Selecting two-dimensional halogen-halogen bonded self-assembled 1,3,5-tris(4-iodophenyl)benzene porous nanoarchitectures at the solid-liquid interface

Journal of Physical Chemistry C

Volumn 117, Issue 39, 2013, Pages 20244-20249

  Silly, Fabien ^a  

^a CNRS UMR 3299   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE MOLECULES; DIFFERENT SOLVENTS; GRAPHITE SURFACES; MOLECULAR DIMERS; NANOARCHITECTURES; ORGANIC NETWORKS; POROUS STRUCTURES; SOLID-LIQUID INTERFACES;

BENZENE; DIMERS; HYDROGEN BONDS; IODINE; MOLECULES; SCANNING TUNNELING MICROSCOPY;

TWO DIMENSIONAL;

EID: 84885158152     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp4057626     Document Type: Article

References (59)

1. Pawin, G.; Wong, K. L.; Kwon, K. Y.; Bartels, L. A Homomolecular Porous Network at a Cu(111) Surface Science 2006, 313, 961
2. Lobo-Checa, J.; Matena, M.; Muller, K.; Dil, J. H.; Meier, F.; Gade, L. H.; Jung, T. A.; Stohr, M. Band Formation from Coupled Quantum Dots Formed by a Nanoporous Network on a Copper Surface Science 2009, 325, 300-303
3. Klappenberger, F.; Kühne, D.; Krenner, W.; Silanes, I.; Arnau, A.; Garcia de Abajo, F. J.; Klyatskaya, S.; Ruben, M.; Barth, J. V. Tunable Quantum Dot Arrays Formed from Self-Assembled Metal-Organic Networks Phys. Rev. Lett. 2011, 106, 026802
4. Barth, J. V.; Costantini, G.; Kern, K. Engineering Atomic and Molecular Nanostructures at Surfaces Nature 2005, 437, 671-679
5. Chen, T.; Chen, Q.; Zhang, X.; Wang, D.; Wan, L.-J. Chiral Kagome Network from Thiacalix[4]arene Tetrasulfonate at the Interface of Aqueous Solution/Au(111) Surface: An in Situ Electrochemical Scanning Tunneling Microscopy Study J. Am. Chem. Soc. 2010, 132, 5598-5599
6. 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
7. Klyatskaya, S.; Klappenberger, F.; Schlickum, U.; Kühne, D.; Marschall, M.; Reichert, J.; Decker, R.; Krenner, W.; Zoppellaro, G.; Brune, H. Surface-Confined Self-Assembly of Di-Carbonitrile Polyphenyls Adv. Funct. Mater. 2011, 21, 1230-1240
8. Yang, Y.; Wang, C. Hierarchical Construction of Self-Assembled Low-Dimensional Molecular Architectures Observed by Using Scanning Tunneling Microscopy Chem. Soc. Rev. 2009, 38, 2576
9. Stepanow, S.; Lin, N.; Payer, D.; Schlickum, U.; Klappenberger, F.; Zoppellaro, G.; Ruben, M.; Brune, H.; Barth, J.; Kern, K. Surface-Assisted Assembly of 2D Metal-Organic Networks That Exhibit Unusual Threefold Coordination Symmetry Angew. Chem., Int. Ed. 2007, 46, 710-713
10. Liang, H.; He, Y.; Ye, Y.; Xu, X.; Cheng, F.; Sun, W.; Shao, X.; Wang, Y.; Li, J.; Wu, K. Two-Dimensional Molecular Porous Networks Constructed by Surface Assembling Coord. Chem. Rev. 2009, 253, 2959-2979
11. Gutzler, R.; Cardenas, L.; Rosei, F. Kinetics and Thermodynamics in Surface-Confined Molecular Self-Assembly Chem. Sci. 2011, 2, 2290-2300
12. Silien, C.; Räisänen, M. T.; Buck, M. A Supramolecular Network as Sacrificial Mask for the Generation of a Nanopatterned Binary Self-Assembled Monolayer Small 2010, 6, 391-394
