An Electron-Rich Cyclic (Alkyl)(Amino)Carbene on Au(111), Ag(111), and Cu(111) Surfaces

Anne Bakker; Matthias Freitag; Elena Kolodzeiski; Peter Bellotti; Alexander Timmer; Jindong Ren; Bertram Schulze Lammers; Daniel Moock; Herbert W Roesky; Harry Mönig; Saeed Amirjalayer; Harald Fuchs; Frank Glorius

doi:10.1002/anie.201915618

An Electron-Rich Cyclic (Alkyl)(Amino)Carbene on Au(111), Ag(111), and Cu(111) Surfaces

Angew Chem Int Ed Engl. 2020 Aug 3;59(32):13643-13646. doi: 10.1002/anie.201915618. Epub 2020 Jun 3.

Authors

Anne Bakker^{1

2}, Matthias Freitag³, Elena Kolodzeiski^{1

2

4}, Peter Bellotti³, Alexander Timmer^{1

2

5}, Jindong Ren^{1

2}, Bertram Schulze Lammers^{1

2}, Daniel Moock³, Herbert W Roesky⁶, Harry Mönig^{1

2}, Saeed Amirjalayer^{1

2

4}, Harald Fuchs^{1

2}, Frank Glorius³

Affiliations

¹ Physikalisches Institut, Westfälische Wilhelms-Universität, Wilhelm-Klemm-Strasse 10, 48149, Münster, Germany.
² Center for Nanotechnology, Heisenbergstrasse 11, 48149, Münster, Germany.
³ Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149, Münster, Germany.
⁴ Center for Multiscale Theory and Computation, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149, Münster, Germany.
⁵ nanoAnalytics GmbH, Heisenbergstrasse 11, 48149, Münster, Germany.
⁶ Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077, Göttingen, Germany.

Abstract

The structural properties and binding motif of a strongly σ-electron-donating N-heterocyclic carbene have been investigated on different transition-metal surfaces. The examined cyclic (alkyl)(amino)carbene (CAAC) was found to be mobile on surfaces, and molecular islands with short-range order could be found at high coverage. A combination of scanning tunneling microscopy (STM), X-ray photoelectron spectroscopy (XPS), and density functional theory (DFT) calculations highlights how CAACs bind to the surface, which is of tremendous importance to gain an understanding of heterogeneous catalysts bearing CAACs as ligands.

Keywords: CAAC; X-ray photoelectron spectroscopy; gold surfaces; ligands; scanning probe microscopy.

Abstract

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