Thermodynamic controlled hierarchical assembly of ternary supramolecular networks at the liquid-solid interface

Chemistry - A European Journal

Volumn 15, Issue 22, 2009, Pages 5418-5423

  Li, Yibao ^a,b   Ma, Zhun ^c   Deng, Ke ^a   Lei, Shengbin ^a,d   Zeng, Qingdao ^a   Fan, Xiaolin ^b   De Feyter, Steven ^d   Huang, Wei ^c   Wang, Chen ^a  

^a NATIONAL CENTER FOR NANOSCIENCE AND TECHNOLOGY   (China)

^b GANNAN NORMAL UNIVERSITY   (China)

^c FUDAN UNIVERSITY   (China)

^d UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Networks; Scanning probe microscopy; Self assembly; Solid liquid interface

Indexed keywords

BUILDING BLOCK; CO-ADSORPTION; COMPLEX UNITS; CORONENE; HIERARCHICAL ASSEMBLIES; HYDROGEN BONDED NETWORK; LIQUID-SOLID INTERFACES; NETWORK STRUCTURES; NETWORKS; POROUS NETWORKS; SOLID-LIQUID INTERFACE; STRONG INTERACTION; SUPRAMOLECULAR NETWORKS; TRIMESIC ACID;

HYDROGEN; LIQUIDS; PROBES; SCANNING; SCANNING PROBE MICROSCOPY; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; THERMOANALYSIS; THERMODYNAMICS; TWO DIMENSIONAL;

PHASE INTERFACES;

EID: 66249104349     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900493     Document Type: Article

References (60)

