Keywords
Advanced microscopies
Nanographenes
Atomic manipulation
Reactivity on surfaces
- Abstract 47
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Abstract
The integration of organic chemistry with surface science has enabled advances in the synthesis of nanographenes through the controlled fusion of benzenoid rings. Moreover, improvements in scanning probe microscopies have allowed the characterization of these nanostructures with submolecular resolution. Although on‑surface synthesis is still relatively recent, several transformations have been identified that provide access to fascinating structures. Most current methodologies employ thermally induced reactions promoted by metallic surfaces. However, existing strategies enable reactions on insulating surfaces, for example, through the application of voltage pulses from the microscope tip. This article highlights selected examples in this emerging scientific field at the interface between disciplines.
References
L. Gross, F. Mohn, N. Moll, P. Liljeroth, G. Meyer, Science 2009, 325, 1110-1114, https://doi.org/10.1126/science.1176210.
L. Gross, F. Mohn, N. Moll, B. Schuler, A. Criado, E. Guitián, D. Peña, A. Gourdon, G. Meyer, Science 2012, 337, 1326-1329, https://doi.org/10.1126/science.1225621.
S. Fatayer, F. Albrecht, Y. Zhang, D. Urbonas, D. Peña, N. Moll, L. Gross, Science 2019, 365. 142-145, https://doi.org/10.1126/science.aax5895.
L. Gross, B. Schuler, N. Pavliček, S. Fatayer, Z. Majzik, N. Moll, D. Peña, G. Meyer, Angew. Chem., Int. Ed. 2018, 57, 3888-3908, https://doi.org/10.1002/anie.201703509.
S.-W. Hla, L. Bartels, G. Meyer, K.-H. Rieder, Phys. Rev. Lett. 2000, 85, 2777-2780, https://doi.org/10.1002/anie.201703509.
F. Albrecht, S. Fatayer, I. Pozo, I. Tavernelli, J. Repp, D. Peña, L. Gross, Science 2022, 377, 298-301, https://doi.org/10.1126/science.abo6471.
L. Grill, M. Dyer, L. Lafferentz, M. Persson, M. V. Peters, S. Hecht, Nat. Nanotechnol. 2007, 2, 687-691, https://doi.org/10.1038/nnano.2007.346.
S. Clair, D. G. de Oteyza, Chem. Rev. 2019, 119, 4717-4776, https://doi.org/10.1021/acs.chemrev.8b00601.
C. Moreno, M. Vilas-Varela, B. Kretz, A. García-Leuke, M. V. Costache, M. Paradinas, M. Panighel, G. Ceballos, S. O. Valenzuela, D. Peña, A. Mugarza, Science 2018, 360, 199-203, https://doi.org/10.1126/science.aar2009.
Q. Fan, L. Yan, M. W. Tripp, O. Krejčí, S. Dimosthenous, S. R. Kachel, M. Chen, A. S. Foster, U. Koert, P. Liljeroth, J. M. Gottfried, Science 2021, 372, 852-856, https://doi.org/10.1126/science.abg4509.
Staab, H. A.; Diederich, F. Synthesis of Kekulene. Chem. Ber. 1983, 116, 3487-3503, https://doi.org/10.1002/cber.19831161021.
I. Pozo, Z. Majzik, N. Pavliček, M. Melle-Franco, E. Guitián, D. Peña, L. Gross, D. Pérez, J. Am. Chem. Soc. 2019, 141, 15488-15493, https://doi.org/10.1021/jacs.9b07926.
B. Schuler, S. Collazos, L. Gross, G. Meyer, D. Pérez, E. Guitián, D. Peña, Angew. Chem., Int. Ed. 2014, 53, 9004-9006, https://doi.org/10.1002/anie.201403707.
M. Vilas-Varela, S. Fatayer, Z. Majzik, D. Pérez, E. Guitián, L. Gross, D. Peña, Chem. Eur. J. 2018, 24, 17697-17700, https://doi.org/10.1002/chem.201805140.
I. Pozo, D. Pérez, D. Pérez en Molecular Nanographenes: Synthesis, Properties, and Applications, (Eds.: N. Martín, C. P. Nuckolls), Wiley, Germany, 2025, pp. 363-380, https://doi.org/10.1002/9783527845019.ch16.
