A Photolithographic Approach to Spatially Resolved Cross-Linked Nanolayers

Langmuir

Volumn 31, Issue 10, 2015, Pages 3242-3253

  Fuchise, Keita ^a   Lindemann, Peter ^b   Heißler, Stefan ^b   Gliemann, Hartmut ^b   Trouillet, Vanessa ^a   Welle, Alexander ^a,b   Berson, Jonathan ^a,b   Walheim, Stefan ^a,b   Schimmel, Thomas ^a,b   Meier, Michael A R ^a   Barner Kowollik, Christopher ^a,b  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; ATOMIC FORCE MICROSCOPY; CRYSTAL ATOMIC STRUCTURE; ELECTRODEPOSITION; ELECTROSPRAY IONIZATION; FREE RADICAL POLYMERIZATION; FREE RADICALS; MASS SPECTROMETRY; NANOSHEETS; ORGANIC POLYMERS; PHOTOCHEMICAL REACTIONS; PHOTOIONIZATION; SECONDARY ION MASS SPECTROMETRY; SELF ASSEMBLED MONOLAYERS; SILICON; SILICON WAFERS; SPECTROMETRY; SURFACE TREATMENT; X RAY PHOTOELECTRON SPECTROSCOPY;

CROSSLINKED STRUCTURES; CROSSLINKING REACTION; DIELS-ALDER REACTION; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; INFRARED REFLECTION ABSORPTION SPECTROSCOPY; PHOTOCHEMICAL CROSS-LINKING; PHOTOINDUCED REACTION; TIME OF FLIGHT SECONDARY ION MASS SPECTROMETRY;

CROSSLINKING;

ACETAMIDE; ACETAMIDE DERIVATIVE; CARBOXYLIC ACID; NANOMATERIAL; SILICON;

CHEMISTRY; NANOTECHNOLOGY; PHOTOCHEMISTRY; PROCEDURES; SURFACE PROPERTY;

ACETAMIDES; CARBOXYLIC ACIDS; NANOSTRUCTURES; NANOTECHNOLOGY; PHOTOCHEMICAL PROCESSES; SILICON; SURFACE PROPERTIES;

EID: 84925002890     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la505011j     Document Type: Article

References (59)