1. S. De Feyter, F. C. De Schryver, Chem. Soc. Rev. 2003, 32, 139.
2. D. Bonifazi, A. Kiebele, M. Stöhr, F. Cheng, T. Jung, F. Diederich, H. Spillmann, Adv. Funct. Mater. 2007, 17, 1051.
3. a) G. Schull, L. Douillard, C. Fiorini-Debuisschert, F. Charra, F. Mathevet, D. Kreher, A. J. Attias, Nano Lett. 2006, 6, 1360;
4. b) K. Tahara, S. Furukawa, H. Uji-i, T. Uchino, T. Ichikawa, J. Zhang, W. Mamdouh, M. Sonoda, F. C. De Schryver, S. De Feyter, Y. Tobe, J. Am. Chem. Soc. 2006, 128, 16613;
5. c) S. Lei, K. Tahara, F. C. De Schryver, M. Van der Aueraer, Y. Tobe, S. De Deyter, Angew. Chem. 2008, 120, 3006;
6. Angew. Chem. Int. Ed. 2008, 47, 2964;
7. d) L. Merz, H. J. Güntherodt, L. J. Scherer, E. C. Constable, C. E. Housecroft, M. Neuburger, B. A. Hermann, Chem. Eur. J. 2005, 11, 2307.
8. a) J. A. Theobald, N. S. Oxtoby, M. A. Philips, N. R. Champness, P. H. Beton, Nature 2003, 424, 1029;
9. b) G. Pawin, K. L. Wong, K. Y. Kwon, L. Bartels, Science 2006, 313, 961;
10. c) M. Stöhr, M. Wahl, C. H. Galka, T. Riehm, T. A. Jung, L. H. Gade, Angew. Chem. 2005, 117, 7560;
11. Angew. Chem. Int. Ed. 2005, 44, 7394.
12. a) L. Kampschulte, M. Lackinger, A. K. Maier, R. S. K. Kishore, S. Griessl, M. Schmittel, W. M. Heckl, J. Phys. Chem. B 2006, 110, 10829;
13. b) S. J. H. Griessl, M. Lackinger, F. Jamitzky, T. Markert, M. Hietschold, W. M. Heckl, J. Phys. Chem. B 2004, 108, 11556
14. c) M. Ruben, D. Payer, A. Landa, A. Comisso, C. Gattinoni, N. Lin, J. P. Collin, J. P. Sauvage, A. De Vita, K. Kern, J. Am. Chem. Soc. 2006, 128, 15644.
15. a) J. Lu, S. B. Lei, Q. D. Zeng, S. Z. Kang, C. Wang, L. J. Wan, C. L. Bai, J. Phys. Chem. B 2004, 108, 5161;
16. b) X. H. Kong, K. Deng, Y. L. Yang, Q. D. Zeng, C. Wang, J. Phys. Chem. C 2007, 111, 9235;
17. c) D. X. Wu, K. Deng, Q. D. Zeng, C. Wang, J. Phys. Chem. B 2005, 109, 22296;
18. d) D. X. Wu, K. Deng, M. He, Q. D. Zeng, C. Wang, ChemPhysChem 2007, 8, 1519.
19. a) S. Stepanow, M. Lingenfelder, A. Dmitriev, H. Spillmann, E. Delvigne, N. Lin, X. Deng, C. Cai, J. V. Barth, K. Kern, Nat. Mater. 2004, 3, 229;
20. b) M. A. Lingenfelder, H. Spillmann, A. Dmitriev, S. Stepanow, N. Lin, J. V. Barth, K. Kern, Chem. Eur. J. 2004, 10, 1913.
21. a) N. Wintjes, D. Bonifazi, F. Cheng, A. Kiebele, M. Stöhr, T. Jung, H. Spillmann, F. Diederich, Angew. Chem. 2007, 119, 4167;
22. Angew. Chem. Int. Ed. 2007, 46, 4089;
23. b) M. Wahl, M. Stöhr, H. Spillmann, T. A. Jung, L. H. Gade, Chem. Commun. 2007, 1349.
24. a) A. Langner, S. L. Tait, N. Lin, C. Rajadurai, M. Ruben, K. Kern, Proc. Natl. Acad. Sci. USA 2007, 104, 17927;
25. b) M. Li, Y. L. Yang, K. Q. Zhao, Q. D. Zeng, C. Wang, J. Phys. Chem. C 2008, 112, 10141;
26. c) L. M. A. Perdigão, N. R. Champness, P.H. Beton, Chem. Commun. 2006, 538;
27. d) L. Kampschulte, T. L. Werblowsky, R. S. K. Kishore, M. Schmittel, W. M. Heckl, M. Lackinger, J. Am. Chem. Soc. 2008, 130, 8502.
28. Very recently some efforts have been made toward fabricating cova- lent 2D porous networks, but the ordering and symmetry is still not well controllable. For such works, see a) L. Grill, M. Dyer, L. Laffer- entz, M. Persson, M. V. Peters, S. Hecht, Nat. Nanotechnol. 2007, 2, 687;
29. b) S. Weigelt, C. Busse, C. Bombis, M. M. Knudsen, K. V. Gothelf, E. Lasgsgaard, F. B. Besenbachr, T. R. Linderoth, Angew. Chem. 2008, 120, 4478;
30. Angew. Chem. Int. Ed. 2008, 47, 4406;
