Thermodynamic control of 2d bicomponent porous networks of melamine and melem: Diverse hydrogen-bonded networks

Journal of Physical Chemistry C

Volumn 117, Issue 47, 2013, Pages 24815-24821

  Uemura, Shinobu ^a,c   Aono, Masashi ^a   Sakata, Kenki ^a   Komatsu, Tamikuni ^b   Kunitake, Masashi ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b HIGH ENERGY ACCELERATOR RESEARCH ORGANIZATION KEK   (Japan)

^c KAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMICAL POTENTIAL; HYDROGEN BONDED NETWORK; IN-SITU SCANNING TUNNELING MICROSCOPIES; SELF ASSEMBLED STRUCTURES; SOLUTION CONCENTRATION; STRUCTURAL PHASE TRANSITION; SURFACE CONCENTRATION; THERMODYNAMIC CONTROL;

HYDROGEN BONDS; SCANNING TUNNELING MICROSCOPY;

HONEYCOMB STRUCTURES;

EID: 84889569285     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp406810c     Document Type: Article

References (62)

1. Cicoira, F.; Santato, C.; Rosei, F. Two-Dimensional Nanotemplates as Surface Cues for the Controlled Assembly of Organic Molecules Top. Curr. Chem. 2008, 285, 203-267
2. Elemans, J. A. A. W.; Lei, S.; De Feyter, S. Molecular and Supramolecular Networks on Surfaces: From Two-Dimensional Crystal Engineering to Reactivity Angew. Chem., Int. Ed. 2009, 48, 7298-7333
3. Lackinger, M.; Heckl, W. M. Carboxylic Acids: Versatile Building Blocks and Mediators for Two-Dimensional Supramolecular Self-Assembly Langmuir 2009, 25, 11307-11321
4. Bonifazi, D.; Mohnani, S.; Llanes-Pallas, A. Supramolecular Chemistry at Interfaces: Molecular Recognition on Nanopatterned Porous Surfaces Chem.-Eur. J. 2009, 15, 7004-7025
5. Phillips, A. G.; Beton, P. H.; Champness, N. R. Two-Dimensional Supramolecular Chemistry on Surfaces Chem. Sci. 2011, 2, 1440-1448
6. Mali, K. S.; Adisoejoso, J.; Ghijsens, E.; De Cat, I.; De Feyter, S. Exploring the Complexity of Supramolecular Interactions for Patterning at the Liquid-Solid Interface Acc. Chem. Res. 2012, 45, 1309-1320
7. Yoshimoto, S.; Honda, Y.; Ito, O.; Itaya, K. Supramolecular Pattern of Fullerene on 2D Bimolecular "Chessboard" Consisting of Bottom-up Assembly of Porphyrin and Phthalocyanine Molecules J. Am. Chem. Soc. 2008, 130, 1085-1092
8. Lei, S.; Tahara, K.; De Schryver, F. C.; Van der Auweraer, M.; Tobe, Y.; De Feyter, S. One Building Block, Two Different Supramolecular Surface-Confined Patterns: Concentration in Control at the Solid-Liquid Interface Angew. Chem., Int. Ed. 2008, 47, 2964-2968
9. Uemura, S.; Sengupta, S.; Würthner, F. Cyclic Self-Assembled Structures of Chlorophyll Dyes on HOPG by the Dendron Wedge Effect Angew. Chem., Int. Ed. 2009, 48, 7825-7828
10. Arrigoni, C.; Schull, G.; Bléger, D.; Douillard, L.; Fiorini-Debuisschert, C.; Mathevet, F.; Kreher, D.; Attias, A.-J.; Charra, F. Structure and Epitaxial Registry on Graphite of a Series of Nanoporous Self-Assembled Molecular Monolayers J. Phys. Chem. Lett. 2010, 1, 190-194
11. Rajwar, D.; Sun, X.; Cho, S.-J.; Grimsdale, A. C.; Fichou, D. Synthesis and 2D Self-Assembly at the Liquid-Solid Interface of End-Substituted Star-Shaped Oligophenylenes CrystEngComm 2012, 14, 5182-5187
12. Griessl, S.; Lackinger, M.; Edelwirth, M.; Hietschold, M.; Heckl, W. M. Self-Assembled Two-Dimensional Molecular Host-Guest Architectures From Trimesic Acid Single Mol. 2002, 3, 25-31
