Tailoring the properties of surface-immobilized azobenzenes by monolayer dilution and surface curvature

Langmuir

Volumn 31, Issue 3, 2015, Pages 1048-1057

  Moldt, Thomas ^a   Brete, Daniel ^a   Przyrembel, Daniel ^a   Das, Sanjib ^b,c   Goldman, Joel R ^b   Kundu, Pintu K ^b   Gahl, Cornelius ^a   Klajn, Rafal ^b   Weinelt, Martin ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^c CSIR Institute of Minerals and Materials Technology   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMOPHORES; EXCITED STATES; LIGHT SOURCES; MONOLAYERS; SELF ASSEMBLED MONOLAYERS; X RAY SPECTROSCOPY;

EXCITONIC COUPLING; GOLD NANOPARTICLES; OPTICAL SPECTROSCOPY; PLANAR SUBSTRATE; SHORT TIME SCALE; STERIC CONSTRAINT; SURFACE CURVATURES; UPRIGHT POSITION;

AZOBENZENE;

EID: 84921804736     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la504291n     Document Type: Article

References (62)

1. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology Chem. Rev. 2005, 105, 1103-1169
2. Ulman, A. Formation and Structure of Self-Assembled Monolayers Chem. Rev. 1996, 96, 1533-1554
3. DiBenedetto, S. A.; Facchetti, A.; Ratner, M. A.; Marks, T. J. Molecular Self-Assembled Monolayers and Multilayers for Organic and Unconventional Inorganic Thin-Film Transistor Applications Adv. Mater. 2009, 21, 1407-1433
4. Samanta, D.; Sarkar, A. Immobilization of Bio-macromolecules on Self-Assembled Monolayers: Methods and Sensor Applications Chem. Soc. Rev. 2011, 40, 2567-2592
5. Smaali, K.; Lenfant, S.; Karpe, S.; Oçafrain, M.; Blanchard, P.; Deresmes, D.; Godey, S.; Rochefort, A.; Roncali, J.; Vuillaume, D. High On-Off Conductance Switching Ratio in Optically-Driven Self-Assembled Conjugated Molecular Systems ACS Nano 2010, 4, 2411-2421
6. Yang, H.; Yuan, B.; Zhang, X.; Scherman, O. A. Supramolecular Chemistry at Interfaces: Host-Guest Interactions for Fabricating Multifunctional Biointerfaces Acc. Chem. Res. 2014, 47, 2106-2115
7. Feringa, B. L. Molecular Electronics; Wiley: Weinheim, 2001.
8. Ferri, V.; Elbing, M.; Pace, G.; Dickey, M. D.; Zharnikov, M.; Samorì, P.; Mayor, M.; Rampi, M. A. Light-Powered Electrical Switch Based on Cargo-Lifting Azobenzene Monolayers Angew. Chem., Int. Ed. 2008, 47, 3407-3409
9. Crivillers, N. Photoinduced Work Function Changes by Isomerization of a Densely Packed Azobenzene-Based SAM on Au: A Joint Experimental and Theoretical Study Phys. Chem. Chem. Phys. 2011, 13, 14302-14310
10. García-Amorós, J.; Velasco, D. Recent Advances Towards Azobenzene-Based Light-Driven Real-Time Information-Transmitting Materials Beilstein J. Org. Chem. 2012, 8, 1003-1017
11. Kriegisch, V.; Lambert, C. Self-Assembled Monolayers of Chromophores on Gold Surfaces Top. Curr. Chem. 2005, 258, 257-313
12. Bandara, H. M. D.; Burdette, S. C. Photoisomerization in Different Classes of Azobenzene Chem. Soc. Rev. 2012, 41, 1809-1825
13. Klajn, R. Immobilized Azobenzenes for the Construction of Photoresponsive Materials Pure Appl. Chem. 2010, 82, 2247-2279
14. Wolf, M.; Tegeder, P. Reversible Molecular Switching at a Metal Surface: A Case Study of Tetra-tert-butyl-azobenzene on Au(111) Surf. Sci. 2009, 603, 1506-1517