31. c) M. Matena, T. Riehm, M Stöhr, T. A. Jung, L. H. Gade, Angew. Chem. 2008, 120, 2448;
32. Angew. Chem. Int. Ed. 2008, 47, 2414;
33. d) M. In't Veld, P. Iavicoli, S. Haq, D. B. Amabilino, R. Raval, Chem. Commun. 2008, 1536;
34. e) N. A. A. Zwaneveld, R. Pawlak, M. Abel, D. Catalin, D. Gigmes, D. Bertin, L. Porte, J. Am. Chem. Soc. 2008, 130, 6678.
35. a) D. Bléger, D. Kreher, F. Mathevet, A.-J. Attias, G. Schull, A. Huard, L. Douillard, C. Fiorini-Debuischert, F. Charra, Angew. Chem. 2007, 119, 7548;
36. Angew. Chem. Int. Ed. 2007, 46, 7404;
37. b) S. Furukawa, K. Tahara, F. C. De Schryver, M. Van der Auweraer, Y. Tobe, S. De Feyter, Angew. Chem. 2007, 119, 2889;
38. Angew. Chem. Int. Ed. 2007, 46, 2831;
39. c) S. Lei, K. Tahara, X. Feng, S. Furukawa, F. C. De Schryver, K. Müllen, Y. Tobe, S. De Feyter, J. Am. Chem. Soc. 2008, 130, 7119.
40. a) M. Blunt, X. Lin, M. D. Gimenez-Lopez, M. Schröder, N. R. Champness, P. H. Beton, Chem. Commun. 2008, 2304;
41. b) S. Lei, M. Surin, K. Tahara, J. Adisoejoso, R. Lazzaroni, Y. Tobe, S. De Feyter, Nano Lett. 2008, 8, 2541;
42. c) S. J. H. Griessl, M. Lackinger, F. Jamitzky, T. Markert, M. Hietschold, W. A. Heckl, Langmuir 2004, 20, 9403.
43. a) T. Classen, M. Lingenfelder, Y. Wang, R. Chopra, C. Virojanadara, U. Starke, G. Costantini, G. Fratesi, S. Fabris, S. de Gironcoli, S. Baroni, S. Haq, R. Raval, K. Kern, J. Phys. Chem. A 2007, 111, 12589;
44. b) S. V. Kolotuchin, P. A. Thiessen, E. E. Fenlon, S. R. Wilson, C. J. Loweth, S. C. Zimmerman, Chem. Eur. J. 1999, 5, 2537;
45. c) R. E. Melendez, C. V. K. Sharma, M. J. Zaworotko, C. Bauer, R. D. Rogers, Angew. Chem. 1996, 108, 2357;
46. Angew. Chem. Int. Ed. Engl. 1996, 35, 2213.
47. Y. Ye, W. Sun, Y. Wang, X. Shao, X. Xu, F. Cheng, J. Li, K. Wu, J. Phys. Chem. C 2007, 111, 10138.
48. S. Griessl, M. Lackinger, M. Edelwirth, M. Hietschold, W. M. Heckl, Single Mol. 2002, 3, 25.
49. a) Z. Ma, Y. Y. Wang, P. Wang, W. Huang, Y. B. Li, S. B. Lei, Y. L. Yang, X. L. Fan, C. Wang, ACS Nano 2007, 2, 160;
50. b) Y. B. Li, Z. Ma, G. C. Qi, Y. L. Yang, Q. D. Zeng, X. L. Fan, C. Wang, W. Huang, J. Phys. Chem. C 2008, 112, 8649.
51. S. B. Lei, C. Wang, S. X. Yin, H. N. Wang, F. Xi, H. W. Liu, B. Xu, L. J. Wan, C. L. Bai, J. Phys Chem. B 2001, 105, 10838.
52. N. Katsonis, E. Lacaze, B. L. Feringa, J. Mater. Chem. 2008, 18, 2065.
53. Z. C. Mu, L. J. Shu, H. Fuchs, M. Maytor, L. F. Chi, J. Am. Chem. Soc. 2008, 130, 10840.
54. U. Schlickum, R. Decker, F. Klappenberger, G. Zoppellaro, S. Klyatskaya, W. Auwärter, S. Neppl, K. Kern, H. Brune, M. Ruben, J. V. Barth, J. Am. Chem. Soc. 2008, 130, 11778.
55. -1 (see Ref. [12b]).
56. K. E. Plass, A. L. Grzesiak, A. J. Matzger, Acc. Chem. Res. 2007, 40, 287.
57. Note the composition in the monolayer at the interface is different from the composition in the solution, for instance, the mole ratio of TMA: StOF-COOH3: coronene for the sun-flower pattern is 12:6:1, while the mole ratio in the solution is 10:10:1.
58. Similar dependence on deposition sequence has been observed on other multi-component systems, see B. Xu, C. Tao, W. G. Cullen, J. E. Reutt-Robey, E. D. Williams, Nano Lett. 2005, 5, 2207.
59. L. Wang, Q. Chen, G. B. Pan, L. J. Wan, S. Zhang, X. Zhan, B. H. Northrop, P J. Stang, J. Am. Chem. Soc. 2008, 130, 13433.
60. Depending on the concentration of the components the concentration variation caused by adsorption could range from several up to more than 50 percent.