13. Barth, J. V. Molecular Architectonic on Metal Surfaces Annu. Rev. Phys. Chem. 2007, 58, 375-407
14. Mura, M.; Silly, F.; Briggs, G. A. D.; Castell, M. R.; Kantorovich, L. N. H-Bonding Supramolecular Assemblies of PTCDI Molecules on the Au(111) Surface J. Phys. Chem. C 2009, 113, 21840-21848
15. Tanioku, C.; Matsukawa, K.; Matsumoto, A. Thermochromism and Structural Change in Polydiacetylenes Including Carboxy and 4-Carboxyphenyl Groups as the Intermolecular Hydrogen Bond Linkages in the Side Chain ACS Appl. Mater. Interfaces 2013, 5, 940-948
16. Priimagi, A.; Lindfors, K.; Kaivola, M.; Rochon, P. Efficient Surface-Relief Gratings in Hydrogen-Bonded Polymer-Azobenzene Complexes ACS Appl. Mater. Interfaces 2009, 1, 1183-1189
17. Hieulle, J.; Silly, F. Localized Intermolecular Electronic Coupling in Two-Dimensional Self-Assembled 3,4,9,10-Perylenetetracarboxylic Diimide Nanoarchitectures J. Mater. Chem. C 2013, 1, 4536-4539
18. Baris, B.; Luzet, V.; Duverger, E.; Sonnet, P.; Palmino, F.; Chérioux, F. Robust and Open Tailored Supramolecular Networks Controlled by the Template Effect of a Silicon Surface Angew. Chem., Int. Ed. 2011, 50, 4094-4098
19. 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
20. Shen, C.; Cebula, I.; Brown, C.; Zhao, J.; Zharnikov, M.; Buck, M. Structure of Isophthalic Acid Based Monolayers and Its Relation to the Initial Stages of Growth of Metal-Organic Coordination Layers Chem. Sci. 2012, 3, 1858-1865
21. Temirov, R.; Soubatch, S.; Neucheva, O.; Lassise, A. C.; Tautz, F. S. A Novel Method Achieving Ultra-High Geometrical Resolution in Scanning Tunnelling Microscopy New J. Phys. 2008, 10, 053012
22. Chen, T.; Yang, W.-H.; Wang, D.; Wan, L.-J. Globally Homochiral Assembly of Two-Dimensional Molecular Networks Triggered by Co-Absorbers Nat. Commun. 2013, 4, 1389
23. Silly, F.; Shaw, A. Q.; Briggs, G. A. D.; Castell, M. R. Epitaxial Ordering of a Perylenetetracarboxylic Diimide-Melamine Supramolecular Network Driven by the Au(111)-(22 × √3) Reconstruction Appl. Phys. Lett. 2008, 92, 023102
24. 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
25. Sun, X.; Jonkman, H. T.; Silly, F. Tailoring Two-Dimensional PTCDA-Melamine Self-Assembled Architectures at Room Temperature by Tuning Molecular Ratio Nanotechnology 2010, 21, 165602
26. Räisänen, M. T.; Slater, A. G.; Champness, N. R.; Buck, M. Effects of Pore Modification on the Templating of Guest Molecules in a 2D Honeycomb Network Chem. Sci. 2011, 3, 84-92
27. Ruben, M.; Payer, D.; Landa, A.; Comisso, A.; Gattinoni, C.; Lin, N.; Collin, J.; Sauvage, J.; De Vita, A.; Kern, K. 2D Supramolecular Assemblies of Benzene-1,3,5-triyl-tribenzoic Acid: Temperature-Induced Phase Transformations and Hierarchical Organization with Macrocyclic Molecules J. Am. Chem. Soc. 2006, 128, 15644-15651
28. Kampschulte, L.; Lackinger, M.; Maier, A.; Kishore, R. S. K.; Griessl, S.; Schmittel, M.; Heckl, W. M. Solvent Induced Polymorphism in Supramolecular 1,3,5-Benzenetribenzoic Acid Monolayers J. Phys. Chem. B 2006, 110, 10829-10836