1. Okamura, Y.; Kabata, K.; Kinoshita, M.; Saitoh, D.; Takeoka, S. Free-Standing Biodegradable Poly(lactic acid) Nanosheet for Sealing Operations in Surgery Adv. Mater. 2009, 21, 4388-4392
2. Tang, Z.; Kotov, N. A.; Magnov, S.; Ozturk, B. Nanostructured artificial nacre Nat. Mater. 2003, 2, 413-418
3. Mallwitz, F.; Laschewsky, A. Direct Access to Stable, Freestanding Polymer Membranes by Layer-by-Layer Assembly of Polyelectrolytes Adv. Mater. 2005, 17, 1296-1299
4. Mamedov, A.; Kotov, N. A. Free-Standing Layer-by-Layer Assembled Films of Magnetite Nanoparticles Langmuir 2000, 16, 5530-5533
5. Nardin, C.; Winterhalter, M.; Meier, W. Giant Free-Standing ABA Triblock Copolymer Membranes Langmuir 2000, 16, 7708-7712
6. Zheng, Y.; Zhou, H.; Liu, D.; Floudas, G.; Wagner, M.; Koynov, K.; Mezger, M.; Butt, H.-J.; Ikeda, T. Supramolecular Thiophene Nanosheets Angew. Chem., Int. Ed. 2013, 52, 4845-4848
7. Nam, K. T.; Shelby, S. A.; Choi, P. H.; Marciel, A. B.; Chen, R.; Tan, L.; Chu, T. K.; Mesch, R. A.; Lee, B.-C.; Connolly, M. D.; Kisielowski, C.; Zuckermann, R. N. Free-floating ultrathin two-dimensional crystals from sequence-specific peptoid polymers Nat. Mater. 2010, 9, 454-460
8. Matsui, J.; Mitsuishi, M.; Aoki, A.; Miyashita, T. Molecular Optical Gating Devices Based on Polymer Nanosheets Assemblies J. Am. Chem. Soc. 2004, 126, 3708-3709
9. Eck, W.; Küller, A.; Grunze, M.; Völlkel, B.; Gölzhäuser, A. Freestanding Nanosheets from Crosslinked Biphenyl Self-Assembled Monolayers Adv. Mater. 2005, 17, 2583-2587
10. Beyer, A.; Godt, A.; Amin, I.; Nottbohm, C. T.; Schmidt, C.; Zhao, J.; Gölzhäuser, A. Fully cross-linked and chemically patterned self-assembled monolayers Phys. Chem. Chem. Phys. 2008, 10, 7233-7238
11. Nottbohm, C. T.; Wiegmann, S.; Beyer, A.; Gölzhäuser, A. Holey nanosheets by patterning with UV/ozone Phys. Chem. Chem. Phys. 2010, 17, 4324-4328
12. Amin, I.; Steenackers, M.; Zhang, N.; Schubel, R.; Beyer, A.; Gölzhäuser, A.; Jordan, R. Patterned Polymer Carpets Small 2011, 7, 683-687
13. Turchanin, A.; Weber, D.; Büenfeld, M.; Kisielowski, C.; Fistul, M.; Efetov, K. B.; Weimann, T.; Stosch, R.; Mayer, J.; Gölzhäuser, A. Conversion of Self-Assembled Monolayers into Nanocrystalline Graphene: Structure and Electric Transport ACS Nano 2011, 5, 3896-3904
14. Vendamme, R.; Onoue, S. Y.; Nakao, A.; Kunitake, T. Robust free-standing nanomembranes of organic/inorganic interpenetrating networks Nat. Mater. 2006, 5, 494-501
15. Guo, S.; Dong, S. Graphene nanosheet: synthesis, molecular engineering, thin film, hybrids, and energy and analytical applications Chem. Soc. Rev. 2011, 40, 2644-2672
16. Geim, A. K. Graphene: Status and Prospects Science 2009, 324, 1530-1534
17. Coleman, J. N.; Lotya, M.; O'Neill, A.; Bergin, S. D.; King, P. J.; Khan, U.; Young, K.; Gaucher, A.; De, S.; Smith, R. J.; Shvets, I. V.; Arora, S. K.; Stanton, G.; Kim, H.-Y.; Lee, K.; Kim, G. T.; Duesberg, G. S.; Hallam, T.; Boland, J. J.; Wang, J. J.; Donegan, J. F.; Grunlan, J. C.; Moriarty, G.; Shmeliov, A.; Nicholls, R. J.; Perkins, J. M.; Grieveson, E. M.; Theuwissen, K.; McComb, D. W.; Nellist, P. D.; Nicolosi, V. Two-Dimensional Nanosheets Produced by Liquid Exfoliation of Layered Materials Science 2011, 331, 568-571
18. Osada, M.; Sasaki, T. Two-Dimensional Dielectric Nanosheets: Novel Nanoelectronics From Nanocrystal Building Blocks Adv. Mater. 2012, 24, 210-228
19. Wang, X.; Zhi, L. J.; Müllen, K. Transparent, Conductive Graphene Electrodes for Dye-Sensitized Solar Cells Nano Lett. 2008, 8, 323-327
20. Schnietz, M.; Turchanin, A.; Nottbohm, C. T.; Beyer, A.; Solak, H. H.; Hinze, P.; Weimann, T.; Gölzhäuser, A. Chemically Functionalized Carbon Nanosieves with 1-nm Thickness Small 2009, 5, 2651-2655