15. Schmidt, R.; Hagen, S.; Brete, D.; Carley, R.; Gahl, C.; Dokić, J.; Saalfrank, P.; Hecht, S.; Tegeder, P.; Weinelt, M. On the Electronic and Geometrical Structure of the Trans- and Cis-Isomer of Tetra-tert-butyl-azobenzene on Au(111) Phys. Chem. Chem. Phys. 2010, 12, 4488-4497
16. Muntwiler, M.; Lindstrom, C. D.; Zhu, X. Y. Delocalized Electron Resonance at the Alkanethiolate Self-Assembled Monolayer/Au(111) Interface J. Chem. Phys. 2006, 124, 081104
17. Bent, S. F. Heads or Tails: Which Is More Important in Molecular Self-Assembly? ACS Nano 2007, 1, 10-12
18. Freyer, W.; Brete, D.; Schmidt, R.; Gahl, C.; Carley, R.; Weinelt, M. Switching Behavior and Optical Absorbance of Azobenzene-Functionalized Alkanethiols in Different Environments J. Photochem. Photobiol., A 2009, 204, 102-109
19. Gahl, C.; Schmidt, R.; Brete, D.; McNellis, E. R.; Freyer, W.; Carley, R.; Reuter, K.; Weinelt, M. Structure and Excitonic Coupling in Self-Assembled Monolayers of Azobenzene-Functionalized Alkanethiols J. Am. Chem. Soc. 2010, 132, 1831-1838
20. Kasha, M. Energy Transfer Mechanisms and the Molecular Exciton Model for Molecular Aggregates Radiat. Res. 1963, 20, 55-70
21. Utecht, M.; Klamroth, T.; Saalfrank, P. Optical Absorption and Excitonic Coupling in Azobenzenes Forming Self-Assembled Monolayers: A Study Based on Densitiy Functional Theory Phys. Chem. Chem. Phys. 2011, 13, 21608-21614
22. Heinemann, N.; Grunau, J.; Leißner, T.; Andreyev, O.; Kuhn, S.; Jung, U.; Zargarani, D.; Herges, R.; Magnussen, O.; Bauer, M. Reversible Switching in Self-Assembled Monolayers of Azobenzene Thiolates on Au (111) Probed by Threshold Photoemission Chem. Phys. 2012, 402, 22-28
23. Shin, K.; Shin, E. J. Photoresponsive Azobenzene-Modified Gold Nanoparticle Bull. Korean Chem. Soc. 2008, 29, 1259-1262
24. Suda, M.; Kameyama, N.; Suzuki, M.; Kawamura, N.; Einaga, Y. Reversible Phototuning of Ferromagnetism at Au-S Interfaces at Room Temperature Angew. Chem., Int. Ed. 2008, 47, 160-163
25. Caldwell, W. B.; Campbell, D. J.; Chen, K.; Herr, B. R.; Mirkin, C. A.; Malik, A.; Durbin, M. K.; Dutta, P.; Huang, K. G. A Highly Ordered Self-Assembled Monolayer Film of an Azobenzenealkanethiol on Au (111): Electrochemical Properties and Structural Characterization by Synchrotron in-Plane X-ray Diffraction, Atomic Force Microscopy, and Surface-Enhanced Raman Spectroscopy J. Am. Chem. Soc. 1995, 117, 6071-6082
26. Klajn, R.; Wesson, P. J.; Bishop, K. J. M.; Grzybowski, B. A. Writing Self-Erasing Images Using Metastable Nanoparticle "Inks" Angew. Chem., Int. Ed. 2009, 48, 7035-7039
27. Ely, T.; Das, S.; Li, W.; Kundu, P. K.; Tirosh, E.; Cahen, D.; Vilan, A.; Klajn, R. Photocontrol of Electrical Conductance with a Nonsymmetrical Azobenzene Dithiol Synlett 2013, 24, 2370-2374
28. Nagahiro, T.; Akiyama, H.; Hara, M.; Tamada, K. Photoisomerization of Azobenzene Containing Self-Assembled Monolayers Investigated by Kelvin Probe Work Function Measurements J. Electron Spectrosc. Relat. Phenom. 2009, 172, 128-133
29. Jung, U.; Filinova, O.; Kuhn, S.; Zargarani, D.; Bornholdt, C.; Herges, R.; Magnussen, O. Photoswitching Behavior of Azobenzene-Containing Alkanethiol Self-Assembled Monolayers on Au Surfaces Langmuir 2010, 26, 13913-13923
