Switchable Self-Assembly of a Bioinspired Alkyl Catechol at a Solid/Liquid Interface: Competitive Interfacial, Noncovalent, and Solvent Interactions
Javier Saiz-Poseu
Centro de Investigación en Nanociencia y Nanotecnología (ICN-CSIC), Esfera UAB, Edificio CM7, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain), Fax: (+34) 935813717
Fundación Privada ASCAMM, Unidad de Nanotecnología (NANOMM), Parc Tecnològic del Vallès, Av. Universitat Autònoma, 23-08290, Cerdanyola del Vallès, Barcelona (Spain)
Search for more papers by this authorDr. Jordi Faraudo
Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus de la UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Search for more papers by this authorAntoni Figueras
Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Search for more papers by this authorDr. Ramon Alibes
Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Search for more papers by this authorCorresponding Author
Dr. Felix Busqué
Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Felix Busqué, Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Daniel Ruiz-Molina, Centro de Investigación en Nanociencia y Nanotecnología (ICN-CSIC), Esfera UAB, Edificio CM7, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain), Fax: (+34) 935813717
Search for more papers by this authorCorresponding Author
Dr. Daniel Ruiz-Molina
Centro de Investigación en Nanociencia y Nanotecnología (ICN-CSIC), Esfera UAB, Edificio CM7, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain), Fax: (+34) 935813717
Felix Busqué, Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Daniel Ruiz-Molina, Centro de Investigación en Nanociencia y Nanotecnología (ICN-CSIC), Esfera UAB, Edificio CM7, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain), Fax: (+34) 935813717
Search for more papers by this authorJavier Saiz-Poseu
Centro de Investigación en Nanociencia y Nanotecnología (ICN-CSIC), Esfera UAB, Edificio CM7, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain), Fax: (+34) 935813717
Fundación Privada ASCAMM, Unidad de Nanotecnología (NANOMM), Parc Tecnològic del Vallès, Av. Universitat Autònoma, 23-08290, Cerdanyola del Vallès, Barcelona (Spain)
Search for more papers by this authorDr. Jordi Faraudo
Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus de la UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Search for more papers by this authorAntoni Figueras
Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Search for more papers by this authorDr. Ramon Alibes
Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Search for more papers by this authorCorresponding Author
Dr. Felix Busqué
Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Felix Busqué, Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Daniel Ruiz-Molina, Centro de Investigación en Nanociencia y Nanotecnología (ICN-CSIC), Esfera UAB, Edificio CM7, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain), Fax: (+34) 935813717
Search for more papers by this authorCorresponding Author
Dr. Daniel Ruiz-Molina
Centro de Investigación en Nanociencia y Nanotecnología (ICN-CSIC), Esfera UAB, Edificio CM7, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain), Fax: (+34) 935813717
Felix Busqué, Department de Química, Universitat Autònoma de Barcelona, Edifici C, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain)
Daniel Ruiz-Molina, Centro de Investigación en Nanociencia y Nanotecnología (ICN-CSIC), Esfera UAB, Edificio CM7, Campus UAB, 08193, Cerdanyola del Vallès, Barcelona (Spain), Fax: (+34) 935813717
Search for more papers by this authorGraphical Abstract
Recognized strong adhesion and organization of catechols on surfaces has been used as a means to study the main parameters that control molecular self-assembly processes on surfaces, namely, the energetics (molecule/molecule, molecule/surface interactions) and thermodynamics (solvent effects; see figure). This knowledge is used to establish temperature-induced switchable 2D supramolecular structures
Abstract
The large tendency of catechol rings to adsorb on surfaces has been studied by STM experiments with molecular resolution combined with molecular-dynamics simulations. The strong adhesion is due to interactions with the surface and solvent effects. Moreover, the thermodynamic control over the differential adsorption of 1 and the nonanoic solvent molecules has been used to induce a new temperature-induced switchable interconversion. Two different phases that differ in their crystal packing and the presence of solvent molecules coexist upon an increase or decrease in the temperature. These results open new insight into the behavior of catechol molecules on surfaces and 2D molecular suprastructures.
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References
- 1H. Lee, N. F. Scherer, P. B. Messersmith, Proc. Natl. Acad. Sci. USA 2006, 103, 12999–13003.
- 2M. J. Sever, J. T. Weisser, J. Monahan, S. Srinivasan, J. J. Wilker, Angew. Chem. 2004, 116, 454–456;
10.1002/ange.200352759 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 448–450.
- 3
- 3aY. Kuraku in Urushi: Proceedings of the Urushi Study Group (Eds.: ), Getty Conservation Institute, California, USA, 1988, pp. 45–51;
- 3bE. J. Kidder, Ancient People and Places, Thames and Hudson, Japan, 1959.
- 4J. Kumanotani, Prog. Org. Coat. 1995, 26, 163–195.