21. Garaj, S.; Hubbard, W.; Reina, A.; Kong, J.; Branton, D.; Golovchenko, J. A. Graphene as a subnanometre trans-electrode membrane Nature 2010, 467, 190-193
22. Robinson, J. T.; Zalalutdinov, M.; Baldwin, J. W.; Snow, E. S.; Wei, Z. Q.; Sheehan, P.; Houston, B. H. Wafer-scale Reduced Graphene Oxide Films for Nanomechanical Devices Nano Lett. 2008, 8, 3441-3445
23. Nottbohm, C. T.; Beyer, A.; Sologubenko, A. S.; Ennen, I.; Hütten, A.; Rösner, H.; Eck, W.; Mayer, J.; Gölzhäuser, A. Novel carbon nanosheets as support for ultrahigh-resolution structural analysis of nanoparticles Ultramicroscopy 2008, 108, 885-892
24. Meyer, J. C.; Girit, C. O.; Crommie, M. F.; Zettl, A. Imaging and dynamics of light atoms and molecules on graphene Nature 2008, 454, 319-322
25. Stankovich, S.; Dikin, D. A.; Dommett, G. H. B.; Kohlhaas, K. M.; Zimney, E. J.; Stach, E. A.; Piner, R. D.; Nguyen, S. T.; Ruoff, R. S. Graphene-based composite materials Nature 2006, 442, 282-286
26. Eda, G.; Chhowalla, M. Graphene-based Composite Thin Films for Electronics Nano Lett. 2009, 9, 814-818
27. Sakamoto, J.; van Heijst, J.; Lukin, O.; Schlüter, A. D. Two-Dimensional Polymers: Just a Dream of Synthetic Chemists? Angew. Chem., Int. Ed. 2009, 48, 1030-1069
28. Colson, J. W.; Dichtel, W. R. Rationally synthesized two-dimensional polymers Nat. Chem. 2013, 5, 453-465
29. Chen, Y.; Li, M.; Payamyar, P.; Zheng, Z.; Sakamoto, J.; Schlüter, A. D. Room Temperature Synthesis of a Covalent Monolayer Sheet at Air/Water Interface Using a Shape-Persistent Photoreactive Amphiphilic Monomer ACS Macro Lett. 2014, 3, 153-158
30. Kissel, P.; Erni, R.; Schweizer, W. B.; Rossell, M. D.; King, B. T.; Bauer, T.; Götzinger, S.; Schlüter, A. D.; Sakamoto, J. A two-dimensional polymer prepared by organic synthesis Nat. Chem. 2012, 4, 287-291
31. Bhola, R.; Payamyar, P.; Murray, D. J.; Kumar, B.; Teator, A. J.; Schmidt, M. U.; Hammer, S. M.; Saha, A.; Sakamoto, J.; Schlüter, A. D.; King, B. T. A Two-Dimensional Polymer from the Anthracene Dimer and Triptycene Motifs J. Am. Chem. Soc. 2013, 135, 14134-14141
32. Bieri, M.; Treier, M.; Cai, J.; Aït-Mansour, K.; Ruffieux, P.; Gröning, O.; Gröning, P.; Kastler, M.; Rieger, R.; Feng, X.; Müllen, K.; Fasel, R. Porous graphenes: two-dimensional polymer synthesis with atomic precision Chem. Commun. 2009, 6919-6921
33. Bieri, M.; Nguyen, M.-T.; Gröning, O.; Cai, J.; Treier, M.; Aït-Mansour, K.; Ruffieux, P.; Pignedoli, C. A.; Passerone, D.; Kastler, M.; Müllen, K.; Fasel, R. Two-Dimensional Polymer Formation on Surfaces: Insight into the Roles of Precursor Mobility and Reactivity J. Am. Chem. Soc. 2010, 132, 16669-16676
34. Bieri, M.; Blankenburg, S.; Kivala, M.; Pignedoli, C. A.; Ruffieux, P.; Müllen, K.; Fasel, R. Surface-supported 2D heterotriangulene polymers Chem. Commun. 2011, 47, 10239-10241
35. Orski, S. V.; Poloukhtine, A. A.; Arumugam, S.; Mao, L.; Popik, V. V.; Locklin, J. High Density Orthogonal Surface Immobilization via Photoactivated Copper-Free Click Chemistry J. Am. Chem. Soc. 2010, 132, 11024-11026
36. McNitt, C. D.; Popik, V. V. Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations Org. Biomol. Chem. 2012, 10, 8200-8202
37. Song, W.; Wang, Y.; Qu, J.; Madden, M. M.; Lin, Q. A Photoinducible 1,3-Dipolar Cycloaddition Reaction for Rapid, Selective Modification of Tetrazole-Containing Proteins Angew. Chem., Int. Ed. 2008, 47, 2832-2835
38. Wang, Y.; Song, W.; Hu, W. J.; Lin, Q. Fast alkene functionalization in vivo by Photoclick chemistry: HOMO lifting of nitrile imine dipoles Angew. Chem., Int. Ed. 2009, 48, 5330-5333
39. Pauloehrl, T.; Delaittre, G.; Bruns, M.; Meiβler, M.; Börner, H. G.; Bastmeyer, M.; Barner-Kowollik, C. Bio)Molecular Surface Patterning by Phototriggered Oxime Ligation Angew. Chem., Int. Ed. 2012, 51, 9181-9184