R. S. Jassas, E. U. Mughal, A. Sadiq, R. I. Alsantali, M. M. Al-Rooqi, N. Naeem, Z. Moussa, S. A. Ahmed, RSC Adv. 2021, 11, 32158-32202, https://doi.org/10.1039/D1RA05910F.
K. Weiss, G. Beernink, F. Dötz, A. Birkner, K. Müllen C. H. Wöll, Angew. Chem., Int. Ed. 1999, 38, 3748-3752, https://doi.org/10.1002/(SICI)1521-3773(19991216)38:24<3748::AID-ANIE3748>3.3.CO;2-S.
M. Treier, C. A. Pignedoli, T. Laino, R. Rieger, K. Müllen, D. Passerone, R. Fasel, Nat. Chem. 2011, 3, 61-67, https://doi.org/10.1038/nchem.891.
R. Zuzak, I. Pozo, M. Engelund, A. Garcia-Lekue, M. Vilas-Varela, J. M. Alonso, M. Szymonski, E. Guitián, D. Pérez, S. Godlewski, D. Peña, Chem. Sci. 2019, 10, 10143-10148, https://doi.org/10.1039/C9SC03404H.
K. Xu, J. Urgel, K. Eimre, M. Di Giovannantonio, A. Keerthi, H. Komber S. Wang, A. Narita, R. Berger, P. Ruffieux, C. A. Pignedoli, J. Liu, K. Müllen, R. Fasel, X. Feng, J. Am. Chem. Soc. 2019, 141, 7726-7730, https://doi.org/10.1021/jacs.9b03554.
F. Ullmann, Justus Liebigs Ann. Chem. 1904, 332, 38-81, https://doi.org/10.1002/jlac.19043320104.
E. Charles, H. Sykes, Patrick Han, S. Alex Kandel, Kevin F. Kelly, Gregory S. McCarty, P. S. Weiss, Acc. Chem. Res. 2003, 36, 945-953, https://doi.org/10.1021/ar970286l.
S. Zint, D. Ebeling, T. Schlöder, S. Ahles, D. Mollenhauer, H. A. Wegner, A. Schirmeisen, ACS Nano 2017, 11, 4183-4190, https://doi.org/10.1021/acsnano.7b01109.
Q. Zhong, A. Ihle, S. Ahles, H. A. Wegner, A. Schirmeisen, D. Ebeling, Nat. Chem. 2021, 13, 1133-1139, https://doi.org/10.1038/s41557-021-00773-4.
J. Hieulle, E. Carbonell-Sanromà, M. Vilas-Varela, A. Garcia-Lekue, E. Guitián, D. Peña, J. I. Pascual, Nano Lett. 2018, 18, 418-423, https://doi.org/10.1021/acs.nanolett.7b04309.
J. Cai, P. Ruffieux, R. Jaafar, M. Bieri, T. Braun, S. Blankenburg, M. Muoth, A. P. Seitsonen, M. Saleh, X. Feng, K. Müllen, R. Fasel, Nature 2010, 466, 470-47, https://doi.org/10.1038/nature09211.
J. Lawrence, M. S. G. Mohammed, D. Rey, F. Aguilar-Galindo, A. Berdonces-Layunta, D. Peña, D. G. de Oteyza, ACS Nano 2021, 15, 4937-4946, https://doi.org/10.1021/acsnano.0c09756.
S. Kawai, K. Takahashi, S. Ito, R. Pawlak, T. Meier, P. Spijker, F. F. Canova, J. Tracey, K. Nozaki, A. S. Foster, E. Meyer, ACS Nano 2017, 11, 8122-8130, https://doi.org/10.1021/acsnano.7b02973.
C. Sánchez-Sánchez, A. Nicolaï, F. Rossel, J. Cai, J. Liu, X. Feng, K. Müllen, P. Ruffieux , R. Fasel, V. Meunier, J. Am. Chem. Soc. 2017, 139, 17617-17623, https://doi.org/10.1021/jacs.7b10026.