13. Theobald, J. A.; Oxtoby, N. S.; Phillips, M. A.; Champness, N. R.; Beton, P. H. Controlling Molecular Deposition and Layer Structure with Supramolecular Surface Assemblies Nature 2003, 424, 1029-1031
14. Xu, W.; Wang, J.-G.; Jacobsen, M. F.; Mura, M.; Yu, M.; Kelly, R. E. A.; Meng, Q.; Lægsgaard, E.; Stensgaard, I.; Linderoth, T. R.; Kjems, J.; Kantorovich, L. N.; Gothelf, K. V.; Besenbacher, F. Supramolecular Porous Network Formed by Molecular Recognition Between Chemically Modified Nucleobases Guanine and Cytosine Angew. Chem., Int. Ed. 2010, 49, 9373-9377
15. Liang, H.; Sun, W.; Jin, X.; Li, H.; Li, J.; Hu, X.; Teo, B. K.; Wu, K. Two-Dimensional Molecular Porous Networks Formed by Trimesic Acid and 4,4′-Bis(4-pyridyl)biphenyl on Au(111) Through Hierarchical Hydrogen Bonds: Structural Systematics and Control of Nanopore Size and Shape Angew. Chem., Int. Ed. 2011, 50, 7562-7566
16. Cañas-Ventura, M. E.; Xiao, W.; Wasserfallen, D.; Müllen, K.; Brune, H.; Barth, J. V.; Fasel, R. Self-Assembly of Periodic Bicomponent Wires and Ribbons Angew. Chem., Int. Ed. 2007, 46, 1814-1818
17. Hoeben, F. J. M.; Zhang, J.; Lee, C. C.; Pouderoijen, M. J.; Wolffs, M.; Würthner, F.; Schenning, A. P. H. J.; Meijer, E. W.; De Feyter, S. Visualization of Various Supramolecular Assemblies of Oligo(para- phenylenevinylene)-Melamine and Perylene Bisimide Chem.-Eur. J. 2008, 14, 8579-8589
18. Kampschulte, L.; Werblowsky, T. L.; Kishore, R. S.; Schmittel, M.; Heckl, W. M.; Lackinger, M. Thermodynamical Equilibrium of Binary Supramolecular Networks at the Liquid-Solid Interface J. Am. Chem. Soc. 2008, 130, 8502-8507
19. MacLeod, J. M.; Ivasenko, O.; Fu, C.; Taerum, T.; Rosei, F.; Perepichka, D. F. Supramolecular Ordering in Oligothiophene-Fullerene Monolayers J. Am. Chem. Soc. 2009, 131, 16844-16850
20. Ahn, S.; Matzger, A. J. Six Different Assemblies from One Building Block: Two-Dimensional Crystallization of an Amide Amphiphile J. Am. Chem. Soc. 2010, 132, 11364-11371
21. Ciesielski, A.; Cadeddu, A.; Palma, C.-A.; Gorczyński, A.; Patroniak, V.; Cecchini, M.; Samorì, P. Self-Templating 2D Supramolecular Networks: A New Avenue to Reach Control over a Bilayer Formation Nanoscale 2011, 3, 4125-4129
22. Silly, F. Two-Dimensional 1,3,5-Tris(4-carboxyphenyl)benzene Self-Assembly at the 1-Phenyloctane/Graphite Interface Revisited J. Phys. Chem. C 2012, 116, 10029-10032
23. Zhou, H.; Maris, T.; Wuest, J. D. Using Systematic Comparisons of 2D and 3D Structures To Reveal Principles of Molecular Organization. Tetraesters of Linear Bisisophthalic Acids J. Phys. Chem. C 2012, 116, 13052-13062
24. Fu, C.; Rosei, F.; Perepichka, D. F. 2D Self-Assembly of Fused Oligothiophenes: Molecular Control of Morphology ACS Nano 2012, 6, 7973-7980
25. Ishikawa, Y.; Ohira, A.; Sakata, M.; Hirayama, C.; Kunitake, M. A Two-Dimensional Molecular Network Structure of Trimesic Acid Prepared by Adsorption-Induced Self-Organization Chem. Commun. 2002, 2652-2653
26. Yuan, Q.; Xing, Y.; Borguet, E. Optimizing Single-Molecule Conductivity of Conjugated Organic Oligomers with Carbodithioate Linkers J. Am. Chem. Soc. 2010, 132, 5054-5060
27. Lin, N.; Stepanow, S.; Ruben, M.; Barth, J. V. Surface-Confined Supramolecular Coordination Chemistry Top. Curr. Chem. 2009, 287, 1-44
28. Kley, C. S.; Cechal, J.; Kumagai, T.; Schramm, F.; Ruben, M.; Stepanow, S.; Kern, K. Highly Adaptable Two-Dimensional Metal-Organic Coordination Networks on Metal Surfaces J. Am. Chem. Soc. 2012, 134, 6072-6075
