Aerosolized droplet mediated self-assembly of photosynthetic pigment analogues and deposition onto substrates

ACS Nano

Volumn 8, Issue 2, 2014, Pages 1429-1438

  Shah, Vivek B ^a   Biswas, Pratim ^a  

^a WASHINGTON UNIVERSITY IN ST LOUIS   (United States)

Author keywords

aerosol route; bacteriochlorophyll analogues; chlorin; photosynthetic antenna; supramolecular self assembly

Indexed keywords

PIGMENT; SOLVENT;

AEROSOL; ARTICLE; CHEMISTRY; PHOTOSYNTHESIS;

AEROSOLS; PHOTOSYNTHESIS; PIGMENTS, BIOLOGICAL; SOLVENTS;

EID: 84894609910     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn405251h     Document Type: Article

References (51)

1. Peet, J.; Heeger, A. J.; Bazan, G. C. "Plastic" Solar Cells: Self-Assembly of Bulk Heterojunction Nanomaterials by Spontaneous Phase Separation Acc. Chem. Res. 2009, 42, 1700-1708
2. Tange, R.; Inai, K.; Sagawa, T.; Yoshikawa, S. Application of Self-Assembling Photosynthetic Dye for Organic Photovoltaics J. Mater. Res. 2011, 26, 306-310
3. Fiorini, C.; Charra, F. Self-Assembly: Mastering Photonic Processes at Nanoscale Opto-Electron. Rev. 2010, 18, 376-383
4. Tam, J. M.; Tam, J. O.; Murthy, A.; Ingram, D. R.; Ma, L. L.; Travis, K.; Johnston, K. P.; Sokolov, K. V. Controlled Assembly of Biodegradable Plasmonic Nanoclusters for near-Infrared Imaging and Therapeutic Applications ACS Nano 2010, 4, 2178-2184
5. Kim, D. H.; Lee, D. Y.; Lee, H. S.; Lee, W. H.; Kim, Y. H.; Han, J. I.; Cho, K. High-Mobility Organic Transistors Based on Single-Crystalline Microribbons of Triisopropylisilylethynl Pentacene via Solution-Phase Self-Assembly Adv. Mater. 2007, 19, 678-682
6. Palmer, R. E.; Robinson, A. P. G.; Guo, Q. How Nanoscience Translates into Technology: The Case of Self-Assembled Monolayers, Electron-Beam Writing, and Carbon Nanomembranes ACS Nano 2013, 7, 6416-6421
7. Lee, C.; Meteer, J.; Narayanan, V.; Kan, E. Self-Assembly of Metal Nanocrystals on Ultrathin Oxide for Nonvolatile Memory Applications J. Electron. Mater. 2005, 34, 1-11
8. Zhang, S. Fabrication of Novel Biomaterials through Molecular Self-Assembly Nat. Biotechnol. 2003, 21, 1171-1178
9. 2+ Fixed to Cation Exchange Polymer J. Mol. Catal. A: Chem. 2003, 193, 27-32
10. Schmidt-Mende, L.; Fechtenkotter, A.; Mullen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Self-Organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics Science 2001, 293, 1119-1122
11. De Rosa, C.; Park, C.; Thomas, E. L.; Lotz, B. Microdomain Patterns from Directional Eutectic Solidification and Epitaxy Nature 2000, 405, 433-437
12. Lindsey, J. S. Self-Assembly in Synthetic Routes to Molecular Devices. Biological Principles and Chemical Perspectives: A Review New J. Chem. 1991, 15, 153-180
13. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Molecular Self-Assembly and Nanochemistry-a Chemical Strategy for the Synthesis of Nanostructures Science 1991, 254, 1312-1319
14. Whitesides, G. M.; Grzybowski, B. Self-Assembly at All Scales Science 2002, 295, 2418-2421
15. Miras, H. N.; Wilson, E. F.; Cronin, L. Unravelling the Complexities of Inorganic and Supramolecular Self-Assembly in Solution with Electrospray and Cryospray Mass Spectrometry Chem. Commun. 2009, 1297-1311