- 5R. Lu, Y. Kamiya, T. Miyakoshi, Talanta 2006, 70, 370–376.
- 6
- 6aY. Lee, H. J. Cheng, S. Yeo, C.-H. Ahn, H. Lee, P. B. Messersmith, T. G. Park, Soft Matter 2010, 6, 977–983;
- 6bS. A. Burke, M. Ritter-Jones, B. P. Lee, P. B. Messersmith, Biomed. Mater. 2007, 2, 203–210;
- 6cH. Lee, B. P. Lee, P. B. Messersmith, Nature 2007, 448, 338–341;
- 6dB. P. Lee, C.-Y. Chao, F. N. Nunalee, E. Motan, K. R. Shull, P. B. Messersmith, Macromolecules 2006, 39, 1740–1748;
- 6eM. Yu, T. J. Deming, Macromolecules 1998, 31, 4739–4745.
- 7
- 7aJ. Xia, Y. Xu, J. Lin, Prog. Org. Coat. 2010, 67, 365–369;
- 7bH. S. Kim, J. H. Yeum, S. W. Choi, J. Y. Lee, I. W. Cheong, Prog. Org. Coat. 2009, 65, 341–347;
- 7cJ. Xia, Y. Xu, B. Hu, J. Lin, Prog. Org. Coat. 2009, 65, 510–513;
- 7dH. Lee, S. M. Dellatore, W. M. Miller, P. B. Messersmith, Science 2007, 318, 426–430.
- 8
- 8aN. Henningsen, R. Rurali, C. Limbach, R. Drost, J. I. Pascual, K. J. Franke, J. Phys. Chem. Lett. 2011, 2, 55–61;
- 8bW. Essolaani, F. Picaud, C. Ramseyer, P. Gambardella, M. Saïd, D. Spanjaard, M.-C. Desjonquères, Surf. Sci. 2011, 605, 917–922;
- 8cA. Mugarza, N. Lorente, P. Ordejón, C. Krull, S. Stepanow, M.-L. Bocquet, J. Fraxedas, G. Ceballos, P. Gambardella, Phys. Rev. Lett. 2010, 105, 115702;
- 8dS. Stepanow, J. Honolka, P. Gambardella, L. Vitali, N. Abdurakhmanova, T-C. Tseng, S. Rauschenbach, S. L. Tait, V. Sessi, S. Klyatskaya, M. Ruben, K. Kern, J. Am. Chem. Soc. 2010, 132, 11900–11901;
- 8eU. Schlickum, F. Klappenberger, R. Decker, G. Zoppellaro, S. Klyatskaya, M. Ruben, K. Kern, H. Brune, J. V. Barth, J. Phys. Chem. C 2010, 114, 15602–15606;
- 8fT. Suzuki, T. Lutz, D. Payer, N. Lin, S. L. Tait, G. Costantini, K. Kernae, Phys. Chem. Chem. Phys. 2009, 11, 6498–6504;
- 8gJ. Y. Park, Y. Qi, I. Ratera, M. Salmeron, J. Chem. Phys. 2008, 128, 234701;
- 8hM. Tatarkhanov, E. Fomin, M. Salmeron, K. Andersson, H. Ogasawara, L. G. M. Pettersson, A. Nilsson, J. I. Cerdá, J. Chem. Phys. 2008, 129, 154109;
- 8iU. 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, 11778–11782;
- 8jS. L. Tait, A. Langner, N. Lin, R. Chandrasekar, O. Fuhr, M. Ruben, K. Kern, ChemPhysChem 2008, 9, 2495–2499;
- 8kF. Klappenberger, M. E. Cañas- Ventura, S. Clair, S. Pons, U. Schlickum, Z.-R. Qu, T. Strunskus, A. Comisso, C. Wöll, H. Brune, K. Kern, A. De Vita, M. Ruben, J. V. Barth, ChemPhysChem 2008, 9, 2522–2530;
- 8lP. Cabrera-Sanfelix, D. Sánchez-Portal, A. Mugarza, T. K. Shimizu, M. Salmeron, A. Arnau, Phys. Rev. B 2007, 76, 205438;
- 8mN. Lin, A. Langner, S. L. Tait, C. Rajadurai, M. Ruben, K. Kern, Chem. Commun. 2007, 4860–4862;
- 8nM. 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, 15644–15651;
- 8oN. Henningsen, K. J. Franke, I. F. Torrente, G. Schulze, B. Priewisch, K. Ruck-Braun, J. Dokić, T. Klamroth, P. Saalfrank, J. I. Pascual, J. Phys. Chem. C 2007, 111, 14843–14848;
- 8pA. Dmitriev, H. Spillmann, S. Stepanow, T. Strunskus, C. Wöll, A. P. Seitsonen, M. Lingenfelder, N. Lin, J. V. Barth, K. Kern, ChemPhysChem 2006, 7, 2197–2204;
- 8qE. Barrena, E. Palacios- Lidón, C. Munuera, X. Torrelles, S. Ferrer, U. Jonas, M. Salmeron, C. Ocal, J. Am. Chem. Soc. 2004, 126, 385–395;
- 8rP. Gambardella, M. Blanc, H. Brune, K. Kuhnke, K. Kern, Phys. Rev. B 2000, 61, 2254.