30. Imabayashi, S.; Gon, N.; Sasaki, T.; Hobara, D.; Kakiuchi, T. Effect of Nanometer-Scale Phase Separation on Wetting of Binary Self-Assembled Thiol Monolayers on Au(111) Langmuir 1998, 14, 2348-2351
31. Pace, G.; Petitjean, A.; Lalloz-Vogel, M.-N.; Harrowfield, J.; Lehn, J.-M.; Samorì, P. Subnanometer-Resolved Patterning of Bicomponent Self-Assembled Monolayers on Au(111) Angew. Chem., Int. Ed. 2008, 47, 2484-2488
32. Chen, S.; Li, L.; Boozer, C. L.; Jiang, S. Controlled Chemical and Structural Properties of Mixed Self-Assembled Monolayers by Coadsorption of Symmetric and Asymmetric Disulfides on Au (111) J. Phys. Chem. B 2001, 105, 2975-2980
33. Evans, S. D.; Johnson, S. R.; Ringsdorf, H.; Williams, L. M.; Wolf, H. Photoswitching of Azobenzene Derivatives Formed on Planar and Colloidal Surfaces Langmuir 1998, 14, 6436-6440
34. Wan, P.; Xing, Y.; Chen, Y.; Chi, L.; Zhang, X. Host-Guest Chemistry at Interface for Photoswitchable Bioelectrocatalysis Chem. Commun. 2011, 47, 5994-5996
35. Valley, D. T.; Onstott, M.; Malyk, S.; Benderskii, A. V. Steric Hindrance of Photoswitching in Self-Assembled Monolayers of Azobenzene and Alkane Thiols Langmuir 2013, 29, 11623-11631
36. Kumar, A. S.; Ye, T.; Takami, T.; Yu, B.-C.; Flatt, A. K.; Tour, J. M.; Weiss, P. S. Reversible Photo-Switching of Single Azobenzene Molecules in Controlled Nanoscale Environments Nano Lett. 2008, 8, 1644-1648
37. Zheng, Y. B.; Payton, J. L.; Chung, C.-H.; Liu, R.; Cheunkar, S.; Pathem, B. K.; Yang, Y.; Jensen, L.; Weiss, P. S. Surface-Enhanced Raman Spectroscopy to Probe Reversibly Photoswitchable Azobenzene in Controlled Nanoscale Environments Nano Lett. 2011, 11, 3447-3452
38. Zdobinsky, T.; Maiti, S. P.; Klajn, R. Support Curvature and Conformational Freedom Control Chemical Reactivity of Immobilized Species J. Am. Chem. Soc. 2014, 136, 2711-2714
39. Klajn, R.; Bishop, K. J. M.; Grzybowski, B. A. Light-Controlled Self-Assembly of Reversible and Irreversible Nanoparticle Suprastructures Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 10305-10309
40. Das, S.; Ranjan, P.; Maiti, P. S.; Singh, G.; Leitus, G.; Klajn, R. Dual-Responsive Nanoparticles and their Self-Assembly Adv. Mater. 2013, 25, 422-426
41. Chovnik, O.; Balgley, R.; Goldman, J. R.; Klajn, R. Dynamically Self-Assembling Carriers Enable Guiding of Diamagnetic Particles by Weak Magnets J. Am. Chem. Soc. 2012, 134, 19564-19567
42. Kowalczyk, P. High Temperature STM/STS Investigations of Resonant Image States on Au(1 1 1) Appl. Surf. Sci. 2007, 253, 4036-4040
43. Jaschke, M.; Schönherr, H.; Wolf, H.; Butt, H.-J.; Bamberg, E.; Besocke, M. K.; Ringsdorf, H. Structure of Alkyl and Perfluoroalkyl Disulfide and Azobenzenethiol Monolayers on Gold(111) Revealed by Atomic Force Microscopy J. Phys. Chem. 1996, 100, 2290-2301
44. Seah, M. P.; Gilmore, I. S.; Beamson, G. XPS: Binding Energy Calibration of Electron Spectrometers-Re-evaluation of the Reference Energies Surf. Interface Anal. 1998, 26, 642-649
45. Shirley, D. A. High-Resolution X-ray Photoemission Spectrum of the Valance Bands of Gold Phys. Rev. B: Condens. Matter Mater. Phys. 1972, 5, 4709-4714