16. Frigaard, N.-U.; Bryant, D. Chlorosomes: Antenna Organelles in Photosynthetic Green Bacteria. In Complex Intracellular Structures in Prokaryotes; Shively, J., Ed.; Springer: Berlin, 2006; Vol. 2, pp 79-114.
17. Overmann, J.; Cypionka, H.; Pfennig, N. An Extremely Low-Light-Adapted Phototrophic Sulfur Bacterium from the Black-Sea Limnol. Oceanogr. 1992, 37, 150-155
18. Blankenship, R. E. Molecular Mechanisms of Photosynthesis; Blackwell Science: Oxford, 2002.
19. 2 by Artificial Self-Assembling Mimics of the Natural Chlorosomal Bacteriochlorophylls J. Phys. Chem. C 2007, 111, 11726-11733
20. Modesto-Lopez, L. B.; Thimsen, E. J.; Collins, A. M.; Blankenship, R. E.; Biswas, P. Electrospray-Assisted Characterization and Deposition of Chlorosomes to Fabricate a Biomimetic Light-Harvesting Device Energy Env. Sci. 2010, 3, 216-222
21. Jelley, E. E. Spectral Absorption and Fluorescence of Dyes in the Molecular State Nature 1936, 138, 1009-1010
22. Mass, O.; Pandithavidana, D. R.; Ptaszek, M.; Santiago, K.; Springer, J. W.; Jiao, J.; Tang, Q.; Kirmaier, C.; Bocian, D. F.; Holten, D.; Lindsey, J. S. De Novo Synthesis and Properties of Analogues of the Self-Assembling Chlorosomal Bacteriochlorophylls New J. Chem. 2011, 35, 2671-2690
23. Huber, V.; Katterle, M.; Lysetska, M.; Würthner, F. Reversible Self-Organization of Semisynthetic Zinc Chlorins into Well-Defined Rod Antennae Angew. Chem., Int. Ed. 2005, 44, 3147-3151
24. Roger, C.; Muller, M. G.; Lysetska, M.; Miloslavina, Y.; Holzwarth, A. R.; Wurthner, F. Efficient Energy Transfer from Peripheral Chromophores to the Self-Assembled Zinc Chlorin Rod Antenna: A Bioinspired Light-Harvesting System to Bridge the "Green Gap" J. Am. Chem. Soc. 2006, 128, 6542-6543
25. Balaban, T. S. Tailoring Porphyrins and Chlorins for Self-Assembly in Biomimetic Artificial Antenna Systems Acc. Chem. Res. 2005, 38, 612-623
26. Miyatake, T.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Self-Assembly of Synthetic Zinc Chlorins in Aqueous Microheterogeneous Media to an Artificial Supramolecular Light-Harvesting Device Helv. Chim. Acta 1999, 82, 797-810
27. Shahar, C.; Baram, J.; Tidhar, Y.; Weissman, H.; Cohen, S. R.; Pinkas, I.; Rybtchinski, B. Self-Assembly of Light-Harvesting Crystalline Nanosheets in Aqueous Media ACS Nano 2013, 7, 3547-56
28. Miyatake, T.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Artificial Light-Harvesting Antennae: Singlet Excitation Energy Transfer from Zinc Chlorin Aggregate to Bacteriochlorin in Homogeneous Hexane Solution Photochem. Photobiol. 1999, 69, 448-456
29. Misawa, K.; Ono, H.; Minoshima, K.; Kobayashi, T. New Fabrication Method for Highly Oriented J-Aggregates Dispersed in Polymer-Films Appl. Phys. Lett. 1993, 63, 577-579
30. Mayerhoffer, U.; Wurthner, F. Halogen-Arene Interactions Assist in Self-Assembly of Dyes Angew. Chem., Int. Ed. 2012, 51, 5615-5619
31. Miyatake, T.; Tamiaki, H. Self-Aggregates of Natural Chlorophylls and Their Synthetic Analogues in Aqueous Media for Making Light-Harvesting Systems Coord. Chem. Rev. 2010, 254, 2593-2602
32. Horn, D.; Rieger, J. Organic Nanoparticles in the Aqueous Phase-Theory, Experiment, and Use Angew. Chem., Int. Ed. 2001, 40, 4330-4361