Z. Zeng, D. Guo, T. Wang, Q. Chen, A. Matěj, J. Huang, D. Han, Q. Xu, A. Zhao, P. Jelínek, D. G. de Oteyza, J.-S. McEwen, J. Zhu, J. Am. Chem. Soc. 2022, 144, 723-732, https://doi.org/10.1021/jacs.1c08284.
J. P. Calupitan, T. Wang, A. P. Paz, B. Álvarez, A. Berdonces-Layunta, P. Angulo-Portugal, R. Castrillo-Bodero, F. Schiller, D. Peña, M. Corso, D. Pérez, D. G. de Oteyza, J. Phys. Chem. Lett. 2023, 14, 947-953, https://doi.org/10.1021/acs.jpclett.2c03346.
Q. Fan, C. Wang, Y. Han, J. Zhu, W. Hieringer, J. Kuttner, G. Hilt, J. M. Gottfried, Angew. Chem., Int. Ed. 2013, 52, 4668-4672, https://doi.org/10.1002/anie.201300610.
A. Sánchez-Grande, B. de la Torre, J. Santos, B. Cirera, K. Lauwaet, T. Chutora, S. Edalatmanesh, P. Mutombo, J. Rosen, R. Zbořil, R. Miranda, J. Björk, P. Jelínek, N. Martín, D. Écija, Angew. Chem., Int. Ed. 2019, 58, 6559-6563, https://doi.org/10.1002/anie.201814154.
M. Liu, S. Li, J. Zhou, Z. Zha, J. Pan, X. Li, J. Zhang, Z. Liu, Y. Li, X. Qiu, ACS Nano 2018, 12, 12612-12618, https://doi.org/10.1021/acsnano.8b07349.
N. Pavliček, A. Mistry, Z. Majzik, N. Moll, G. Meyer, D. J. Fox, L. Gross, Nat. Nanotechnol. 2017, 12, 308-311, https://doi.org/10.1038/nnano.2016.305.
T. Wang, A. Berdonces-Layunta, N. Friedrich, M. Vilas-Varela, J. P. Calupitan, J. I. Pascual, D. Peña, D. Casanova, M. Corso, D. G. de Oteyza, J. Am. Chem. Soc. 2022, 144, 4522-4529, https://doi.org/10.1021/jacs.1c12618.
S. Mishra, D. Beyer, K. Eimre, J. Liu, R. Berger, O. Gröning, C. A. Pignedoli, K. Müllen, R. Fasel, X. Feng, P. Ruffieux, J. Am. Chem. Soc. 2019, 141, 10621-10625, https://doi.org/10.1021/jacs.9b05319.
J. Su, M. Telychko, P. Hu, G. Macam, P. Mutombo, H. Zhang, Y. Bao, F. Cheng, Z.-Q. Huang, Z. Qiu, S. J. R. Tan, H. Lin, P. Jelínek, F.-C. Chuang, J. Wu, J. Lu, Sci. Adv. 2019, 5, eaav7717, https://doi.org/10.1126/sciadv.aav7717.
S. Mishra, K. Xu, K. Eimre, H. Komber, J. Ma, C. A. Pignedoli, R. Fasel, X. Feng, P. Ruffieux, Nanoscale 2021, 13, 1624-1628, https://doi.org/10.1039/D0NR08181G.
J. Hieulle, S. Castro, N. Friedrich, A. Vegliante, F. R. Lara, S. Sanz, D. Rey, M. Corso, T. Frederiksen, J. I Pascual, D. Peña, Angew. Chem., Int. Ed. 2021, 60, 25224-25229, https://doi.org/10.1002/anie.202108301.
J. Krüger, F. García, F. Eisenhut, D. Skidin, J. M. Alonso, E. Guitián, D. Pérez, G. Cuniberti, F. Moresco, D. Peña, Angew. Chem., Int. Ed. 2017, 56, 11945-11948, https://doi.org/10.1002/anie.201706156.
F. Eisenhut, T. Kühne, F. García, S. Fernández, E. Guitián, D. Pérez, G. Trinquier, G. Cuniberti, C. Joachim, D. Peña, F. Moresco, ACS Nano 2020, 14, 1011-1017, https://doi.org/10.1021/acsnano.9b08456.