46. Daniel, M.-C.; Astruc, D. Gold Nanoparticles: Assembly, Supramolecular Chemistry, Quantum-Size-Related Properties, and Applications toward Biology, Catalysis, and Nanotechnology Chem. Rev. 2004, 104, 293-346
47. Myroshnychenko, V.; Rodríguez-Fernández, J.; Pastoriza-Santos, I.; Funston, A. M.; Novo, C.; Mulvaney, P.; Liz-Marzán, L. M.; García de Abajo, F. J. Modelling the Optical Response of Gold Nanoparticles Chem. Soc. Rev. 2008, 37, 1792-1805
48. Fabris, L.; Antonello, S.; Armelao, L.; Donkers, R. L.; Polo, F.; Toniolo, C.; Maran, F. Gold Nanoclusters Protected by Conformationally Constrained Peptides J. Am. Chem. Soc. 2006, 128, 326-336
49. Badia, A.; Singh, S.; Demers, L.; Cuccia, L.; Brown, G. R.; Lennox, R. B. Self-Assembled Monolayers on Gold Nanoparticles Chem.-Eur. J. 1996, 2, 359-363
50. Brete, D.; Przyrembel, D.; Eickhoff, C.; Carley, R.; Freyer, W.; Reuter, K.; Gahl, C.; Weinelt, M. Mixed Self-Assembled Monolayers of Azobenzene Photoswitches with Trifluoromethyl and Cyano End Groups J. Phys.: Condens. Matter 2012, 24, 394015
51. Wolf, H.; Ringsdorf, H.; Delamarche, E.; Takami, T.; Kang, H.; Michel, B.; Gerber, C.; Jaschke, M.; Butt, H.-J.; Bamberg, E. End-Group-Dominated Molecular Order in Self-Assembled Monolayers J. Phys. Chem. 1995, 99, 7102-7107
52. Stöhr, J.; Outka, D. A. Determination of Molecular Orientation on Surfaces from the Angular Dependence of near-Edge X-Ray-Absorption Fine-Structure Spectra Phys. Rev. B: Condens. Matter Mater. Phys. 1987, 36, 7891-7905
53. Cyganik, P.; Buck, M.; Strunskus, T.; Shaporenko, A.; Wilton-Ely, J. D. E. T.; Zharnikov, M.; Wöll, C. Competition as a Design Concept: Polymorphism in Self-Assembled Monolayers of Biphenyl-Based Thiols J. Am. Chem. Soc. 2006, 128, 13868-13878
54. Rau, H. In Photochromism; Dürr, H.; Bouas-Laurent, H., Eds.; Elsevier Science: Amsterdam, 2003; Chapter 4, pp 165-192.
55. Conti, I.; Garavelli, M.; Orlandi, G. The Different Photoisomerization Efficiency of Azobenzene in the Lowest n pi∗ and pi pi∗ Singlets: The Role of a Phantom State J. Am. Chem. Soc. 2008, 130, 5216-5230
56. Wang, R.; Iyoda, T.; Jiang, L.; Tryk, D. A.; Hashimoto, K.; Fujishima, A. Structural Investigation of Azobenzene-Containing Self-Assembled Monolayer Films J. Electroanal. Chem. 1997, 438, 213-219
57. Han, M.; Honda, T.; Ishikawa, D.; Ito, E.; Hara, M.; Norikane, Y. Realization of Highly Photoresponsive Azobenzene-Functionalized Monolayers J. Mater. Chem. 2011, 21, 4696-4702
58. Kuhn, H.; Kuhn, C. In J-Aggregates; Kobayashi, T., Ed.; World Scientific: Singapore, 1996; Chapter 1, pp 1-40.
59. Eisfeld, A.; Briggs, J. S. The J- and H-Bands of Organic Dye Aggregates Chem. Phys. 2006, 324, 376-384
60. Pace, G.; Ferri, V.; Grave, C.; Elbing, M.; von Hanisch, C.; Zharnikov, M.; Mayor, M.; Rampi, M. A.; Samorì, P. Cooperative Light-Induced Molecular Movements of Highly Ordered Azobenzene Self-Assembled Monolayers Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 9937-9942
61. Pathem, B. K.; Claridge, S. A.; Zheng, Y. B.; Weiss, P. S. Molecular Switches and Motors on Surfaces Annu. Rev. Phys. Chem. 2013, 64, 605-630
62. Zheng, Y. B.; Pathem, B. K.; Hohman, J. N.; Thomas, J. C.; Kim, M.; Weiss, P. S. Photoresponsive Molecules in Well-Defined Nanoscale Environments Adv. Mater. 2012, 25, 302-312