- 9
- 9aL.-M. Liu, S.-C. Li, H. Cheng, U. Diebold, A. Selloni, J. Am. Chem. Soc. 2011, 133, 7816–7823;
- 9bS.-C. Li, L.-N. Chu, X.-Q. Gong, U. Diebold, Science 2010, 328, 882–884;
- 9cS.-C. Li, J.-G. Wang, P. Jacobson, X.-Q. Gong, A. Selloni, U. Diebold, J. Am. Chem. Soc. 2009, 131, 980–984;
- 9dM. Weinhold, S. Soubatch, R. Temirov, M. Rohlfing, B. Jastorff, F. S. Tautz, C. Doose, J. Phys. Chem. B 2006, 110, 23756–23769;
- 9eG.-X. Wei, G.-B. Pan, L.-J. Wan, J.-C. Zhao, C.-L. Bai, Surf. Sci. 2002, 520, L625L632.
- 10
- 10aJ. Visser, N. Katsonis, J. Vicario, B. L. Feringa, Langmuir 2009, 25, 5980–5985;
- 10bN. Katsonis, A. Marchenko, D. Fichou, N. Barrett, Surf. Sci. 2008, 602, 9–16;
- 10cS. Lei, K. Tahara, F. C. De Schryver, M. Van der Auweraer, Y. Tobe, S. De Feyter, Angew. Chem. 2008, 120, 3006–3010; Angew. Chem. Int. Ed. 2008, 47, 2964–2968;
- 10dN. Katsonis, E. Lacaze, B. L. Feringa, J. Mater. Chem. 2008, 18, 2065–2073;
- 10eA. Nion, P. Jiang, A. Popoff, D. Fichou, J. Am. Chem. Soc. 2007, 129, 2450–2451;
- 10fS. Furukawa, K. Tahara, F. C. De Schryver, M. Van der Auweraer, Y. Tobe, S. De Feyter, Angew. Chem. 2007, 119, 2889–2892; Angew. Chem. Int. Ed. 2007, 46, 2831–2834;
- 10gN. Katsonis, J. Vicario, T. Kudernac, J. Visser, M. M. Pollard, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 15537–15541;
- 10hM. Lackinger, S. Griessl, W. M. Heckl, M. Hietschold, G. W. Flynn, Langmuir 2005, 21, 4984–4988;
- 10iM. M. S. Abdel-Mottaleb, N. Schuurmans, S. de Feyter, J. Van Esch, B. L. Feringa, F. C. de Schryver, Chem. Commun. 2002, 1894–1895;
- 10jA. Marchenko, N. Katsonis, D. Fichou, C. Aubert, M. Malacria, J. Am. Chem. Soc. 2002, 124, 9998–9999.
- 11
- 11aA. Jefferson, M. V. Sargent, S. Wangchareontrakul, Aust. J. Chem. 1988, 41, 19–25;
- 11bA. Groweiss, J. H. Cardellina II, L. K. Pannell, D. Uyakul, Y. Kashman, M. R. Boyd, J. Nat. Prod. 1997, 60, 116–121.
- 12
- 12aX. Zhang, Q. Chen, G.-J. Deng, Q.-H. Fan, L.-J. Wan, J. Phys. Chem. C 2009, 113, 16193–16198;
- 12bF. Tao, J. Goswami, S. L. Bernasek, J. Phys. Chem. B 2006, 110, 195662–19569.
- 13D. Rohde, C.-J. Yan, H.-J. Yan, L.-J. Wan, Angew. Chem. 2006, 118, 4100–4104;
10.1002/ange.200600725 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 3996–4000.
- 14M. Lang, W. Stelich, Synthesis 2005, 6, 1019–1027.
- 15J. C. Phillips, R. Braun, W. Wang, J. Gumbart, E. Tajkhorshid, E. Villa, C. Chipot, R. D. Skeel, L. Kale, K. Schulten, J. Comput. Chem. 2005, 26, 1781–1802.
- 16A. D. MacKerell Jr., M. Feig, C. L. III Brooks, J. Comput. Chem. 2004, 25, 1400–1415.
- 17C. D. Lorenz, J. Faraudo, A. Travesset, Langmuir 2008, 24, 1654–1658.
- 18J. Hénin, J. Fiorin, C. Chipot, M. L. Klein, J. Chem. Theory Comput. 2010, 6, 35–47.