Controlling On-Surface Photoactivity: The Impact of π-Conjugation in Anhydride-Functionalized Molecules on a Semiconductor Surface

. 2024 Jul 22 ; 63 (30) : e202405983. [epub] 20240617

Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium print-electronic

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid38699982

Grantová podpora
no. 21-17194L Grantová Agentura České Republiky
CZ.02.01.01/00/22_010/0002906 Grantová Agentura České Republiky
no. 20-13692X Grantová Agentura České Republiky
CZ.10.03.01/00/22_003/0000048 European Union: REFRESH-Research Excellence For Region Sustainability and High-tech Industries
LM2023051 CzechNanoLab Research Infrastructure supported by MEYS CR
Grant# 202775 Swiss National Science Foundation - Switzerland

On-surface synthesis has become a prominent method for growing low-dimensional carbon-based nanomaterials on metal surfaces. However, the necessity of decoupling organic nanostructures from metal substrates to exploit their properties requires either transfer methods or new strategies to perform reactions directly on inert surfaces. The use of on-surface light-induced reactions directly on semiconductor/insulating surfaces represents an alternative approach to address these challenges. Here, exploring the photochemical activity of different organic molecules on a SnSe semiconductor surface under ultra-high vacuum, we present a novel on-surface light-induced reaction. The selective photodissociation of the anhydride group is observed, releasing CO and CO2. Moreover, we rationalize the relationship between the photochemical activity and the π-conjugation of the molecular core. The different experimental behaviour of two model anhydrides was elucidated by theoretical calculations, showing how the molecular structure influences the distribution of the excited states. Our findings open new pathways for on-surface synthesis directly on technologically relevant substrates.

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L. Grill, M. Dyer, L. Lafferentz, M. Persson, M. V. Peters, S. Hecht, Nat. Nanotechnol. 2007, 2, 687–691.

S. Clair, D. G. de Oteyza, Chem. Rev. 2019, 119, 4717–4776.

Q. Shen, H.-Y. Gao, H. Fuchs, Nano Today 2017, 13, 77–96.

J. I. Mendieta-Moreno, B. Mallada, B. de la Torre, T. Cadart, M. Kotora, P. Jelínek, Angew. Chem. Int. Ed. 2022, 61, e202208010.

J. Björk, C. Sánchez-Sánchez, Q. Chen, C. A. Pignedoli, J. Rosen, P. Ruffieux, X. Feng, A. Narita, K. Müllen, R. Fasel, Angew. Chem. Int. Ed. 2022, 61, e202212354.

E. Pérez-Elvira, A. Barragán, Q. Chen, D. Soler-Polo, A. Sánchez-Grande, D. J. Vicent, K. Lauwaet, J. Santos, P. Mutombo, J. I. Mendieta-Moreno, B. de la Torre, J. M. Gallego, R. Miranda, N. Martín, P. Jelínek, J. I. Urgel, D. Écija, Nat. Synth 2023, 1–12.

P. B. Bennett, Z. Pedramrazi, A. Madani, Y.-C. Chen, D. G. de Oteyza, C. Chen, F. R. Fischer, M. F. Crommie, J. Bokor, Appl. Phys. Lett. 2013, 103, 253114.

J. P. Llinas, A. Fairbrother, G. Borin Barin, W. Shi, K. Lee, S. Wu, B. Yong Choi, R. Braganza, J. Lear, N. Kau, W. Choi, C. Chen, Z. Pedramrazi, T. Dumslaff, A. Narita, X. Feng, K. Müllen, F. Fischer, A. Zettl, P. Ruffieux, E. Yablonovitch, M. Crommie, R. Fasel, J. Bokor, Nat. Commun. 2017, 8, 633.

Z. Chen, A. Narita, K. Müllen, Adv. Mater. 2020, 32, 2001893.

M. Kolmer, A. A. Ahmad Zebari, J. S. Prauzner-Bechcicki, W. Piskorz, F. Zasada, S. Godlewski, B. Such, Z. Sojka, M. Szymonski, Angew. Chem. Int. Ed. 2013, 52, 10300–10303.