29. 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
30. Xu, J.; Liu, X.; Ng, J. K.-P.; Lin, T.; He, C. Trimeric Supramolecular Liquid Crystals Induced by Halogen Bonds J. Mater. Chem. 2006, 16, 3540-3545
31. Gao, H. Y.; Shen, Q. J.; Zhao, X. R.; Yan, X. Q.; Pang, X.; Jin, W. J. Phosphorescent Co-Crystal Assembled by 1,4-Diiodotetrafluorobenzene with Carbazole Based on C-I...π Halogen Bonding J. Mater. Chem. 2012, 22, 5336-5343
32. Getmanenko, Y. A.; Fonari, M.; Risko, C.; Sandhu, B.; Galán, E.; Zhu, L.; Tongwa, P.; Hwang, D. K.; Singh, S.; Wang, H. Benzo[1,2-b:6,5-b′] dithiophene(dithiazole)-4,5-dione Derivatives: Synthesis, Electronic Properties, Crystal Packing and Charge Transport J. Mater. Chem. C 2013, 1, 1467-1481
33. Lafferentz, L.; Eberhardt, V.; Dri, C.; Africh, C.; Comelli, G.; Esch, F.; Hecht, S.; Grill, L. Controlling on-Surface Polymerization by Hierarchical and Substrate-Directed Growth Nat. Chem. 2012, 4, 215-220
34. Metrangolo, P.; Resnati, G.; Pilati, T.; Liantonio, R.; Meyer, F. Engineering Functional Materials by Halogen Bonding J. Polym. Sci., Polym. Chem. 2007, 45, 1-15
35. Meyer, F.; Dubois, P. Halogen Bonding at Work: Recent Applications in Synthetic Chemistry and Materials Science CrystEngComm 2013, 15, 3058-3071
36. Voth, A. R.; Khuu, P.; Oishi, K.; Ho, P. S. Halogen Bonds as Orthogonal Molecular Interactions to Hydrogen Bonds Nat. Chem. 2009, 1, 74-79
37. Lieberman, H. F.; Davey, R. J.; Newsham, D. M. T. Br...Br and Br...H Interactions in Action: Polymorphism, Hopping, and Twinning in 1,2,4,5-Tetrabromobenzene Chem. Mater. 2000, 12, 490-494
38. Gutzler, R.; Fu, C.; Dadvand, A.; Hua, Y.; MacLeod, J. M.; Rosei, F.; Perepichka, D. F. Halogen Bonds in 2D Supramolecular Self-Assembly of Organic Semiconductors Nanoscale 2012, 4, 5965-5971
39. DiLullo, A.; Chang, S.-H.; Baadji, N.; Clark, K.; Klöckner, J.-P.; Prosenc, M.-H.; Sanvito, S.; Wiesendanger, R.; Hoffmann, G.; Hla, S.-W. Molecular Kondo Chain Nano Lett. 2012, 12, 3174-3179
40. Walch, H.; Gutzler, R.; Sirtl, T.; Eder, G.; Lackinger, M. Material- and Orientation-Dependent Reactivity for Heterogeneously Catalyzed Carbon-Bromine Bond Homolysis J. Phys. Chem. C 2010, 114, 12604-12609
41. Meazza, L.; Foster, J. A.; Fucke, K.; Metrangolo, P.; Resnati, G.; Steed, J. W. Halogen-Bonding-Triggered Supramolecular Gel Formation Nat. Chem. 2013, 5, 42-47
42. Sun, A.; Lauher, J. W.; Goroff, N. S. Preparation of Poly(diiododiacetylene), an Ordered Conjugated Polymer of Carbon and Iodine Science 2006, 312, 1030-1034
43. Pigge, F. C.; Vangala, V. R.; Kapadia, P. P.; Swenson, D. C.; Rath, N. P. Hexagonal Crystalline Inclusion Complexes of 4-Iodophenoxy Trimesoate Chem. Commun. 2008, 4726-4728
44. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Mutual Induced Coordination in Halogen-Bonded Anionic Assemblies with (6,3) Cation-Templated Topologies Chem. Commun. 2008, 1635-1637
