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

Author:

Frezza Federico12ORCID,Sánchez‐Grande Ana1ORCID,Canola Sofia1ORCID,Lamancová Anna3,Mutombo Pingo1ORCID,Chen Qifan1,Wäckerlin Christian45,Ernst Karl‐Heinz16ORCID,Muntwiler Matthias5ORCID,Zema Nicola7,Di Giovannantonio Marco7ORCID,Nachtigallová Dana38,Jelínek Pavel1ORCID

Affiliation:

1. Institute of Physics Czech Academy of Sciences Cukrovarnická 10 16200 Prague 6 Czech Republic

2. Faculty of Nuclear Sciences and Physical Engineering Czech Technical University in Prague Břehová 78/7 11519 Prague 1 Czech Republic

3. Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo námĕstí 542/2 160 00 Prague Czech Republic

4. Institute of Physics Swiss Federal Institute of Technology Lausanne (EPFL) CH-1015 Lausanne Switzerland

5. Paul Scherrer Institute (PSI) 5232 Villigen PSI Switzerland

6. Empa, Swiss Federal Laboratories for Materials Science and Technology 8600 Dübendorf Switzerland

7. CNR - Istituto di Struttura della Materia (CNR-ISM) via Fosso del Cavaliere 100 00133 Rome Italy

8. IT4Innovations VŠB-Technical University of Ostrava 17. listopadu 2172/15 708 00 Ostrava-Poruba Czech Republic

Abstract

AbstractOn‐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.

Funder

Grantová Agentura České Republiky

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Publisher

Wiley

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