M. Kittelmann, P. Rahe, M. Nimmrich, C. M. Hauke, A. Gourdon, A. Kühnle, ACS Nano 2011, 5, 8420–8425.

K. Sun, Y. Fang, L. Chi, ACS Materials Lett. 2021, 3, 56–63.

M. Lackinger, Dalton Trans. 2021, 50, 10020–10027.

H. D. Roth, Angew. Chem. Int. Ed. Engl. 1989, 28, 1193–1207.

F. Palmino, C. Loppacher, F. Chérioux, ChemPhysChem 2019, 20, 2271–2280.

A. Miura, S. De Feyter, M. M. S. Abdel-Mottaleb, A. Gesquière, P. C. M. Grim, G. Moessner, M. Sieffert, M. Klapper, K. Müllen, F. C. De Schryver, Langmuir 2003, 19, 6474–6482.

A. Richter, V. Haapasilta, C. Venturini, R. Bechstein, A. Gourdon, A. S. Foster, A. Kühnle, Phys. Chem. Chem. Phys. 2017, 19, 15172–15176.

D. Sloan, Y.-M. Sun, H. Ihm, J. M. White, J. Phys. Chem. B 1998, 102, 6825–6830.

A. Basagni, L. Ferrighi, M. Cattelan, L. Nicolas, K. Handrup, L. Vaghi, A. Papagni, F. Sedona, C. D. Valentin, S. Agnoli, M. Sambi, Chem. Commun. 2015, 51, 12593–12596.

Q. Shen, J. H. He, J. L. Zhang, K. Wu, G. Q. Xu, A. T. S. Wee, W. Chen, J. Chem. Phys. 2015, 142, 101902.

C. Nacci, M. Schied, D. Civita, E. Magnano, S. Nappini, I. Píš, L. Grill, J. Phys. Chem. C 2021, 125, 22554–22561.

H.-Y. Gao, D. Zhong, H. Mönig, H. Wagner, P.-A. Held, A. Timmer, A. Studer, H. Fuchs, J. Phys. Chem. C 2014, 118, 6272–6277.

L. Colazzo, F. Sedona, A. Moretto, M. Casarin, M. Sambi, J. Am. Chem. Soc. 2016, 138, 10151–10156.

L. Grossmann, B. T. King, S. Reichlmaier, N. Hartmann, J. Rosen, W. M. Heckl, J. Björk, M. Lackinger, Nat. Chem. 2021, 13, 730–736.

R. Lindner, P. Rahe, M. Kittelmann, A. Gourdon, R. Bechstein, A. Kühnle, Angew. Chem. Int. Ed. 2014, 53, 7952–7955.

C.-A. Palma, K. Diller, R. Berger, A. Welle, J. Björk, J. L. Cabellos, D. J. Mowbray, A. C. Papageorgiou, N. P. Ivleva, S. Matich, E. Margapoti, R. Niessner, B. Menges, J. Reichert, X. Feng, H. J. Räder, F. Klappenberger, A. Rubio, K. Müllen, J. V. Barth, J. Am. Chem. Soc. 2014, 136, 4651–4658.

F. Para, F. Bocquet, L. Nony, C. Loppacher, M. Féron, F. Cherioux, D. Z. Gao, F. Federici Canova, M. B. Watkins, Nat. Chem. 2018, 10, 1112–1117.

X. Zhang, F. Gärisch, Z. Chen, Y. Hu, Z. Wang, Y. Wang, L. Xie, J. Chen, J. Li, J. V. Barth, A. Narita, E. List-Kratochvil, K. Müllen, C.-A. Palma, Nat. Commun. 2022, 13, 442.

E. K. Fields, S. Meyerson, Chem. Commun. 1965, 474–476.

G. Porter, J. I. Steinfeld, J. Chem. Soc. A 1968, 877.

J. Lohmann, J. Chem. Soc. Faraday Trans. 1 1972, 68, 814.

H. A. Weimer, B. J. McFarland, S. Li, W. Weltner, J. Phys. Chem. 1995, 99, 1824–1825.

T. Sato, M. Moriyama, H. Niino, A. Yabe, Chem. Commun. 1999, 1089–1090.

T. Yatsuhashi, N. Nakashima, J. Phys. Chem. A 2000, 104, 203–208.

D. Pérez, D. Peña, E. Guitián, Eur. J. Org. Chem. 2013, 2013, 5981–6013.

F. Frezza, A. Sánchez-Grande, M. Ondráček, M. Vondráček, Q. Chen, O. Stetsovych, V. Villalobos-Vilda, E. Tosi, F. J. Palomares, M. F. López, C. Sánchez-Sánchez, K.-H. Ernst, J. A. Martín-Gago, J. Honolka, P. Jelínek, J. Phys. Condens. Matter 2023, 35, 335001.