40. Arumugam, S.; Orski, S. V.; Popik, V. V. Photoreactive Polymer Brushes for High-Density Patterned Surface Derivatization Using a Diels-Alder Photoclick Reaction J. Am. Chem. Soc. 2012, 134, 179-182
41. Arumugam, S.; Popik, V. V. Attach, remove, or replace: reversible surface functionalization using thiol-quinone methide photoclick chemistry J. Am. Chem. Soc. 2012, 134, 8408-8411
42. Pauloehrl, T.; Delaittre, G.; Winkler, V.; Welle, A.; Bruns, M.; Börner, H. G.; Greiner, A. M.; Bastmeyer, M.; Barner-Kowollik, C. Adding Spatial Control to Click Chemistry: Phototriggered Diels-Alder Surface (Bio)functionalization at Ambient Temperature Angew. Chem., Int. Ed. 2012, 51, 1071-1074
43. Glassner, M.; Oehlenschlaeger, K. K.; Welle, A.; Bruns, M.; Barner-Kowollik, C. Polymer surface patterning via Diels-Alder trapping of photo-generated thioaldehydes Chem. Commun. 2013, 49, 633-635
44. Pauloehrl, T.; Welle, A.; Oehlenschlaeger, K. K.; Barner-Kowollik, C. Spatially controlled surface immobilization of nucleophiles via trapping of photo-generated thioaldehydes Chem. Sci. 2013, 4, 3503-3507
45. Wathier, M.; Polidori, A.; Ruiz, K.; Fabiano, A.-S.; Pucci, B. Stabilization of polymerized vesicular systems: an application of the dynamic molecular shape concept Chem. Phys. Lipids 2002, 115, 17-37
46. Liu, D.; Chen, W.; Sun, K.; Deng, K.; Zhang, W.; Wang, Z.; Jiang, X. Resettable, Multi-Readout Logic Gates Based on Controllably Reversible Aggregation of Gold Nanoparticles Angew. Chem., Int. Ed. 2011, 50, 4103-4107
47. Vedejs, E.; Eberlein, T. H.; Wilde, R. G. Internal thioaldehyde trapping by enes and dienes J. Org. Chem. 1988, 53, 2220-2226
48. Kunishima, M.; Kawachi, C.; Iwasaki, F.; Terao, K.; Tani, S. Synthesis and characterization of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride Tetrahedron Lett. 1999, 40, 5327-5330
49. Quick, A. S.; Rothfuss, H.; Welle, A.; Richter, B.; Fischer, J.; Wegener, M.; Barner-Kowollik, C. Fabrication and Spatially Resolved Functionalization of 3D Microstructures via Multiphoton-Induced Diels-Alder Chemistry Adv. Funct. Mater. 2014, 24, 3571-3580
50. Huang, C.; Moosmann, M.; Jin, J.; Heiler, T.; Walheim, S.; Schimmel, T. Polymer blend lithography: A versatile method to fabricate nanopatterned self-assembled monolayers Beilstein J. Nanotechnol. 2012, 3, 620-628
51. Parry, K. L.; Shard, A. G.; Short, R. D.; White, R. G.; Whittle, J. D.; Wright, A. ARXPS characterisation of plasma polymerised surface chemical gradients Surf. Interface Anal. 2006, 38, 1497-1504
52. Scofield, J. H. Hartree-Slater subshell photoionization cross-sections at 1254 and 1487 eV J. Electron Spectrosc. Relat. Phenom. 1976, 8, 129-137
53. Tanuma, S.; Powell, C. J.; Penn, D. R. Calculations of electron inelastic mean free paths. V. Data for 14 organic compounds over the 50-2000 eV range Surf. Interface Anal. 1994, 21, 165-176
54. Sherman, R.; Hirt, D.; Vane, R. Surface cleaning with the carbon dioxide snow jet J. Vac. Sci. Technol., A 1994, 12, 1876-1881
55. Wagner, P. J.; Lindstrom, M. J. Intramolecular charge-transfer interactions in triplet keto sulfides J. Am. Chem. Soc. 1987, 109, 3062-3067
56. Duchenet, V.; Vallée, Y. The reaction of thiols with electron-deficient thioaldehydes. A new synthesis of unsymmetrical disulfides J. Chem. Soc., Chem. Commun. 1993, 806-807
57. Preuss, C. M.; Zieger, M.; Rodriguez-Emmenegger, C.; Zydziak, N.; Trouillet, V.; Goldmann, A. S.; Barner-Kowollik, C. Fusing Catechol-Driven Surface Anchoring with Rapid Hetero Diels-Alder Ligation ACS Macro Lett. 2014, 3, 1169-1173
58. Cossement, D.; Gouttebaron, R.; Cornet, V.; Viville, P.; Hecq, M.; Lazzaroni, R. PLA-PMMA blends: A study by XPS and ToF-SIMS Appl. Surf. Chem. 2006, 252, 6636-6639
59. Kattner, J.; Hoffmann, H. In Handbook of Vibrational Spectroscopy; Chalmers, J. M.; Griffiths, P. R., Eds.; John Wiley & Sons Ltd: Chichester, U.K., 2002; p 20.