahnke, F.; Springer, J.; Garcia, A. A. Photon-Modulated Wettability Changes on Spiropyran-Coated Surfaces Langmuir 2002, 18, 8062-8069 10.1021/la025963l
62. Baillet, G.; Campredon, M.; Guglielmetti, R.; Giusti, G.; Aubert, C. Dealkylation of N-Substituted Indolinospironaphthoxazine Photochromic Compounds under UV Irradiation J. Photochem. Photobiol., A 1994, 83, 147-151 10.1016/1010-6030(94)03816-3
63. Baillet, G.; Giusti, G.; Guglielmetti, R. Comparative Photodegradation Study between Spiro[Indoline-Oxazine] and Spiro[Indoline-Pyran] Derivatives in Solution J. Photochem. Photobiol., A 1993, 70, 157-161 10.1016/1010-6030(93)85036-8
64. Hall, R. A.; Thistlethwaite, P. J.; Grieser, F.; Kimizuka, N.; Kunitake, T. Acid-Base Equilibria of Merocyanine Air-Water Monolayers Langmuir 1994, 10, 3743-3748 10.1021/la00022a058
65. Wu, Y.; Qu, X.; Huang, L.; Qiu, D.; Zhang, C.; Liu, Z.; Yang, Z.; Feng, L. Optically Switchable Organic Hollow Nanocapsules J. Colloid Interface Sci. 2010, 343, 155-161 10.1016/j.jcis.2009.11.041
66. Zhu, M.-Q.; Zhu, L.; Han, J. J.; Wu, W.; Hurst, J. K.; Li, A. D. Q. Spiropyran-Based Photochromic Polymer Nanoparticles with Optically Switchable Luminescence J. Am. Chem. Soc. 2006, 128, 4303-4309 10.1021/ja0567642
67. Satoh, T.; Sumaru, K.; Takagi, T.; Takai, K.; Kanamori, T. Isomerization of Spirobenzopyrans Bearing Electron-Donating and Electron-Withdrawing Groups in Acidic Aqueous Solutions Phys. Chem. Chem. Phys. 2011, 13, 7322-7329 10.1039/c0cp01989e
68. Tomioka, H.; Itoh, T. Photochromism of Spiropyrans in Organized Molecular Assemblies. Formation of J- And H-Aggregates of Photomerocyanines in Bilayers-Clay Matrices J. Chem. Soc., Chem. Commun. 1991, 532-533 10.1039/c39910000532
69. Wu, Y.; Zhang, C.; Qu, X.; Liu, Z.; Yang, Z. Light-Triggered Reversible Phase Transfer of Composite Colloids Langmuir 2010, 26, 9442-9448 10.1021/la100458j
70. Krongauz, V. A.; Goldburt, E. S. Quasi-Crystals from Irradiated Photochromic Dyes in an Applied Electric Field Nature 1978, 271, 43-45 10.1038/271043a0
71. Cabrera, I.; Shvartsman, F.; Veinberg, O.; Krongauz, V. Photocontraction of Liquid Spiropyran-Merocyanine Films Science 1984, 226, 341-343 10.1126/science.226.4672.341
72. Samanta, S.; Locklin, J. Formation of Photochromic Spiropyran Polymer Brushes via Surface-Initiated, Ring-Opening Metathesis Polymerization: Reversible Photocontrol of Wetting Behavior and Solvent Dependent Morphology Changes Langmuir 2008, 24, 9558-9565 10.1021/la8017387
73. McCoy, C. P.; Donnelly, L.; Jones, D. S.; Gorman, S. P. Synthesis and Characterisation of Polymerisable Photochromic Spiropyrans: Towards Photomechanical Biomaterials Tetrahedron Lett. 2007, 48, 657-661 10.1016/j.tetlet.2006.11.110
74. Eckhardt, H.; Bose, A.; Krongauz, V. A. Formation of Molecular H- And J-Stacks by the Spiropyran-Merocyanine Transformation in a Polymer Matrix Polymer 1987, 28, 1959-1964 10.1016/0032-3861(87)90306-5
75. Seki, T.; Ichimura, K. Formation of Head-To-Tail and Side-By-Side Aggregates of Photochromic Spiropyrans in Bilayer Membrane J. Phys. Chem. 1990, 94, 3769-3775 10.1021/j100372a077
76. Son, S.; Shin, E.; Kim, B.-S. Light-Responsive Micelles of Spiropyran Initiated Hyperbranched Polyglycerol for Smart Drug Delivery Biomacromolecules 2014, 15, 628-634 10.1021/bm401670t
77. Raymo, F. M.; Giordani, S. Signal Processing at the Molecular Level J. Am. Chem. Soc. 2001, 123, 4651-4652 10.1021/ja005699n
78. Wojtyk, J. T. C.; Wasey, A.; Xiao, N.-N.; Kazmaier, P. M.; Hoz, S.; Yu, C.; Lemieux, R. P.; Buncel, E. Elucidating the Mechanisms of Acidochromic Spiropyran-Merocyanine Interconversion J. Phys. Chem. A 2007, 111, 2511-2516 10.1021/jp068575r
79. Keum, S.-R.; Roh, S.-J.; Ahn, S.-M.; Lim, S.-S.; Kim, S.-H.; Koh, K. Solvatochromic Behavior of Non-Activated Indolinobenzospiropyran 6-Carboxylates in Aqueous Binary Solvent Mixtures. Part II 1 Dyes Pigm. 2007, 74, 343-347 10.1016/j.dyepig.2006.02.013
80. Lenoble, C.; Becker, R. S. Photophysics, Photochemistry, Kinetics, and Mechanism of the Photochromism of 6′-Nitroindolinospiropyran J. Phys. Chem. 1986, 90, 62-65 10.1021/j100273a015
81. Minkin, V. I. Photo-, Thermo-, Solvato-, and Electrochromic Spiroheterocyclic Compounds Chem. Rev. 2004, 104, 2751-2776 10.1021/cr020088u
82. Mar Blanca, C.; Hell, S. W. Sharp Spherical Focal Spot by Dark Ring 4Pi-Confocal Microscopy Single Mol. 2001, 2, 207-210 10.1002/1438-5171(200110)2:3<207::AID-SIMO207>3.0.CO;2-S