29. Li, Y.; Xiao, J.; Shubina, T. E.; Chen, M.; Shi, Z.; Schmid, M.; Steinrück, H.-P.; Gottfried, J. M.; Lin, N. Coordination and Metalation Bifunctionality of Cu with 5,10,15,20-tetra(4-pyridyl)porphyrin: Toward a Mixed-Valence Two-Dimensional Coordination Network J. Am. Chem. Soc. 2012, 134, 6401-6408
30. Grill, L.; Dyer, M.; Lafferentz, L.; Persson, M.; Peters, M. V.; Hecht, S. Nano-Architectures by Covalent Assembly of Molecular Building Blocks Nat. Nanotechnol. 2007, 2, 687-691
31. Zwaneveld, N. A. A.; Pawlak, R.; Abel, M.; Catalin, D.; Gigmes, D.; Bertin, D.; Porte, L. Organized Formation of 2D Extended Covalent Organic Frameworks at Surfaces J. Am. Chem. Soc. 2008, 130, 6678-6679
32. Weigelt, S.; Busse, C.; Bombis, C.; Knudsen, M. M.; Gothelf, K. V.; Lægsgaard, E.; Besenbacher, F.; Linderoth, T. R. Surface Synthesis of 2D Branched Polymer Nanostructures Angew. Chem., Int. Ed. 2008, 47, 4406-4410
33. Guntzler, R.; Walch, H.; Eder, G.; Kloft, S.; Heckl, W. M.; Lackinger, M. Surface Mediated Synthesis of 2D Covalent Organic Frameworks: 1,3,5-tris(4-bromophenyl)benzene on Graphite(001), Cu(111), and Ag(110) Chem. Commun. 2009, 4456-4458
34. Tanoue, R.; Higuchi, R.; Enoki, N.; Miyasato, Y.; Uemura, S.; Kimizuka, N.; Stieg, A. Z.; Gimzewski, J. K.; Kunitake, M. Thermodynamically Controlled Self-Assembly of Covalent Nanoarchitectures in Aqueous Solution ACS Nano 2011, 5, 3923-3929
35. Guan, C.-Z.; Wang, D.; Wan, L.-J. Construction and Repair of Highly Ordered 2D Covalent Networks by Chemical Equilibrium Regulation Chem. Commun. 2012, 48, 2643-2945
36. Gutzler, R.; Sirtl, T.; Dienstmaier, J. F.; Mahata, K.; Heckl, W. M.; Schmittel, M.; Lackinger, M. Reversible Phase Transitions in Self-Assembled Monolayers at the Liquid-Solid Interface: Temperature-Controlled Opening and Closing of Nanopores J. Am. Chem. Soc. 2010, 132, 5084-5090
37. Silly, F.; Shaw, A. Q.; Castell, M. R.; Briggs, G. A. D.; Mura, M.; Martsinovich, N.; Kantorovich, L. Melamine Structures on the Au(111) Surface J. Phys. Chem. C 2008, 112, 11476-11480
38. Zhang, H.-M.; Xie, Z.-X.; Long, L.-S.; Zhong, H.-P.; Zhao, W.; Mao, B.-W.; Xu, X.; Zheng, L.-S. One-Step Preparation of Large-Scale Self-Assembled Monolayers of Cyanuric Acid and Melamine Supramolecular Species on Au(111) Surfaces J. Phys. Chem. C 2008, 112, 4209-4218
39. Zhang, X.; Chen, T.; Chen, Q.; Wang, L.; Wan, L.-J. Self-Assembly and Aggregation of Melamine and Melamine-Uric/Cyanuric Acid Investigated by STM and AFM on Solid Surfaces Phys. Chem. Chem. Phys. 2009, 11, 7708-7712
40. Mura, M.; Silly, F.; Burlakov, V.; Castell, M.; Briggs, G.; Kantorovich, L. Formation Mechanism for a Hybrid Supramolecular Network Involving Cooperative Interactions Phys. Rev. Lett. 2012, 108, 176103
41. Staniec, P. A.; Perdigao, L. M. A.; Rogers, B. L.; Champness, N. R.; Beton, P. H. Honeycomb Networks and Chiral Superstructures Formed by Cyanuric Acid and Melamine on Au(111) J. Phys. Chem. C 2007, 111, 886-893
42. Xu, W.; Dong, M.; Gersen, H.; Rauls, E.; Vázquez-Campos, S.; Crego-Calama, M.; Reinhoudt, D. N.; Stensgaard, I.; Laegsgaard, E.; Linderoth, T. R.; Besenbacher, F. Cyanuric Acid and Melamine on Au(111): Structure and Energetics of Hydrogen-Bonded Networks Small 2007, 3, 854-858