A. L. Rheingold, R. L. Durney, J. Crystallogr. Spectrosc. Res. 1987, 17, 127–134.

M. V. Sulleiro, S. Quiroga, D. Peña, D. Pérez, E. Guitián, A. Criado, M. Prato, Chem. Commun. 2018, 54, 2086–2089.

Y. Zou, L. Kilian, A. Schöll, T. Schmidt, R. Fink, E. Umbach, Surf. Sci. 2006, 600, 1240–1251.

N. Pavliček, B. Schuler, S. Collazos, N. Moll, D. Pérez, E. Guitián, G. Meyer, D. Peña, L. Gross, Nature Chem 2015, 7, 623–628.

J. K. Fremerey, Vacuum 1999, 53, 197–201.

P. A. Redhead, AIP Conf. Proc. 2003, 671, 243–254.

T. H. Dunning Jr, J. Chem. Phys. 1989, 90, 1007–1023.

R. A. Kendall, T. H. Dunning Jr, R. J. Harrison, J. Chem. Phys. 1992, 96, 6796–6806.

S. E. Braslavsky, Pure Appl. Chem. 2007, 79, 293–465.

F. J. Giessibl, Rev. Sci. Instrum. 2019, 90, 011101.

I. Horcas, R. Fernández, J. M. Gómez-Rodríguez, J. Colchero, J. Gómez-Herrero, A. M. Baro, Rev. Sci. Instrum. 2007, 78, 013705.

M. Muntwiler, J. Zhang, R. Stania, F. Matsui, P. Oberta, U. Flechsig, L. Patthey, C. Quitmann, T. Glatzel, R. Widmer, E. Meyer, T. A. Jung, P. Aebi, R. Fasel, T. Greber, J. Synchrotron Radiat. 2017, 24, 354–366.

V. Blum, R. Gehrke, F. Hanke, P. Havu, V. Havu, X. Ren, K. Reuter, M. Scheffler, Comput. Phys. Commun. 2009, 180, 2175–2196.

J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865–3868.

A. Tkatchenko, M. Scheffler, Phys. Rev. Lett. 2009, 102, 073005.

A. D. Becke, J. Chem. Phys. 1993, 98, 5648–5652.

P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623–11627.

O. Krejčí, P. Hapala, M. Ondráček, P. Jelínek, Phys. Rev. B 2017, 95, 045407.

P. Hapala, G. Kichin, C. Wagner, F. S. Tautz, R. Temirov, P. Jelínek, Phys. Rev. B 2014, 90, 085421.

P. Hapala, R. Temirov, F. S. Tautz, P. Jelínek, Phys. Rev. Lett. 2014, 113, 226101.

A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571–2577.

A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829–5835.

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian 16, Revision C.01, Gaussian, Inc., Wallingford CT, 2016.

J. Schirmer, Phys. Rev. A 1982, 26, 2395–2416.

A. B. Trofimov, J. Schirmer, J. Phys. B 1995, 28, 2299.

S. G. Balasubramani, G. P. Chen, S. Coriani, M. Diedenhofen, M. S. Frank, Y. J. Franzke, F. Furche, R. Grotjahn, M. E. Harding, C. Hättig, A. Hellweg, B. Helmich-Paris, C. Holzer, U. Huniar, M. Kaupp, A. Marefat Khah, S. Karbalaei Khani, T. Müller, F. Mack, B. D. Nguyen, S. M. Parker, E. Perlt, D. Rappoport, K. Reiter, S. Roy, M. Rückert, G. Schmitz, M. Sierka, E. Tapavicza, D. P. Tew, C. van Wüllen, V. K. Voora, F. Weigend, A. Wodyński, J. M. Yu, J. Chem. Phys. 2020, 152, 184107.

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