45. Troff, R. W.; Mäkelä, T.; Topić, F.; Valkonen, A.; Raatikainen, K.; Rissanen, K. Alternative Motifs for Halogen Bonding Eur. J. Org. Chem. 2013, 2013, 1617-1637
46. Eder, G.; Smith, E. F.; Cebula, I.; Heckl, W. M.; Beton, P. H.; Lackinger, M. Solution Preparation of Two-Dimensional Covalently Linked Networks by Polymerization of 1,3,5-Tri(4-iodophenyl)benzene on Au(111) ACS Nano 2013, 7, 3014-3021
47. Lee, S.-L.; Chu, Y.-C.; Wu, H.-J.; Chen, C.-h. Template-Assisted Assembly: Scanning Tunneling Microscopy Study of Solvent-Dependent Adlattices of Alkyl-Derivatized Tetrathiafulvalene Langmuir 2012, 28, 382-388
48. Shao, X.; Luo, X.; Hu, X.; Wu, K. Solvent Effect on Self-Assembled Structures of 3,8-Bis-hexadecyloxy-benzo[c]cinnoline on Highly Oriented Pyrolytic Graphite J. Phys. Chem. B 2005, 110, 1288-1293
49. Silly, F. A Robust Method for Processing Scanning Probe Microscopy Images and Determining Nanoobject Position and Dimensions J. Microsc. (Oxford, U. K.) 2009, 236, 211-218
50. Bui, T. T. T.; Dahaoui, S.; Lecomte, C.; Desiraju, G. R.; Espinosa, E. The Nature of Halogen...Halogen Interactions: A Model Derived from Experimental Charge-Density Analysis Angew. Chem., Int. Ed. 2009, 48, 3838-3841
51. Duarte, D. J.; Angelina, E. L.; Peruchena, N. M. On the Strength of the Halogen Bonds: Mutual Penetration, Atomic Quadrupole Moment and Laplacian Distribution of the Charge Density Analyses Comput. Theor. Chem. 2012, 998, 164-172
52. Zhang, X.; Zeng, Q.; Wang, C. Molecular Templates and Nano-Reactors: Two-Dimensional Hydrogen Bonded Supramolecular Networks on Solid/Liquid Interfaces RSC Adv. 2013, 3, 11351-11366
53. Silly, F.; Shaw, A. Q.; Porfyrakis, K.; Briggs, G. A. D.; Castell, M. R. Pairs and Heptamers of C70 Molecules Ordered via PTCDI-Melamine Supramolecular Networks Appl. Phys. Lett. 2007, 91, 253109
54. 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
55. Silly, F.; Shaw, A. Q.; Porfyrakis, K.; Warner, J. H.; Watt, A. A. R.; Castell, M. R.; Umemoto, H.; Akachi, T.; Shinohara, H.; Briggs, G. A. D. Grating of Single Lu@C82 Molecules Using Supramolecular Network Chem. Commun. 2008, 4616
56. Mura, M.; Silly, F.; Burlakov, V.; Castell, M. R.; Briggs, G. A. D.; Kantorovich, L. N. Formation Mechanism for a Hybrid Supramolecular Network Involving Cooperative Interactions Phys. Rev. Lett. 2012, 108, 176103
57. Pivetta, M.; Pacchioni, G. E.; Schlickum, U.; Barth, J. V.; Brune, H. Formation of Fe Cluster Superlattice in a Metal-Organic Quantum-Box Network Phys. Rev. Lett. 2013, 110, 086102
58. Li, Y.; Zhao, K.; Yang, Y.; Deng, K.; Zeng, Q.; Wang, C. Functionalization of Two-Component Molecular Networks: Recognition of Fe3+ Nanoscale 2011, 4, 148-151
59. Lobo-Checa, J.; Matena, M.; Muller, K.; Dil, J. H.; Meier, F.; Gade, L. H.; Jung, T. A.; Stohr, M. Band Formation from Coupled Quantum Dots Formed by a Nanoporous Network on a Copper Surface Science 2009, 325, 300-303