Two-Dimensional Nanoporous Networks Formed by Liquid-to-Solid Transfer of Hydrogen-Bonded Macrocycles Built from DNA Bases
Nerea Bilbao
Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain)
Search for more papers by this authorIris Destoop
Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven–University of Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium)
Search for more papers by this authorCorresponding Author
Prof. Steven De Feyter
Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven–University of Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium)
Steven De Feyter, Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven–University of Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium)
David González-Rodríguez, Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain)
Search for more papers by this authorCorresponding Author
Dr. David González-Rodríguez
Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain)
Steven De Feyter, Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven–University of Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium)
David González-Rodríguez, Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain)
Search for more papers by this authorNerea Bilbao
Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain)
Search for more papers by this authorIris Destoop
Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven–University of Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium)
Search for more papers by this authorCorresponding Author
Prof. Steven De Feyter
Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven–University of Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium)
Steven De Feyter, Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven–University of Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium)
David González-Rodríguez, Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain)
Search for more papers by this authorCorresponding Author
Dr. David González-Rodríguez
Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain)
Steven De Feyter, Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven–University of Leuven, Celestijnenlaan 200 F, 3001 Leuven (Belgium)
David González-Rodríguez, Nanostructured Molecular Systems and Materials Group, Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid (Spain)
Search for more papers by this authorGraphical Abstract
Abstract
We present an approach that makes use of DNA base pairing to produce hydrogen-bonded macrocycles whose supramolecular structure can be transferred from solution to a solid substrate. A hierarchical assembly process ultimately leads to two-dimensional nanostructured porous networks that are able to host size-complementary guests.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
anie_201509233_sm_miscellaneous_information.pdf4.6 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aJ. V. Barth, G. Costantini, K. Kern, Nature 2005, 437, 671–679;
- 1bF. Cicoira, C. Santato, F. Rosei, Top. Curr. Chem. 2008, 285, 203–267;
- 1cJ. A. A. W. Elemans, S. Lei, S. De Feyter, Angew. Chem. Int. Ed. 2009, 48, 7298–7332; Angew. Chem. 2009, 121, 7434–7469;
- 1dA. Ciesielski, C.-A. Palma, M. Bonini, P. Samori, Adv. Mater. 2010, 22, 3506–3520;
- 1eL. Bartels, Nat. Chem. 2010, 2, 87–95;
- 1fR. Otero, J. M. Gallego, A. L. Vázquez de Parga, N. Martín, R. Miranda, Adv. Mater. 2011, 23, 5148–5176;
- 1gM. El Garah, R. C. Perone, A. Santana Bonilla, S. Haar, M. Campitiello, R. Gutiérrez, G. Cuniberti, S. Masiero, A. Ciesielski, P. Samori, Chem. Commun. 2015, 51, 11677–11680;
- 1hP. Zalake, K. G. Thomas, Langmuir 2013, 29, 2242–2249.
- 2
- 2aT. Kudernac, S. Lei, J. A. A. W. Elemans, S. De Feyter, Chem. Soc. Rev. 2009, 38, 402–421;
- 2bK. S. Mali, J. Adisoejoso, E. Ghijsens, I. De Cat, S. De Feyter, Acc. Chem. Res. 2012, 45, 1309–1320;
- 2cT. Kudernac, A. K. Mandal, J. Huskens, Langmuir 2015, 31, 157–163.
- 3
- 3aC. Safarowsky, L. Merz, A. Rang, P. Broekmann, B. A. Hermann, C. A. Schalley, Angew. Chem. Int. Ed. 2004, 43, 1291–1294; Angew. Chem. 2004, 116, 1311–1314;
- 3bS. Yoshimoto, K. Suto, A. Tada, N. Kobayashi, K. Itaya, J. Am. Chem. Soc. 2004, 126, 8020–8027;
- 3cE. Mena-Osteritz, P. Bäuerle, Adv. Mater. 2006, 18, 447–451;
- 3dK. Tahara, J. Gotoda, C. N. Carroll, K. Hirose, S. De Feyter, Y. Tobe, Chem. Eur. J. 2015, 21, 6806–6816.
- 4
- 4aS. Stepanow, M. Lingenfelder, A. Dmitriev, H. Spillmann, E. Delvigne, N. Lin, X. Deng, C. Cai, J. V. Barth, K. Kern, Nat. Mater. 2004, 3, 229–233;
- 4bK. 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, 16613–16625;
- 4cM. O. Blunt, J. C. Russell, M. D. Giménez-Lopez, J. P. Garrahan, X. Lin, M. Schröder, N. R. Champness, P. H. Beton, Science 2008, 322, 1077–1081;
- 4dW. Xu, J. Wang, M. F. Jacobsen, M. Mura, M. Yu, R. E. A. Kelly, Q. Meng, E. Lægsgaard, I. Stensgaard, T. R. Linderoth, J. Kjems, L. N. Kantorovich, K. V. Gothelf, F. Besenbacher, Angew. Chem. Int. Ed. 2010, 49, 9373–9377; Angew. Chem. 2010, 122, 9563–9567.
- 5M. J. Mayoral, N. Bilbao, D. González-Rodríguez, ChemistryOpen 2015, DOI: 10.1002/open.201500171.
- 6See the Supporting Information for further details.
- 7
- 7aJ. Camacho-García, C. Montoro-García, A. M. López-Pérez, N. Bilbao, S. Romero-Pérez, D. González-Rodríguez, Org. Biomol. Chem. 2015, 13, 4506–4513;
- 7bN. Bilbao, V. Vázquez-González, M. Aranda, D. González-Rodríguez, Eur. J. Org. Chem. 2015, 32, 7160–7175.
- 8
- 8aC. Montoro-García, J. Camacho-García, A. M. López-Pérez, N. Bilbao, S. Romero-Pérez, M. J. Mayoral, D. González-Rodríguez, Angew. Chem. Int. Ed. 2015, 54, 6780–6784; Angew. Chem. 2015, 127, 6884–6888;
- 8bS. Romero-Pérez, J. Camacho-García, C. Montoro-García, A. M. López-Pérez, A. Sanz, M. J. Mayoral, D. González-Rodríguez, Org. Lett. 2015, 17, 2664–2667;
- 8cC. Montoro-García, J. Camacho-García, A. M. López-Pérez, M. J. Mayoral, N. Bilbao, D. González-Rodríguez, Angew. Chem. Int. Ed., DOI: 10.1002/anie.201508854; Angew. Chem., DOI: 10.1002/ange.201508854.
- 9Similar 2D arrangements were observed for other structurally related ditopic monomers; see: A. Llanes-Pallas, M. Matena, T. Jung, M. Prato, M. Stöhr, D. Bonifazi, Angew. Chem. Int. Ed. 2008, 47, 7726–7730; Angew. Chem. 2008, 120, 7840–7844.
- 10However, the reasons why GC2 tetramers prefer to bind through the purine edges are still not clear. Our hypothesis, developed in Figure S4, is that this particular arrangement may be a consequence of short-range cancelation of the nucleobase dipole moments, which are much stronger in the G-C pair than in the A-U pair; see: J. Sponer, J. Leszczynski, P. Hobza, Biopolymers 2001, 61, 3–31.
- 11
- 11aL. Pérez-García, D. B. Amabilino, Chem. Soc. Rev. 2007, 36, 941–967;
- 11bJ. Elemans, I. De Cat, H. Xu, S. De Feyter, Chem. Soc. Rev. 2009, 38, 722–736.