33. Numata, M.; Kinoshita, D.; Taniguchi, N.; Tamiaki, H.; Ohta, A. Self-Assembly of Amphiphilic Molecules in Droplet Compartments: An Approach toward Discrete Submicrometer-Sized One-Dimensional Structures Angew. Chem., Int. Ed. 2012, 51, 1844-1848
34. Mobius, D.; Kuhn, H. Energy-Transfer in Monolayers with Cyanine Dye Sheibe Aggregates J. Appl. Phys. 1988, 64, 5138-5141
35. Jiao, J.; Anariba, F.; Tiznado, H.; Schmidt, I.; Lindsey, J. S.; Zaera, F.; Bocian, D. F. Stepwise Formation and Characterization of Covalently Linked Multiporphyrin-Imide Architectures on Si(100) J. Am. Chem. Soc. 2006, 128, 6965-6974
36. Liu, Z.; Schmidt, I.; Thamyongkit, P.; Loewe, R. S.; Syomin, D.; Diers, J. R.; Zhao, Q.; Misra, V.; Lindsey, J. S.; Bocian, D. F. Synthesis and Film-Forming Properties of Ethynylporphyrins Chem. Mater. 2005, 17, 3728-3742
37. Lu, Y. F.; Fan, H. Y.; Stump, A.; Ward, T. L.; Rieker, T.; Brinker, C. J. Aerosol-Assisted Self-Assembly of Mesostructured Spherical Nanoparticles Nature 1999, 398, 223-226
38. Moon, J. H.; Yi, G. R.; Yang, S. M.; Pine, D. J.; Bin Park, S. Electrospray-Assisted Fabrication of Uniform Photonic Balls Adv. Mater. 2004, 16, 605-609
39. Lee, S. Y.; Gradon, L.; Janeczko, S.; Iskandar, F.; Okuyama, K. Formation of Highly Ordered Nanostructures by Drying Micrometer Colloidal Droplets ACS Nano 2010, 4, 4717-4724
40. 2 Photoreduction by Evaporation Driven Self-Assembly Catal. Sci. Technol. 2011, 1, 593-600
41. Wu, C.; Lee, D.; Zachariah, M. R. Aerosol-Based Self-Assembly of Nanoparticles into Solid or Hollow Mesospheres Langmuir 2010, 26, 4327-4330
42. Langley, G. J.; Hecquet, E.; Morris, I. P.; Hamilton, D. G. Direct Observation of Associative Behaviour by Electrospray Ionization: Self-Assembly-Fact or Fiction? Rapid Commun. Mass Spectrom. 1997, 11, 165-170
43. 4] Azolophanes: Associative Behaviour Revealed by Electrospray Ionization Rapid Commun. Mass Spectrom. 2000, 14, 1014-1016
44. Novoderezhkin, V.; Taisova, A.; Fetisova, Z. G. Unit Building Block of the Oligomeric Chlorosomal Antenna of the Green Photosynthetic Bacterium Chloroflexus aurantiacus: Modeling of Nonlinear Optical Spectra Chem. Phys. Lett. 2001, 335, 234-240
45. Muenter, A. A.; Brumbaugh, D. V.; Apolito, J.; Horn, L. A.; Spano, F. C.; Mukamel, S. Size Dependence of Excited-State Dynamics for J-Aggregates at Silver Bromide Interfaces J. Phys. Chem. 1992, 96, 2783-2790
46. Roden, J.; Strunz, W. T.; Eisfeld, A. Spectral Properties of Molecular Oligomers. A Non-Markovian Quantum State Diffusion Approach Int. J. Mod. Phys. B 2010, 24, 5060-5067
47. Basak, S.; Chen, D. R.; Biswas, P. Electrospray of Ionic Precursor Solutions to Synthesize Iron Oxide Nanoparticles: Modified Scaling Law Chem. Eng. Sci. 2007, 62, 1263-1268
48. Chen, D.-R.; Pui, D. Y. H. Experimental Investigation of Scaling Laws for Electrospraying: Dielectric Constant Effect Aerosol Sci. Technol. 1997, 27, 367-380
49. Kashchiev, D. Nucleation; Elsevier Science, 2000.
50. Chen, D. R.; Pui, D. Y. H.; Kaufman, S. L. Electrospraying of Conducting Liquids for Monodisperse Aerosol Generation in the 4 nm to 1.8 μm Range J. Aerosol Sci. 1995, 26, 963-978
51. Hinds, W. C. Aerosol Technology: Properties, Behavior, and Measurement of Airborne Particles, 2nd ed.; John Wiley & Sons, Inc.: New York, 1999.