R. Zuzak, M. Kumar, O. Stoica, D. Soler-Polo, J. Brabec, K. Pernal, L. Veis, R. Blieck, A. M. Echavarren, P. Jelinek, S. Godlewski, Angew. Chem., Int. Ed. 2024, 63, e202317091, https://doi.org/10.1002/anie.202317091.
Z. Ruan, J. Schramm, J. B. Bauer, T. Naumann, L. V. Müller, F. Sättele, H. F. Bettinger, R. Tonner-Zech, J. M. Gottfried, J. Am. Chem. Soc. 2025, 147, 4862-4870, https://doi.org/10.1021/jacs.4c13296.
J. Besteiro-Sáez, L. M. Mateo, S. Salaverría, T. Wang, P. Angulo-Portugal, J. P. Calupitan, J. Rodríguez-Fernández, A. García-Fuente, J. Ferrer, D. Pérez, M. Corso, D. G. de Oteyza, D. Peña, Angew. Chem., Int. Ed. 2024, 63, e202411861, https://doi.org/10.1002/anie.202411861.
M. Zugermeier, M. Gruber, M. Schmid, B. P. Klein, L. Ruppenthal,P. Müller, R. Einholz, W. Hieringer, R. Berndt, H. F. Bettinger, J. Michael Gottfried, Nanoscale 2017, 9, 12461-12469, https://doi.org/10.1039/C7NR04157H.
J. I. Urgel, S. Mishra, H. Hayashi, J. Wilhelm, C. A. Pignedoli, M. Di Giovannantonio, R. Widmer, M. Yamashita, N. Hieda, P. Ruffieux, H. Yamada, R. Fasel, Nat. Commun. 2019, 10, 861, https://doi.org/10.1038/s41467-019-08650-y.
J. Castro-Esteban, F. Albrecht, S. Fatayer, D. Pérez, L. Gross, D. Peña, Angew. Chem., Int. Ed. 2021, 60, 26346-26350, https://doi.org/10.1002/anie.202110311.
Q. Fan, D. Martin-Jimenez, S. Werner, D. Ebeling, T. Koehler, T. Vollgraff, J. Sundermeyer, W. Hieringer, A. Schirmeisen, J. M. Gottfried, J. Am. Chem. Soc. 2020, 142, 894-899, https://doi.org/10.1021/jacs.9b10151.
M. Di Giovannantonio, X. Yao, K. Eimre, J. I. Urgel, P. Ruffieux, C. A. Pignedoli, K. Müllen, R. Fasel, A. Narita, J. Am. Chem. Soc. 2020, 142, 12046-12050, https://doi.org/10.1021/jacs.0c05268.
I. C.-Y. Hou, Q. Sun, K. Eimre, M. Di Giovannantonio, J. I. Urgel, P. Ruffieux, A. Narita, R. Fasel, K. Müllen, J. Am. Chem. Soc. 2020, 142, 10291-10296, https://doi.org/10.1021/jacs.0c03635.
F. Xiang, S. Maisel, S. Beniwal, V. Akhmetov, C. Ruppenstein, M. Devarajulu, A. Dörr, O. Papaianina, A. Görling, K. Y. Amsharov, S. Maier, Nat. Chem. 2022, 14, 871-876, https://doi.org/10.1038/s41557-022-00968-3.
R. Zuzak, P. Dabczynski, J. Castro-Esteban, J. I. Martínez, M. Engelund, D. Pérez, D. Peña, S. Godlewski, Nat. Commun. 2025, 16, 691, https://doi.org/10.1038/s41467-024-54774-1.
K. Biswas, J. Janeiro, A. Gallardo, M. Lozano, A. Barragán, B. Álvarez, D. Soler-Polo, O. Stetsovych, A. P. Solé, K. Lauwaet, J. M. Gallego, D. Pérez, R. Miranda, J. I. Urgel, P. Jelínek, D. Peña, D. Écija, Nat. Synth. 2025, 4, 233-242, https://doi.org/10.1038/s44160-024-00665-8.
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