43. Palma, C.-A.; Bjork, J.; Bonini, M.; Dyer, M. S.; Llanes-Pallas, A.; Bonifazi, D.; Persson, M.; Samorì, P. Tailoring Bicomponent Supramolecular Nanoporous Networks: Phase Segregation, Polymorphism, and Glasses at the Solid-Liquid Interface J. Am. Chem. Soc. 2009, 131, 13062-13071
44. Gardener, J. A.; Shvarova, O. Y.; Briggs, G. A. D.; Castell, M. R. Intricate Hydrogen-Bonded Networks: Binary and Ternary Combinations of Uracil, PTCDI, and Melamine J. Phys. Chem. C 2010, 114, 5859-5866
45. 3+ Nanoscale 2012, 4, 148-151
46. González-Rodríguez, D.; Schenning, A. P. H. J. Hydrogen-Bonded Supramolecular π-Functional Materials Chem. Mater. 2011, 23, 310-325
47. Madueno, R.; Räisänen, M. T.; Silien, C.; Buck, M. Functionalizing Hydrogen-Bonded Surface Networks with Self-Assembled Monolayers Nature 2008, 454, 618-621
48. Franklin, E. C. The Ammono Carbonic Acids J. Am. Chem. Soc. 1922, 44, 486-507
49. Komatsu, T. Prototype Carbon Nitrides Similar to the Symmetric Triangular Form of Melon J. Mater. Chem. 2001, 11, 802-805
50. Miller, D. R.; Swenson, D. C.; Gillan, E. G. Synthesis and Structure of 2,5,8-Triazido- s -Heptazine: An Energetic and Luminescent Precursor to Nitrogen-Rich Carbon Nitrides J. Am. Chem. Soc. 2004, 126, 5372-5373
51. Kroke, E.; Schwarz, M. Novel Group 14 Nitrides Coord. Chem. Rev. 2004, 248, 493-532
52. Schwarzer, A.; Saplinova, T.; Kroke, E. Tri-s-triazines (s-Heptazines)-From a "Mystery Molecule" to Industrially Relevant Carbon Nitride Materials Coord. Chem. Rev. 2013, 257, 2032-2062
53. Wang, X.; Maeda, K.; Thomas, A.; Takanabe, K.; Xin, G.; Carlsson, J. M.; Domen, K.; Antonietti, M. A Metal-Free Polymeric Photocatalyst for Hydrogen Production from Water under Visible Light Nat. Mater. 2009, 8, 76-80
54. Komatsu, T. The First Synthesis and Characterization of Cyameluric High Polymers Macromol. Chem. Phys. 2001, 202, 19-25
55. Makowski, S. J.; Köstler, P.; Schnick, W. Formation of a Hydrogen-Bonded Heptazine Framework by Self-Assembly of Melem into a Hexagonal Channel Structure Chem.-Eur. J. 2012, 18, 3248-3257
56. 3-New Targets and Prospects Chem.-Eur. J. 2012, 18, 12052-12058
57. Ishii, A.; Habu, K.; Kishi, S.; Ohtsu, H.; Komatsu, T.; Osaka, K.; Kato, K.; Kimura, S.; Takata, M.; Hasegawa, M.; Shigesato, Y. Novel Emission Properties of Melem Caused by the Heavy Metal Effect of Lanthanides(III) in a LB Film Photochem. Photobiol. Sci. 2007, 6, 804-809
58. Uemura, S.; Aono, M.; Komatsu, T.; Kunitake, M. Two-Dimensional Self-Assembled Structures of Melamine and Melem at the Aqueous Solution-Au(111) Interface Langmuir 2011, 27, 1336-1340
59. Eichhorn, J.; Schlögl, S.; Lotsch, B. V.; Schnick, W.; Heckl, W. M.; Lackinger, M. Self-Assembly of Melem on Ag(111)-Emergence of Porous Structures Based on Amino-Heptazine Hydrogen Bonds CrystEngComm 2011, 13, 5559-5565
60. Finkel'shtein, A. I.; Spiridonova, N. V. Chemical Properties and Molecular Structure of Derivatives of sym -Heptazine [1,3,4,6,7,9,9b- Heptaazaphenalene, tri-1,3,5-triazine]. Russ Chem. Rev. 1964, 33, 400-405
61. Uemura, S.; Tanoue, R.; Yilmaz, N.; Ohira, A.; Kunitake, M. Molecular Dynamics in Two-Dimensional Supramolecular Systems Observed by STM Materials 2010, 3, 4252-4276
62. Dai, P.-X.; Chen, T.; Wang, D.; Wan, L.-J. Potential Dependent Adsorption Geometry of 2,5-Dihydroxybenzoic Acid on a Au(111) Surface: An in Situ Electrochemical Scanning Tunneling Microscopy Study J. Phys. Chem. C 2012, 116, 6208-6214